Abstract
The catalytic addition of water to alkynes (hydration) generates valuable carbonyl
compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts
hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research
has been devoted to finding catalysts based on less toxic metals, the most promising
being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov
hydration of terminal alkynes to aldehydes has been realized in an efficient manner
with ruthenium(II) complex catalysts. The present review article lists known hydration
catalysts and discusses applications of catalytic hydration to different classes of
substrates, with an emphasis on functional group tolerance and regioselectivity.
-
1 Introduction
-
2 Timeline
-
3 Alkyne Hydration Catalysts
-
3.1 Brønsted Acid and Base Catalysts
-
3.2 Mercury Catalysts
-
3.3 Non-Mercurial Catalysts for Alkyne Hydration
-
3.4 Anti-Markovnikov Hydration of Terminal Alkynes
-
3.5 Enzymatic Hydration of Alkynes
-
4 Mechanisms of Catalytic Alkyne Hydration
-
4.1 Brønsted Acid Catalyzed Hydration
-
4.2 Mercury-Catalyzed Hydration
-
4.3 Other-Metal-Catalyzed Markovnikov Hydrations
-
4.4 Mechanism of Ruthenium-Catalyzed Anti-Markovnikov Hydration
-
5 Substrate Spectrum and Selectivity of Catalytic Alkyne Hydration
-
5.1 Markovnikov Hydration Catalysis
-
5.2 Anti-Markovnikov Hydration Catalysts
-
6 Reactions Related to Catalytic Alkyne Hydration
-
7 Conclusions and Outlook
Key words
alkynes - catalysis - hydration - ketones - aldehydes
References
<A NAME="RE17407SS-1">1</A> Classification according to:
Jones RAY.
Bunnett JF.
Pure Appl. Chem.
1989,
61:
725
<A NAME="RE17407SS-2">2</A>
Trost BM.
Science
1991,
254:
1471
<A NAME="RE17407SS-3">3</A>
Thermodynamic values calculated with data from:
http://webbook.nist.gov/chemistry/ (accessed January 2007). Note that phase-changes
will affect ΔrG/ΔrH.
<A NAME="RE17407SS-4">4</A>
Zweifel G.
Brown HC.
Org. React.
1963,
13:
1
<A NAME="RE17407SS-5">5</A>
Oestreich M. In Science of Synthesis
Vol. 25:
Brückner R.
Thieme;
Stuttgart:
2006.
p.199
<A NAME="RE17407SS-6A">6a</A>
Figadère B.
Franck X. In Science of Synthesis
Vol. 26:
Cossy J.
Thieme;
Stuttgart:
2004.
p.401
<A NAME="RE17407SS-6B">6b</A>
Stetter H. In Houben-Weyl
4th ed., Vol. VII/2a:
Müller E.
Thieme;
Stuttgart:
1973.
p.816
<A NAME="RE17407SS-7A">7a</A>
Alonso F.
Beletskaya IP.
Yus M.
Chem. Rev.
2004,
104:
3079
<A NAME="RE17407SS-7B">7b</A>
Beller M.
Seayad J.
Tillack A.
Jiao H.
Angew. Chem. Int. Ed.
2004,
43:
3368
<A NAME="RE17407SS-8">8</A>
Tani K.
Kataoka Y. In
Catalytic Heterofunctionalization
Togni A.
Grützmacher H.
Wiley-VCH;
Weinheim:
2001.
p.171
<A NAME="RE17407SS-9">9</A>
Miocque M.
Hung NM.
Yen VQ.
Ann. Chim.
1963,
8:
157
<A NAME="RE17407SS-10">10</A>
Petrov AD.
Uspekhi Khimii
1952,
21:
250
<A NAME="RE17407SS-11">11</A>
Jäger V.
Viehe HG.
Houben-Weyl
4th ed., Vol. V/2a:
Müller E.
Thieme;
Stuttgart:
1977.
p.726
<A NAME="RE17407SS-12">12</A>
Hudrlik PF.
Hudrlik AM. In
The Chemistry of the Carbon-Carbon Triple Bond
Patai S.
John Wiley & Sons;
Chichester:
1978.
p.240
<A NAME="RE17407SS-13">13</A>
Rutledge TF.
Acetylenes and Allenes
Reinhold Book Corporation;
New York:
1969.
<A NAME="RE17407SS-14">14</A>
Winterfeldt E. In
Chemistry of Acetylenes
Viehe HG.
Marcel Dekker;
New York:
1969.
p.267
<A NAME="RE17407SS-15">15</A>
Raphael RA.
Acetylenic Compounds in Organic Synthesis
Butterworths;
London:
1955.
<A NAME="RE17407SS-16">16</A>
Berthelot M.
Ann. Chim. Phys.
1863,
67:
52
<A NAME="RE17407SS-17">17</A>
Lagermarck H.
Eltekoff A.
Chem. Ber.
1877,
10:
637
<A NAME="RE17407SS-18">18</A>
Fittig R.
Schrohe A.
Chem. Ber.
1875,
8:
367
<A NAME="RE17407SS-19A">19a</A>
Kutscheroff M.
Chem. Ber.
1881,
14:
1540
<A NAME="RE17407SS-19B">19b</A>
Kutscheroff M.
Chem. Ber.
1884,
17:
13
<A NAME="RE17407SS-20">20</A>
Moiseev II.
Kinet. Catal.
2001,
42:
1
<A NAME="RE17407SS-21">21</A>
Neumann B.
Schneider H.
Angew. Chem.
1920,
33:
189
<A NAME="RE17407SS-22">22</A>
Acetylene, In Ullmann’s Encyclopedia of Industrial Chemistry
7th ed.:
Wiley-VCH;
Weinheim:
2006.
<A NAME="RE17407SS-23">23</A>
Hester AS.
Himmler K.
Ind. Eng. Chem.
1959,
51:
1424
<A NAME="RE17407SS-24">24</A>
Thomas RJ.
Campbell KN.
Hennion GF.
J. Am. Chem. Soc.
1938,
60:
718
<A NAME="RE17407SS-25A">25a</A>
Reppe W.
Liebigs Ann. Chem.
1948,
560:
1
<A NAME="RE17407SS-25B">25b</A>
Reppe W.
Liebigs Ann. Chem.
1953,
582:
1
<A NAME="RE17407SS-25C">25c</A>
Reppe W.
Liebigs Ann. Chem.
1955,
596:
1
<A NAME="RE17407SS-25D">25d</A>
Reppe W.
Liebigs Ann. Chem.
1955,
596:
25
<A NAME="RE17407SS-25E">25e</A>
Reppe W.
Liebigs Ann. Chem.
1955,
596:
38
<A NAME="RE17407SS-25F">25f</A>
Reppe W.
Liebigs Ann. Chem.
1956,
601:
81
<A NAME="RE17407SS-26">26</A>
Acetaldehyde, In Ullmann’s Encyclopedia of Industrial Chemistry
7th ed.:
Wiley-VCH;
Weinheim:
2006.
<A NAME="RE17407SS-27">27</A>
Ishimure M.
Paradise in the Sea of Sorrow: Our Minamata Disease
Yamaguchi;
Kyoto:
1990.
<A NAME="RE17407SS-28A">28a</A>
Acetylene Chemistry
Diederich F.
Stang PJ.
Tykwinski RR.
Wiley-VCH;
Weinheim:
2005.
<A NAME="RE17407SS-28B">28b</A>
Modern Acetylene Chemistry
Diederich F.
Stang PJ.
Wiley-VCH;
Weinheim:
1995.
<A NAME="RE17407SS-29">29</A>
Desgrez A.
Ann. Chim.
1894,
3:
209
<A NAME="RE17407SS-30">30</A>
Kremsner JM.
Kappe CO.
Eur. J. Org. Chem.
2005,
3672
<A NAME="RE17407SS-31">31</A>
Vasudevan A.
Verzal MK.
Synlett
2004,
631
<A NAME="RE17407SS-32">32</A>
An G.
Bagnell L.
Cablewski T.
Strauss CR.
Trainor RW.
J. Org. Chem.
1997,
62:
2505
<A NAME="RE17407SS-33">33</A>
Olivi N.
Thomas E.
Peyrat J.
Alami M.
Brion J.
Synlett
2004,
2175
<A NAME="RE17407SS-34">34</A>
Le Bras G.
Provot L.
Peyrat J.
Alami M.
Brion J.
Tetrahedron Lett.
2006,
47:
5497
<A NAME="RE17407SS-35">35</A>
Chapdelaine MJ.
Warwick PJ.
Shaw A.
J. Org. Chem.
1989,
54:
1218
<A NAME="RE17407SS-36">36</A>
Tsuchimoto T.
Joya T.
Shirakawa E.
Kawakami Y.
Synlett
2000,
1777
<A NAME="RE17407SS-37A">37a</A>
Iimura S.
Manabe K.
Kobayashi S.
Org. Biomol. Chem.
2003,
1:
2416
<A NAME="RE17407SS-37B">37b</A>
Kupin BS.
Zh. Org. Khim.
1965,
1:
1206
<A NAME="RE17407SS-38">38</A>
Baeyer A.
Perkin WH.
Chem. Ber.
1883,
16:
2128
<A NAME="RE17407SS-39">39</A>
Pourzal A.
Bonnet P.
Monatsh. Chem.
1983,
114:
809
<A NAME="RE17407SS-40A">40a</A>
Meseguer B.
Alonso-Díaz D.
Griebenow N.
Herget T.
Waldmann H.
Angew. Chem. Int. Ed.
1999,
38:
2902
<A NAME="RE17407SS-40B">40b</A>
Duclos S.
Stoeckli-Evans H.
Ward TR.
Helv. Chim. Acta
2001,
84:
3148
<A NAME="RE17407SS-41A">41a</A>
Menashe N.
Reshef D.
Shvo Y.
J. Org. Chem.
1991,
56:
2912
<A NAME="RE17407SS-41B">41b</A>
Menashe N.
Shvo Y.
J. Org. Chem.
1993,
58:
7434
<A NAME="RE17407SS-42">42</A>
Xu G.
Hartman TL.
Wargo H.
Turpin JA.
Buckheit RW.
Cushman M.
Bioorg. Med. Chem.
2002,
10:
283
<A NAME="RE17407SS-43A">43a</A>
Chiang Y.
Kresge AJ.
Capponi M.
Wirz J.
Helv. Chim. Acta
1986,
69:
1331
<A NAME="RE17407SS-43B">43b</A>
Wan P.
Culshaw S.
Yates K.
J. Am. Chem. Soc.
1982,
104:
2509
<A NAME="RE17407SS-43C">43c</A>
Wooldridge T.
Roberts TD.
Tetrahedron Lett.
1973,
41:
4007
<A NAME="RE17407SS-44">44</A>
Schaad RE.
Ipatieff VN.
J. Am. Chem. Soc.
1940,
62:
178
<A NAME="RE17407SS-45A">45a</A>
Izumi Y.
Catal. Today
1997,
33:
371
<A NAME="RE17407SS-45B">45b</A>
Moggi P.
Albanesi G.
React. Kinet. Catal. Lett.
1991,
44:
375
<A NAME="RE17407SS-45C">45c</A>
Gorin YA.
Bogdanova LP.
Zh. Obshch. Khim.
1958,
28:
1144
<A NAME="RE17407SS-46">46</A>
Gut G.
Aufdereggen K.
Helv. Chim. Acta
1974,
57:
441
<A NAME="RE17407SS-47">47</A>
Moureu C.
Delange R.
C. R. Hebd. Seances Acad. Sci.
1903,
136:
753
<A NAME="RE17407SS-48A">48a</A>
Corey EJ.
Da Silva Jardine P.
Rohloff JC.
J. Am. Chem. Soc.
1988,
110:
3672
<A NAME="RE17407SS-48B">48b</A>
Corey EJ.
Cheng X.-M.
The Logic of Chemical Synthesis
John Wiley & Sons;
New York:
1989.
p.231
Esters:
<A NAME="RE17407SS-49A">49a</A>
Moureu C.
Lazennec I.
Bull. Soc. Chim. Fr.
1906,
1190
Nitriles:
<A NAME="RE17407SS-49B">49b</A>
Moureu C.
Lazennec I.
Bull. Soc. Chim. Fr.
1906,
1179
<A NAME="RE17407SS-49C">49c</A>
Moureu C.
Lazennec I.
Bull. Soc. Chim. Fr.
1907,
1062
Amides:
<A NAME="RE17407SS-49D">49d</A>
Moureu C.
Lazennec I.
Bull. Soc. Chim. Fr.
1907,
1066
For older applications, see ref. 9. Recent applications:
<A NAME="RE17407SS-50A">50a</A>
Chattha MS.
Aguiar AM.
J. Org. Chem.
1973,
38:
2908
<A NAME="RE17407SS-50B">50b</A>
Bestmann HJ.
Geismann C.
Zimmermann R.
Chem. Ber.
1994,
127:
1501
<A NAME="RE17407SS-50C">50c</A>
Abel S.
Faber D.
Hüter O.
Giese B.
Synthesis
1999,
188
<A NAME="RE17407SS-51">51</A>
Suzuki M.
Kambe M.
Tokuyama H.
Fukuyama T.
J. Org. Chem.
2004,
69:
2831
<A NAME="RE17407SS-52">52</A>
Kutscheroff MG.
Chem. Ber.
1909,
42:
2759
<A NAME="RE17407SS-53">53</A>
Budde WL.
Dessy RE.
J. Am. Chem. Soc.
1963,
85:
3964
<A NAME="RE17407SS-54">54</A>
Bassetti M.
Floris B.
Gazz. Chim. Ital.
1986,
116:
595
<A NAME="RE17407SS-55A">55a</A>
Bassetti M.
Floris B.
Illuminati G.
Organometallics
1985,
4:
617
<A NAME="RE17407SS-55B">55b</A>
Bassetti M.
Floris B.
J. Org. Chem.
1986,
51:
4140
<A NAME="RE17407SS-55C">55c</A>
Bassetti M.
Floris B.
J. Chem. Soc., Perkin Trans. 2
1988,
227
<A NAME="RE17407SS-56">56</A>
Nishizawa M.
Skwarczynski M.
Imagawa H.
Sugihara T.
Chem. Lett.
2002,
12
<A NAME="RE17407SS-57">57</A>
Stacy GW.
Mikulec RA.
Org. Synth. Coll. Vol. IV
1963,
13
<A NAME="RE17407SS-58">58</A>
Palomo C.
Oiarbide M.
Aizpurua JM.
Gonzàlez A.
Garcìa JM.
Landa C.
Odriozola I.
Linden A.
J. Org. Chem.
1999,
64:
8193
<A NAME="RE17407SS-59A">59a</A>
Paterson I.
Tudge M.
Tetrahedron
2003,
59:
6833
<A NAME="RE17407SS-59B">59b</A>
Paterson I.
Tudge M.
Angew. Chem. Int. Ed.
2003,
42:
343
<A NAME="RE17407SS-60">60</A>
Cox GG.
Moody CJ.
Austin DJ.
Padwa A.
Tetrahedron
1993,
49:
5109
<A NAME="RE17407SS-61A">61a</A>
Nieuwland JA.
Vogt RR.
Foohey WL.
J. Am. Chem. Soc.
1930,
52:
1018
<A NAME="RE17407SS-61B">61b</A>
Hennion GF.
Killian DB.
Vaughn TH.
Nieuwland JA.
J. Am. Chem. Soc.
1934,
56:
1130
<A NAME="RE17407SS-61C">61c</A>
Killian DB.
Hennion GF.
Nieuwland JA.
J. Am. Chem. Soc.
1934,
56:
1786
<A NAME="RE17407SS-61D">61d</A>
Killian DB.
Hennion GF.
Nieuwland JA.
J. Am. Chem. Soc.
1936,
58:
80
<A NAME="RE17407SS-62A">62a</A>
Islam AM.
Raphael RA.
J. Chem. Soc.
1952,
4086
<A NAME="RE17407SS-62B">62b</A>
Hamlet JC.
Henbest HB.
Jones ERH.
J. Chem. Soc.
1951,
2652
<A NAME="RE17407SS-62C">62c</A>
Monti H.
Bertrand M.
Tetrahedron
1973,
29:
2821
<A NAME="RE17407SS-63A">63a</A>
Newman MS.
J. Am. Chem. Soc.
1953,
75:
4740
<A NAME="RE17407SS-63B">63b</A>
Olah GA.
Meidar D.
Synthesis
1978,
671
<A NAME="RE17407SS-64">64</A>
Schick H.
Roatsch B.
Schramm S.
Gilsing H.
Ramm M.
Gründemann E.
J. Org. Chem.
1996,
61:
5788
<A NAME="RE17407SS-65">65</A>
Goldberg MW.
Aeschbacher R.
Helv. Chim. Acta
1939,
22:
1185
<A NAME="RE17407SS-66A">66a</A>
Goldberg MW.
Aeschbacher R.
Hardegger E.
Helv. Chim. Acta
1943,
26:
680
<A NAME="RE17407SS-66B">66b</A>
Montana AM.
Nicholas KM.
J. Org. Chem.
1990,
55:
1569
<A NAME="RE17407SS-67A">67a</A>
Stavely HE.
J. Am. Chem. Soc.
1942,
63:
3127
<A NAME="RE17407SS-67B">67b</A>
Goldberg MW.
Aeschbacher R.
Helv. Chim. Acta
1939,
22:
1188
<A NAME="RE17407SS-67C">67c</A>
Loritsch JA.
Vogt RR.
J. Am. Chem. Soc.
1939,
61:
1462
<A NAME="RE17407SS-68">68</A>
Janout V.
Regen SL.
J. Org. Chem.
1982,
47:
3331
<A NAME="RE17407SS-69">69</A>
Liu W.
Li J.
Chin. J. Org. Chem.
2006,
26:
1073
<A NAME="RE17407SS-70">70</A>
McDonald FE.
Chem. Eur. J.
1999,
5:
3103
<A NAME="RE17407SS-71A">71a</A>
Koo B.
McDonald FE.
Org. Lett.
2005,
7:
3621
<A NAME="RE17407SS-71B">71b</A>
McDonald FE.
Reddy KS.
Díaz Y.
J. Am. Chem. Soc.
2000,
122:
4304
<A NAME="RE17407SS-72">72</A>
Iwasawa N.
Shido M.
Kusama H.
J. Am. Chem. Soc.
2001,
123:
5814
<A NAME="RE17407SS-73">73</A>
Yadav J.
Das SK.
Sarkar S.
J. Am. Chem. Soc.
1997,
119:
4315
<A NAME="RE17407SS-74">74</A>
Damiano JP.
Postel M.
J. Organomet. Chem.
1996,
522:
303
<A NAME="RE17407SS-75">75</A>
Miranda PO.
Díaz DD.
Padrón JI.
Ramírez MA.
Martín VS.
J. Org. Chem.
2005,
70:
57
<A NAME="RE17407SS-76A">76a</A>
Halpern J.
James BR.
Kemp ALW.
J. Am. Chem. Soc.
1961,
83:
4097
<A NAME="RE17407SS-76B">76b</A>
Halpern J.
James BR.
Kemp ALW.
J. Am. Chem. Soc.
1966,
88:
5142
<A NAME="RE17407SS-77">77</A>
Taqui Khan MM.
Halligudi SB.
Shukla S.
J. Mol. Catal.
1990,
58:
299
<A NAME="RE17407SS-78">78</A>
Meier IK.
Marsella JA.
J. Mol. Catal.
1993,
78:
31
<A NAME="RE17407SS-79">79</A>
Bianchini C.
Casares JA.
Peruzzini M.
Romerosa A.
Zanobini F.
J. Am. Chem. Soc.
1996,
118:
4585
<A NAME="RE17407SS-80">80</A>
Tokunaga M.
Wakatsuki Y.
Angew. Chem. Int. Ed.
1998,
37:
2867
<A NAME="RE17407SS-81A">81a</A>
Hansen HD.
Nelson JH.
Organometallics
2000,
19:
4740
<A NAME="RE17407SS-81B">81b</A>
Ghebreyessus KY.
Nelson JH.
Inorg. Chim. Acta
2003,
350:
12
<A NAME="RE17407SS-82">82</A>
Cadierno V.
Crochet P.
García-Garrido SE.
Gimeno J.
Dalton Trans.
2004,
3635
<A NAME="RE17407SS-83">83</A>
Chen Y.
Valentini M.
Pregosin PS.
Albinati A.
Inorg. Chim. Acta
2002,
327:
4
<A NAME="RE17407SS-84">84</A>
Alvarez P.
Gimeno J.
Lastra E.
García-Granda S.
Van der Maelen JF.
Bassetti M.
Organometallics
2001,
20:
3762
<A NAME="RE17407SS-85">85</A>
Harman WD.
Dobson JC.
Taube H.
J. Am. Chem. Soc.
1989,
111:
3061
<A NAME="RE17407SS-86">86</A>
James BR.
Rempel GL.
J. Am. Chem. Soc.
1969,
91:
863
<A NAME="RE17407SS-87">87</A>
Blum J.
Huminer H.
Alper H.
J. Mol. Catal.
1992,
75:
153
<A NAME="RE17407SS-88">88</A>
Setty-Fichman M.
Sasson Y.
Blum J.
J. Mol. Catal.
1997,
126:
27
<A NAME="RE17407SS-89">89</A>
Chin CS.
Chang W.-T.
Yang S.
Joo K.-S.
Bull. Korean Chem. Soc.
1997,
18:
324
<A NAME="RE17407SS-90">90</A>
Hirabayashi T.
Okimoto Y.
Saito A.
Morita M.
Sakaguchi S.
Ishii Y.
Tetrahedron Lett.
2006,
62:
2231
<A NAME="RE17407SS-91">91</A>
Kim SY.
Chin CS.
Eum MS.
J. Mol. Catal.
2006,
253:
245
<A NAME="RE17407SS-92">92</A>
Ogo S.
Uehara K.
Abura T.
Watanabe Y.
Fukuzumi S.
J. Am. Chem. Soc.
2004,
126:
16520
<A NAME="RE17407SS-93A">93a</A>
Avshu A.
O’Sullivan RD.
Parkins AW.
Alcock NW.
Countryman RM.
J. Chem. Soc., Dalton Trans.
1983,
1619
<A NAME="RE17407SS-93B">93b</A>
Kataoka Y.
Matsumoto O.
Ohashi M.
Yamagata T.
Tani K.
Chem. Lett.
1994,
1283
<A NAME="RE17407SS-94">94</A>
Utimoto K.
Pure Appl. Chem.
1983,
55:
1845
<A NAME="RE17407SS-95">95</A>
Liu B.
De Brabander JK.
Org. Lett.
2006,
8:
4907
<A NAME="RE17407SS-96">96</A>
Imi K.
Imai K.
Utimoto K.
Tetrahedron Lett.
1987,
28:
3127
<A NAME="RE17407SS-97">97</A>
Fukuda Y.
Shiragami H.
Utimoto K.
Nozaki H.
J. Org. Chem.
1991,
56:
5816
<A NAME="RE17407SS-98">98</A>
Arcadi A.
Cacchi S.
Marinelli F.
Tetrahedron
1993,
49:
4955
<A NAME="RE17407SS-99">99</A>
Sokol’skii DV,
Dorfman YaA, and
Segizbaeva SS. inventors; S.U. Patent 398270.
; Chem. Abstr. 1974, 81, 49251
<A NAME="RE17407SS-100">100</A>
Chatt J.
Guy RG.
Duncanson LA.
J. Chem. Soc.
1961,
827
<A NAME="RE17407SS-101">101</A>
Hiscox W.
Jennings PW.
Organometallics
1990,
9:
1997
<A NAME="RE17407SS-102">102</A>
Hartman JW.
Hiscox WC.
Jennings PW.
J. Org. Chem.
1993,
58:
7613
<A NAME="RE17407SS-103">103</A>
Jennings PW.
Hartman JW.
Hiscox WC.
Inorg. Chim. Acta
1994,
222:
317
<A NAME="RE17407SS-104">104</A>
Hartman JW.
Sperry L.
Tetrahedron Lett.
2004,
45:
3787
<A NAME="RE17407SS-105">105</A>
Badrieh Y.
Kayyal A.
Blum J.
J. Mol. Catal.
1992,
75:
161
<A NAME="RE17407SS-106A">106a</A>
Baidossi W.
Lahav M.
Blum J.
J. Org. Chem.
1997,
62:
669
<A NAME="RE17407SS-106B">106b</A>
Israelsohn O.
Vollhardt KPC.
Blum J.
J. Mol. Catal.
2002,
184:
1
<A NAME="RE17407SS-107">107</A>
Francisco LW.
Moreno DA.
Atwood JD.
Organometallics
2001,
20:
4237
<A NAME="RE17407SS-108">108</A>
Lucey DW.
Atwood JD.
Organometallics
2002,
21:
2481
<A NAME="RE17407SS-109">109</A>
Vartanyan SA.
Pirenyan SK.
Manasyan NG.
Zh. Obshch. Khim.
1961,
31:
2436
<A NAME="RE17407SS-110">110</A>
Shestakov GK.
Vsesvyatskaya NY.
Stepanov AM.
Temkin ON.
Kinet. Catal.
1976,
17:
815
<A NAME="RE17407SS-111">111</A>
Shestakov GK.
Temkin ON.
Vsesvyatskaya NY.
Stepanov AM.
Zh. Org. Khim.
1979,
15:
248
<A NAME="RE17407SS-112A">112a</A>
Vsesvyatskaya NY.
Shestakov GK.
Temkin ON.
Kinet. Catal.
1986,
27:
1330
<A NAME="RE17407SS-112B">112b</A>
Vsesvyatskaya NY.
Tsyganov DV.
Bykov AM.
Shestakov GK.
Temkin ON.
Zh. Org. Khim.
1985,
21:
2041
<A NAME="RE17407SS-113">113</A>
Vsesvyatskaya NY.
Shestakov GK.
Temkin ON.
Kinet. Catal.
1988,
29:
965
<A NAME="RE17407SS-114">114</A>
Sokol’skii DV.
Dorfman YA.
Karazhanova NA.
Nogerbekov BY.
Zh. Org. Khim.
1971,
7:
1581
<A NAME="RE17407SS-115">115</A>
Tokita Y.
Okamoto A.
Nishiwaki K.
Kobayashi M.
Nakamura E.
Bull. Chem. Soc. Jpn.
2004,
77:
1395
<A NAME="RE17407SS-116">116</A>
Easton NR.
Cassady DR.
Dillard RD.
J. Org. Chem.
1965,
30:
3084
<A NAME="RE17407SS-117">117</A>
Pale P.
Chuche J.
Eur. J. Org. Chem.
2000,
1019
<A NAME="RE17407SS-118">118</A>
Kataoka Y.
Matsumoto O.
Tani K.
Chem. Lett.
1996,
727
<A NAME="RE17407SS-119">119</A>
Norman ROC.
Parr WJE.
Thomas CB.
J. Chem. Soc., Perkin Trans. 1
1976,
1983
<A NAME="RE17407SS-120">120</A>
Fukuda Y.
Utimoto K.
J. Org. Chem.
1991,
56:
3729
<A NAME="RE17407SS-121">121</A>
Fukuda Y.
Utimoto K.
Bull. Chem. Soc. Jpn.
1991,
64:
2013
<A NAME="RE17407SS-122">122</A>
Casado R.
Contel M.
Laguna M.
Romero P.
Sanz S.
J. Am. Chem. Soc.
2003,
125:
11925
<A NAME="RE17407SS-123A">123a</A>
Teles S.
Brode S.
Chabanas M.
Angew. Chem. Int. Ed.
1998,
37:
1415
<A NAME="RE17407SS-123B">123b</A>
Schulz M, and
Teles JH. inventors; U.S. Patent 6037482.
; Chem. Abstr. 1997, 127, 121499
<A NAME="RE17407SS-124">124</A>
Dyker G.
Angew. Chem. Int. Ed.
2000,
39:
4327
<A NAME="RE17407SS-125">125</A>
Mizushima E.
Sato K.
Hayashi T.
Tanaka M.
Angew. Chem. Int. Ed.
2002,
41:
4563
<A NAME="RE17407SS-126">126</A>
Mizushima E.
Cui D.
Nath DCD.
Hayashi T.
Tanaka M.
Org. Synth.
2006,
83:
55
<A NAME="RE17407SS-127">127</A>
Roembke P.
Schmidbaur H.
Cronje S.
Raubenheimer H.
J. Mol. Catal.
2004,
212:
35
<A NAME="RE17407SS-128">128</A>
Schneider SK.
Herrmann WA.
Herdtweck E.
Z. Anorg. Allg. Chem.
2003,
629:
2363
<A NAME="RE17407SS-129">129</A>
Zhou C.
Chan PWH.
Che C.
Org. Lett.
2006,
8:
325
<A NAME="RE17407SS-130">130</A>
Ban M, and
Ida F. inventors; U.S. Patent 2791614.
; Chem. Abstr. 1957, 51, 85804
<A NAME="RE17407SS-131">131</A>
Hu NX.
Aso Y.
Otsubo T.
Ogura F.
Tetrahedron Lett.
1986,
27:
6099
<A NAME="RE17407SS-132">132</A>
Uemura S.
Kitoh R.
Fujita K.
Ichikawa K.
Bull. Chem. Soc. Jpn.
1967,
40:
1499
<A NAME="RE17407SS-133">133</A>
Uemura S.
Miyoshi H.
Okano M.
Ichikawa K.
J. Chem. Soc., Perkin Trans. 1
1981,
991
<A NAME="RE17407SS-134">134</A>
Sasaki Y.
Dixneuf PH.
J. Chem. Soc., Chem. Commun.
1986,
790
<A NAME="RE17407SS-135">135</A>
Mahé R.
Dixneuf PH.
Lécolier S.
Tetrahedron Lett.
1986,
27:
6333
<A NAME="RE17407SS-136">136</A>
Bruneau C.
Dixneuf PH.
Angew. Chem. Int. Ed.
2006,
45:
2176
<A NAME="RE17407SS-137">137</A>
See section 3.3.5 for a Cu-catalyst that generates considerable amounts of anti-Markovnikov
product.
<A NAME="RE17407SS-138">138</A>
Tokunaga M, and
Wakatsuki Y. inventors; Jap. Patent 11319576 A2.
; Chem. Abstr. 1999, 131, 352828
<A NAME="RE17407SS-139">139</A>
Suzuki T.
Tokunaga M.
Wakatsuki Y.
Org. Lett.
2001,
3:
735
<A NAME="RE17407SS-140">140</A>
Suzuki T,
Wakatsuki Y, and
Tokunaga M. inventors; Jap. Patent 2002114730 A2.
; Chem. Abstr. 2002, 136, 309681
<A NAME="RE17407SS-141">141</A>
dppe = 1,2-bis(diphenylphosphino)ethane; dppb = 1,4-bis(diphenylphosphino)butane.
<A NAME="RE17407SS-142">142</A>
Py-BOX-
i
Pr = 2,6-bis(4-(isopropyl)-2-oxazolin-2-yl)pyridine.
<A NAME="RE17407SS-143">143</A>
Grotjahn DB.
Incarvito CD.
Rheingold AL.
Angew. Chem. Int. Ed.
2001,
40:
3884
<A NAME="RE17407SS-144">144</A>
Grotjahn DB.
Lev DA.
J. Am. Chem. Soc.
2004,
126:
12232
<A NAME="RE17407SS-145">145</A>
Chevallier F.
Breit B.
Angew. Chem. Int. Ed.
2006,
45:
1599
<A NAME="RE17407SS-146">146</A>
Baur J.
Jacobsen H.
Burger P.
Artus G.
Berke H.
Dahlenburg L.
Eur. J. Inorg. Chem.
2000,
1411
<A NAME="RE17407SS-147">147</A>
Note that Grotjahn’s complex D is available in research quantities from Strem Chemicals.
<A NAME="RE17407SS-148">148</A>
Kündig EP.
Monnier FR.
Adv. Synth. Catal.
2004,
346:
901
<A NAME="RE17407SS-149">149</A>
Labonne A.
Kribber T.
Hintermann L.
Org. Lett.
2006,
8:
5853
<A NAME="RE17407SS-150">150</A>
Hintermann, L.; Labonne, A.; Kribber, T.; Paciok, E. unpublished results.
<A NAME="RE17407SS-151">151</A>
Alvarez P.
Bassetti M.
Gimeno J.
Mancini G.
Tetrahedron Lett.
2001,
42:
8467
<A NAME="RE17407SS-152">152</A>
Suzuki T.
Tokunaga M.
Wakatsuki Y.
Tetrahedron Lett.
2002,
43:
7531
<A NAME="RE17407SS-153">153</A>
d’Alessandro N.
Di Deo M.
Bonetti M.
Tonucci L.
Morvillo A.
Bressan M.
Eur. J. Inorg. Chem.
2004,
810
<A NAME="RE17407SS-154">154</A>
Kribber, T.; Labonne, A.; Hintermann, L. manuscript submitted.
<A NAME="RE17407SS-155">155</A>
Bolm, C.; Labonne, A.; Zani, L.; Hintermann, L. manuscript in preparation.
<A NAME="RE17407SS-156">156</A>
Rosner BM.
Schink B.
J. Bacteriol.
1995,
177:
5767
<A NAME="RE17407SS-157">157</A>
Meckenstock RU.
Krieger R.
Ensign S.
Kroneck PMH.
Schink B.
Eur. J. Biochem.
1999,
264:
176
<A NAME="RE17407SS-158">158</A>
Boll M.
Schink B.
Messerschmidt A.
Kroneck PMH.
Biol. Chem.
2005,
386:
999
<A NAME="RE17407SS-159">159</A>
Yamada EW.
Jakoby WB.
J. Am. Chem. Soc.
1958,
80:
2343
<A NAME="RE17407SS-160">160</A>
Yamada EW.
Jakoby WB.
J. Biol. Chem.
1959,
234:
941
<A NAME="RE17407SS-161">161</A>
Thorpe C.
Anal. Biochem.
1986,
155:
391
<A NAME="RE17407SS-162">162</A>
Alipui OD.
Zhang D.
Schulz H.
Biochem. Biophys. Res. Commun.
2002,
292:
1171
<A NAME="RE17407SS-163">163</A>
Wang SC.
Person MD.
Johnson WH.
Whitman CP.
Biochemistry
2003,
42:
8762
<A NAME="RE17407SS-164">164</A>
Schmid GH. In
Chemistry of the Carbon-Carbon Triple Bond
Patai S.
John Wiley;
Chichester:
1978.
p.275
<A NAME="RE17407SS-165A">165a</A>
Allen AD.
Chiang Y.
Kresge JA.
Tidwell TT.
J. Org. Chem.
1982,
47:
775
<A NAME="RE17407SS-165B">165b</A>
Noyce DS.
Schiavelli MD.
J. Am. Chem. Soc.
1968,
90:
1020
<A NAME="RE17407SS-165C">165c</A>
Noyce DS.
Matesich MA.
Peterson PE.
J. Am. Chem. Soc.
1967,
89:
6225
<A NAME="RE17407SS-166">166</A>
Lucchini V.
Modenan G.
J. Am. Chem. Soc.
1990,
112:
6291
<A NAME="RE17407SS-167">167</A>
Barluenga J.
Aznar F.
Liz R.
Rodes R.
J. Chem. Soc., Perkin Trans. 1
1983,
1087
<A NAME="RE17407SS-168A">168a</A>
Uemura S.
Miyoshi H.
Okano M.
J. Chem. Soc., Perkin Trans. 1
1980,
1098
<A NAME="RE17407SS-168B">168b</A>
Bach RD.
Woodard RA.
Anderson TJ.
Glick MD.
J. Org. Chem.
1982,
47:
3707
<A NAME="RE17407SS-168C">168c</A>
Bassetti MP.
Bocelli TG.
Organometallics
1990,
9:
2292
<A NAME="RE17407SS-169">169</A>
Rekasheva AF.
Samchenko IP.
Dokl. Akad. Nauk SSSR
1960,
133:
1340
<A NAME="RE17407SS-170">170</A>
Paquette LA.
Bolin DG.
Stepanian M.
Branan BM.
Mallavadhani UV.
Tae J.
Eisenberg SWE.
Rogers RD.
J. Am. Chem. Soc.
1998,
120:
11603
<A NAME="RE17407SS-171">171</A>
Diedenhofen M.
Ph.D. Dissertation
University of Marburg;
Germany:
2000.
<A NAME="RE17407SS-172">172</A>
Tokunaga M.
Suzuki T.
Koga N.
Fukushima T.
Horiuchi A.
Wakatsuki Y.
J. Am. Chem. Soc.
2001,
123:
11917
<A NAME="RE17407SS-173">173</A>
Grotjahn DB.
Chem. Eur. J.
2005,
11:
7146
<A NAME="RE17407SS-174">174</A>
Jalón FA.
Manzano BR.
Caballero A.
Carrión MC.
Santos L.
Espino G.
Moreno M.
J. Am. Chem. Soc.
2005,
127:
15364
<A NAME="RE17407SS-175">175</A>
Vo-Quang L.
Cadiot P.
Bull. Soc. Chim. Fr.
1965,
1518
<A NAME="RE17407SS-176">176</A>
Liese T.
de Meijere A.
Chem. Ber.
1986,
119:
2995
<A NAME="RE17407SS-177">177</A>
Siegel H.
Eisenhuth L.
Hopf H.
Chem. Ber.
1985,
118:
597
<A NAME="RE17407SS-178">178</A>
Kieczykowszi GR.
Quesada Martha L.
Schlessinger RH.
J. Am. Chem. Soc.
1980,
102:
782
<A NAME="RE17407SS-179">179</A>
Ley SV.
Brown DS.
Clase JA.
Fairbanks AJ.
Lennon IC.
Osborn HMI.
Stokes ESE.
Wadsworth DJ.
J. Chem. Soc., Perkin Trans. 1
1998,
2259
<A NAME="RE17407SS-180">180</A>
Conawa RF. inventors; U.S. Patent 1967225.
; Chem. Abstr. 1934, 28, 48111
<A NAME="RE17407SS-181">181</A>
McMahon EM.
Roper JN.
Untermohlen WP.
Hasek RH.
Harris RC.
Brant JH.
J. Am. Chem. Soc.
1948,
70:
2976
<A NAME="RE17407SS-182">182</A>
Nazarov IN.
Vartanyan SA.
Matsoyan SG.
Zhamagortsyan VN.
Zh. Obshch. Khim.
1953,
23:
1986
<A NAME="RE17407SS-183">183</A>
Treibs A.
Angew. Chem.
1948,
60:
289
<A NAME="RE17407SS-184">184</A>
Jung ME.
Nishimura N.
Org. Lett.
2001,
3:
2113
<A NAME="RE17407SS-185">185</A>
Ohyabu N.
Nishikawa T.
Isobe M.
J. Am. Chem. Soc.
2003,
125:
8798
<A NAME="RE17407SS-186">186</A>
Kabbe H.-J.
Truscheit E.
Eiter K.
Liebigs Ann. Chem.
1965,
684:
14
<A NAME="RE17407SS-187">187</A>
Skinnemoen K.
Undheim K.
Acta Chem. Scand., Ser. B
1980,
34:
295
<A NAME="RE17407SS-188">188</A>
Campbell ID.
Dobson NA.
Eglinton G.
J. Chem. Soc.
1964,
1092
<A NAME="RE17407SS-189">189</A>
Burgess C.
Burn D.
Feather P.
Howarth M.
Petrow V.
Tetrahedron
1965,
21:
1197
<A NAME="RE17407SS-190">190</A>
Zanina AS.
Shergina SI.
Khabibulina GN.
Sokolov IE.
Kirchanov AA.
Myasnikova RN.
Kotlyarevskii IL.
Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.)
1977,
26:
2572
<A NAME="RE17407SS-191">191</A>
Krüger K.
Gössl T.
Angew. Chem.
1953,
65:
558
<A NAME="RE17407SS-192A">192a</A>
Seebach D.
Angew. Chem., Int. Ed. Engl.
1979,
18:
239
<A NAME="RE17407SS-192B">192b</A>
Warren S.
Organic Synthesis - The Disconnection Approach
John Wiley & Sons;
Chichester:
1982.
p.126 and 185
<A NAME="RE17407SS-192C">192c</A>
Lever OW.
Tetrahedron
1976,
32:
1943
<A NAME="RE17407SS-193">193</A>
Somers PK.
Wandless TJ.
Schreiber SL.
J. Am. Chem. Soc.
1991,
113:
8045
<A NAME="RE17407SS-194">194</A>
Fernandez-Megia E.
Gourlaouen N.
Ley SV.
Rowlands GJ.
Synlett
1998,
991
<A NAME="RE17407SS-195">195</A>
Sayo N.
Nakai E.-I.
Nakai T.
Chem. Lett.
1985,
1723
<A NAME="RE17407SS-196">196</A>
Swaminathan S.
Narayanan KV.
Chem. Rev.
1971,
71:
429
<A NAME="RE17407SS-197">197</A>
Lorber CY.
Osborn JA.
Tetrahedron Lett.
1996,
37:
853
<A NAME="RE17407SS-198">198</A>
Jirkovski I.
Cayen MN.
J. Med. Chem.
1982,
25:
1154
<A NAME="RE17407SS-199">199</A>
Palomo C.
González A.
García JM.
Landa C.
Oiarbide M.
Rodríguez S.
Linden A.
Angew. Chem. Int. Ed.
1998,
37:
180
<A NAME="RE17407SS-200A">200a</A>
Shoppee CW.
Prins DA.
Helv. Chim. Acta
1943,
26:
201
<A NAME="RE17407SS-200B">200b</A>
Ruzicka L.
Gätzi K.
Reichstein T.
Helv. Chim. Acta
1939,
22:
626
<A NAME="RE17407SS-201">201</A>
Kende AS.
Tsay Y.
Mills JE.
J. Am. Chem. Soc.
1976,
98:
1967
<A NAME="RE17407SS-202">202</A>
Krohn K.
Ostermeyer H.-H.
Tolkiehn K.
Chem. Ber.
1979,
112:
2640
<A NAME="RE17407SS-203">203</A>
Bourghli LMS.
Stoodley RJ.
Bioorg. Med. Chem.
2004,
12:
2863
<A NAME="RE17407SS-204">204</A>
Ikeda N.
Omori K.
Yamamoto H.
Tetrahedron Lett.
1986,
27:
1175
<A NAME="RE17407SS-205">205</A>
Gilly C.
Taillandier G.
Pera MH.
Luu-Duc C.
Demenge P.
de Catanho MT.
Eur. J. Med. Chem.
1997,
32:
365
<A NAME="RE17407SS-206">206</A>
Karrer F. inventors; U.S. Patent 4172146.
; Chem. Abstr. 1980, 92, 94080
<A NAME="RE17407SS-207">207</A>
Leder J.
Fujioka H.
Kishi Y.
Tetrahedron Lett.
1983,
24:
1463
<A NAME="RE17407SS-208">208</A>
Jung HH.
Floreancig PE.
Org. Lett.
2006,
8:
1949
<A NAME="RE17407SS-209">209</A>
Turuta AM.
Fadeeva TM.
Kamernitskii AV.
Khim. Farm. Zh.
1992,
26:
84
<A NAME="RE17407SS-210">210</A>
Panchenko YV.
Petrovskaya GA.
Kushnir LV.
Puchin VA.
J. Org. Chem. USSR (Engl. Transl.)
1987,
23:
1640
<A NAME="RE17407SS-211">211</A>
Stevens RV.
Cherpeck RE.
Harrison BL.
Lai J.
Lapalme R.
J. Am. Chem. Soc.
1976,
98:
6317
<A NAME="RE17407SS-212A">212a</A>
Takeda K.
Shimono Y.
Yoshii E.
J. Am. Chem. Soc.
1983,
105:
563
<A NAME="RE17407SS-212B">212b</A>
Brown E.
Ragault M.
Touet J.
Bull. Soc. Chim. Fr.
1971,
2195
<A NAME="RE17407SS-212C">212c</A>
Nakasuji K.
Todo E.
Murta I.
Angew. Chem., Int. Ed. Engl.
1977,
16:
784
<A NAME="RE17407SS-213A">213a</A>
Hooz J.
Layton RB.
J. Am. Chem. Soc.
1971,
93:
7320
<A NAME="RE17407SS-213B">213b</A>
Saha M.
Bagby B.
Nicholas KM.
Tetrahedron Lett.
1986,
27:
915
<A NAME="RE17407SS-214">214</A>
Dauben WG.
McFarland JW.
Rogan JB.
J. Org. Chem.
1961,
26:
297
<A NAME="RE17407SS-215">215</A>
Baek D.-J.
Daniels SB.
Reed PE.
Katzenellenbogen JA.
J. Org. Chem.
1989,
54:
3963
<A NAME="RE17407SS-216">216</A>
Jacobi PA.
Herradura P.
Tetrahedron Lett.
1997,
38:
6621
<A NAME="RE17407SS-217A">217a</A>
Crout DHG.
Hassall CH.
Jones TL.
J. Chem. Soc.
1964,
2187
<A NAME="RE17407SS-217B">217b</A>
Bowden K.
Braude EA.
Jones ERH.
J. Chem. Soc.
1946,
945
<A NAME="RE17407SS-218A">218a</A>
Sakamoto T.
Kondo Y.
Shiraiwa M.
Yamanaka H.
Synthesis
1984,
245
<A NAME="RE17407SS-218B">218b</A>
Tanji K.
Sakamoto T.
Yamanaka H.
Chem. Pharm. Bull.
1982,
30:
1865
<A NAME="RE17407SS-219">219</A>
Reppe W, and
Ritzenthaler B. inventors; DE Patent 897565.
; Chem. Abstr. 1958, 52, 92727
<A NAME="RE17407SS-220">220</A>
Botbaeva KA.
Praliev KD.
Poplavskaya IA.
Nauyryzova BZ.
Russ. J. Org. Chem. (Engl. Transl.)
2000,
36:
1509
<A NAME="RE17407SS-221A">221a</A>
Hennion GF.
Butler PE.
J. Org. Chem.
1961,
26:
3341
<A NAME="RE17407SS-221B">221b</A>
Wolf V.
Liebigs Ann. Chem.
1952,
578:
83
<A NAME="RE17407SS-222">222</A>
Shmidt EY.
Vasiltsov AM.
Mikhaleva AI.
Zaitsev AB.
Arndt J.
Henkelmann J.
Trofimov BA.
Russ. J. Org. Chem. (Engl. Transl.)
2002,
38:
1808
<A NAME="RE17407SS-223">223</A>
Eloy F.
Deryckere A.
Chim. Ther.
1973,
8:
437
<A NAME="RE17407SS-224">224</A>
Golodova KG.
Yakimovich SI.
J. Org. Chem. USSR (Engl. Transl.)
1972,
8:
2062
<A NAME="RE17407SS-225">225</A>
Haruta J.
Nishi K.
Matsuda S.
Akai S.
Tamura Y.
Kita Y.
J. Org. Chem.
1990,
55:
4853
<A NAME="RE17407SS-226">226</A>
Farina F.
Noheda P.
Paredes MC.
Tetrahedron Lett.
1991,
32:
1109
<A NAME="RE17407SS-227">227</A>
Alker D.
Campbell SF.
Cross PE.
J. Med. Chem.
1991,
34:
19
<A NAME="RE17407SS-228">228</A>
Witulski B.
Bergstraesser U.
Goessmann M.
Tetrahedron
2000,
56:
4747
<A NAME="RE17407SS-229">229</A>
Stacy GW.
Barnett BF.
Strong PL.
J. Org. Chem.
1965,
30:
592
<A NAME="RE17407SS-230">230</A>
Spry DO.
Tetrahedron Lett.
1980,
21:
1293
<A NAME="RE17407SS-231">231</A>
Barre V.
Massias F.
Uguen D.
Tetrahedron Lett.
1989,
30:
7389
<A NAME="RE17407SS-232A">232a</A>
Haszeldine RN.
Leedham K.
J. Chem. Soc.
1952,
3483
<A NAME="RE17407SS-232B">232b</A>
Henne AL.
Nager M.
J. Am. Chem. Soc.
1952,
74:
650
<A NAME="RE17407SS-233">233</A>
Talybov GM.
Nurieva UG.
Karaev SF.
Russ. J. Org. Chem. (Engl. Transl.)
2003,
39:
1206
<A NAME="RE17407SS-234">234</A>
Ando T.
Shioi S.
Nakagawa M.
Bull. Chem. Soc. Jpn.
1972,
45:
2611
<A NAME="RE17407SS-235">235</A>
Nozaki H.
Kato S.
Noyori R.
Can. J. Chem.
1966,
44:
1021
<A NAME="RE17407SS-236">236</A>
Petrov AA.
Kupin BS.
Zh. Obshch. Khim.
1959,
29:
3153
<A NAME="RE17407SS-237">237</A>
Detert H.
Meier H.
Liebigs Ann./Recl.
1997,
1565
<A NAME="RE17407SS-238A">238a</A>
Kupin BS.
Petrov AA.
J. Gen. Chem. USSR (Engl. Transl.)
1963,
33:
3799
<A NAME="RE17407SS-238B">238b</A>
Colonge J.
Varagnat A.
Bull. Soc. Chim. Fr.
1964,
561
<A NAME="RE17407SS-239">239</A>
Gensler WJ.
Petitipierre J.-C.
Dean JW.
J. Org. Chem.
1978,
43:
4081
<A NAME="RE17407SS-240">240</A>
Bohlmann F.
Viehe H.-G.
Chem. Ber.
1955,
88:
1017
<A NAME="RE17407SS-241">241</A>
Constantino MG.
Donate PM.
Petragnani N.
Tetrahedron Lett.
1982,
23:
1051
<A NAME="RE17407SS-242A">242a</A>
Nazarov IN.
Zaretskaya II.
Izv. Akad. Nauk SSSR Ser. Khim.
1941,
211
<A NAME="RE17407SS-242B">242b</A>
Nazarov IN.
Zaretskaya II.
Izv. Akad. Nauk SSSR Ser. Khim.
1946,
529
<A NAME="RE17407SS-243">243</A>
Nazarov IN.
Burmistrova MS.
Zh. Obshch. Khim.
1950,
20:
1304
<A NAME="RE17407SS-244A">244a</A>
Tius MA.
Eur. J. Org. Chem.
2005,
2193
<A NAME="RE17407SS-244B">244b</A>
Habermas KL.
Denmark SE.
Jones TK.
Org. React.
1994,
45:
1
<A NAME="RE17407SS-245">245</A>
Kovalev BG.
Sorochinskaya AM.
Avdeeva LA.
Chem. Nat. Compd. (USSR)
1988,
24:
110
<A NAME="RE17407SS-246">246</A>
Pal M.
Parasuraman K.
Gupta S.
Yeleswarapu KR.
Synlett
2002,
1976
<A NAME="RE17407SS-247">247</A>
Kaptein B.
Barf G.
Kellogg RM.
Van Bolhuis F.
J. Org. Chem.
1990,
55:
1890
<A NAME="RE17407SS-248">248</A>
Hennion GF.
Kupiecki FP.
J. Org. Chem.
1953,
18:
1601
<A NAME="RE17407SS-249">249</A>
Cappi MW.
Moree WJ.
Qiao L.
Marron TG.
Weitz-Schmidt G.
Wong C.-H.
Bioorg. Med. Chem.
1997,
5:
283
<A NAME="RE17407SS-250">250</A>
Dupont G.
Ann. Chim.
1913,
30:
485-535
<A NAME="RE17407SS-251">251</A>
Newman MS.
Reichle WR.
Org. Synth. Coll. Vol. V
1973,
1024
<A NAME="RE17407SS-252">252</A>
Saimoto H.
Hiyama T.
Nozaki H.
Bull. Chem. Soc. Jpn.
1983,
56:
3078
<A NAME="RE17407SS-253">253</A>
Froning JF.
Hennion GF.
J. Am. Chem. Soc.
1940,
62:
653
<A NAME="RE17407SS-254A">254a</A>
Stork G.
Borch R.
J. Am. Chem. Soc.
1964,
86:
935
<A NAME="RE17407SS-254B">254b</A>
Stork G.
Borch R.
J. Am. Chem. Soc.
1964,
86:
936
<A NAME="RE17407SS-255">255</A>
Ruggli P.
Staub A.
Helv. Chim. Acta
1936,
19:
962
<A NAME="RE17407SS-256">256</A>
Thomas AF.
Damm H.
Tetrahedron Lett.
1986,
27:
505
<A NAME="RE17407SS-257">257</A>
Poss AJ.
Belter RK.
J. Org. Chem.
1987,
52:
4810
<A NAME="RE17407SS-258">258</A>
Liu Y.
Liu M.
Guo S.
Tu H.
Zhou Y.
Gao H.
Org. Lett.
2006,
8:
3445
<A NAME="RE17407SS-259">259</A>
Rajaram AR.
Pu L.
Org. Lett.
2006,
8:
2019
<A NAME="RE17407SS-260">260</A>
Trost BM.
Toste FD.
Greenman K.
J. Am. Chem. Soc.
2003,
125:
4518
<A NAME="RE17407SS-261">261</A>
Gomez V.
Perez-Medrano A.
Muchowski JM.
J. Org. Chem.
1994,
59:
1219
<A NAME="RE17407SS-262">262</A>
Koulkes M.
C. R. Hebd. Seances Acad. Sci.
1955,
241:
1789
<A NAME="RE17407SS-263">263</A>
Scarpa JS.
Ribi M.
Eugster CH.
Helv. Chim. Acta
1966,
49:
858
<A NAME="RE17407SS-264">264</A>
Douglas GH.
Graves JMH.
Hartley D.
Hughes GA.
McLoughlin BJ.
Siddall J.
Smith H.
J. Chem. Soc.
1963,
5072
<A NAME="RE17407SS-265">265</A>
Reed MW.
Moore HW.
J. Org. Chem.
1988,
53:
4166
<A NAME="RE17407SS-266">266</A>
Arcadi A.
Rossi E.
Tetrahedron
1998,
54:
15253
<A NAME="RE17407SS-267A">267a</A>
Yamanaka H.
Shiraiwa M.
Sakamoto T.
Konno S.
Chem. Pharm. Bull.
1981,
29:
3548
<A NAME="RE17407SS-267B">267b</A>
Konno S.
Shiraiwa M.
Yamanaka H.
Chem. Pharm. Bull.
1981,
29:
3554
<A NAME="RE17407SS-268">268</A>
Arcadi A.
Cacchi S.
Fabrizi G.
Marinelli F.
Parisi LM.
J. Org. Chem.
2005,
70:
6213
<A NAME="RE17407SS-269">269</A>
Robins MJ.
Barr PJ.
J. Org. Chem.
1983,
48:
1854
<A NAME="RE17407SS-270">270</A>
Acevedo OL.
Andrews RS.
Dunkel M.
Cook PD.
J. Heterocycl. Chem.
1994,
31:
989
<A NAME="RE17407SS-271A">271a</A>
Trost BM.
Frederiksen MU.
Rudd MT.
Angew. Chem. Int. Ed.
2005,
44:
6630
<A NAME="RE17407SS-271B">271b</A>
Trost BM.
Acc. Chem. Res.
2002,
35:
695
<A NAME="RE17407SS-272">272</A>
Park YJ.
Kwon B.-I.
Ahn J.-A.
Lee H.
Jun C.-H.
J. Am. Chem. Soc.
2004,
126:
13892
<A NAME="RE17407SS-273A">273a</A>
Trost BM.
Portnoy M.
Kurihara H.
J. Am. Chem. Soc.
1997,
119:
836
<A NAME="RE17407SS-273B">273b</A>
Trost BM.
Rudd MT.
J. Am. Chem. Soc.
2003,
125:
11916
<A NAME="RE17407SS-273C">273c</A>
Chen Y.
Ho DM.
Lee C.
J. Am. Chem. Soc.
2005,
127:
12184
<A NAME="RE17407SS-273D">273d</A>
Odedra A.
Wu C.-J.
Pratap TB.
Huang C.-W.
Ran Y.-F.
Liu R.-S.
J. Am. Chem. Soc.
1995,
127:
3406
<A NAME="RE17407SS-274">274</A>
The price of 1 g of AuMe(PPh3) corresponds to that of 1 kg of mercury(II) sulfate!
