Abstract
Zwitterionic iodonium compounds, ZICs, a major class of hypervalent
iodine compounds, are flexible units that offer access to interesting
structures. This Account focuses on the synthetic applications of
iodonium phenolates, ylides of hydroxycoumarins and, mainly, ylides
of hydroxyquinones.
1 Background
2 Iodonium Phenolates
3 Ylides of Hydroxycoumarins
4 Ylides of Hydroxyquinones
5 Summary and Perspectives
Key words
iodonium - zwitterions - ylides - hydroxyquinones - synthesis
References
<A NAME="RA49108ST-1A">1a</A>
Varvoglis A.
Hypervalent
Iodine in Organic Synthesis
Academic Press;
London:
1997.
<A NAME="RA49108ST-1B">1b</A>
Hypervalent
Iodine Chemistry
Wirth T.
Springer-Verlag;
Berlin:
2003.
<A NAME="RA49108ST-1C">1c</A>
Koser GF.
Aldrichimica Acta
2001,
34:
89
<A NAME="RA49108ST-1D">1d</A>
Togo H.
Katoghi M.
Synlett
2001,
566
<A NAME="RA49108ST-1E">1e</A>
Togo H.
Sakurani M.
Synlett
2002,
1966
<A NAME="RA49108ST-1F">1f</A>
Zhdankin VV.
Stang PJ.
Chem.
Rev.
2002,
102:
2523
<A NAME="RA49108ST-1G">1g</A>
Dauban P.
Dodd RH.
Synlett
2003,
11
<A NAME="RA49108ST-1H">1h</A>
Stang PJ.
J. Org. Chem.
2003,
68:
2997
<A NAME="RA49108ST-1I">1i</A>
Tohma H.
Kita Y.
Adv. Synth. Catal.
2004,
346:
111
<A NAME="RA49108ST-1J">1j</A>
Koser GF.
Adv. Heterocycl. Chem.
2004,
86:
225
<A NAME="RA49108ST-1K">1k</A>
Moriarty RM.
J. Org. Chem.
2005,
70:
2893
<A NAME="RA49108ST-1L">1l</A>
Wirth T.
Angew.
Chem. Int. Ed.
2005,
44:
3656
<A NAME="RA49108ST-1M">1m</A>
Ladziata U.
Zhdankin VV.
ARKIVOC
2006,
(ix):
26
<A NAME="RA49108ST-1N">1n</A>
Richardson RD.
Wirth T.
Angew. Chem.
Int. Ed.
2006,
45:
4402
<A NAME="RA49108ST-1O">1o</A>
Matveeva ED.
Proskurina MV.
Zefirov NS.
Heteroat. Chem.
2006,
17:
595
<A NAME="RA49108ST-1P">1p</A>
Silva
LF.
Molecules
2006,
11:
421
<A NAME="RA49108ST-1Q">1q</A>
Zhdankin VV. In Science of Synthesis:
Houben-Weyl Methods of Molecular Transformations
Vol.
31a:
Ramsden CA.
Georg Thieme;
Stuttgart:
2007.
Chap.
31.4.1.
p.161-234
<A NAME="RA49108ST-1R">1r</A>
Deprez NR.
Sanford MS.
Inorg.
Chem.
2007,
46:
1924
<A NAME="RA49108ST-1S">1s</A>
Ochiai M.
Chem.
Rec.
2007,
7:
12
<A NAME="RA49108ST-1T">1t</A>
Ciufolini MA.
Braun NA.
Canesi S.
Ousmer M.
Chang J.
Chai D.
Synthesis
2007,
3759
<A NAME="RA49108ST-1U">1u</A>
Canty AJ.
Rodemann T.
Ryan JH.
Adv. Organomet. Chem.
2008,
5:
279
<A NAME="RA49108ST-1V">1v</A>
Quideau S.
Pouységu L.
Deffieux D.
Synlett
2008,
467
<A NAME="RA49108ST-2">2</A>
Varvoglis A.
The Organic Chemistry of Polycoordinated Iodine
VCH;
New
York:
1992.
Chap. 6.
p.307
<A NAME="RA49108ST-3A">3a</A>
Neilands O.
Chem. Heterocycl. Compd. (Engl.
Transl.)
2003,
39:
1555
<A NAME="RA49108ST-3B">3b</A>
Müller P.
Acc. Chem. Res.
2004,
37:
243
<A NAME="RA49108ST-4">4</A>
Spyroudis S.
Varvoglis A.
Synlett
1998,
221
<A NAME="RA49108ST-5">5</A>
Kokil PB.
Nair PM.
Tetrahedron Lett.
1977,
4113
<A NAME="RA49108ST-6">6</A>
Spyroudis S.
Varvoglis A.
J. Chem. Soc., Perkin Trans.
1
1984,
135
<A NAME="RA49108ST-7">7</A>
Spyroudis S.
Liebigs
Ann. Chem.
1986,
947
<A NAME="RA49108ST-8">8</A>
Spyroudis S.
J.
Org. Chem.
1986,
51:
3453
<A NAME="RA49108ST-9">9</A>
Papadopoulou M.
Spyroudis S.
Varvoglis A.
J.
Org. Chem.
1985,
50:
1509
<A NAME="RA49108ST-10">10</A>
Spyroudis S.
Tarantili P.
Tetrahedron
1994,
50:
11541
<A NAME="RA49108ST-11">11</A>
Prakash O.
Sharma V.
Tanwar MP.
Can.
J. Chem.
1999,
77:
1191
<A NAME="RA49108ST-12">12</A>
Daub KS.
Habermann B.
Hahn T.
Teich L.
Eger K.
Eur.
J. Org. Chem.
2004,
894
<A NAME="RA49108ST-13">13</A>
Benjahad A.
Guillemont J.
Andries K.
Nguyen CH.
Grierson DS.
Bioorg. Med. Chem. Lett.
2003,
13:
4309
<A NAME="RA49108ST-14">14</A>
Georgantji A.
Spyroudis S.
Tetrahedron Lett.
1995,
36:
443
<A NAME="RA49108ST-15">15</A>
Kappe T.
Korbuly G.
Stadlbauer W.
Chem.
Ber.
1978,
111:
3857
<A NAME="RA49108ST-16">16</A>
Laschober R.
Kappe T.
Synthesis
1990,
387
<A NAME="RA49108ST-17">17</A>
Alcock NW.
Bozopoulos AP.
Hatzigrigoriou E.
Varvoglis A.
Acta Crystallogr.,
Sect. C
1990,
46:
1300
<A NAME="RA49108ST-18">18</A>
Nishimura T.
Iwasaki H.
Takahashi M.
Takeda M.
J. Radioanal. Nucl. Chem.
2003,
25:
499
<A NAME="RA49108ST-19">19</A>
Papoutsis I.
Spyroudis S.
Varvoglis A.
J.
Heterocycl. Chem.
1996,
33:
579
<A NAME="RA49108ST-20">20</A>
Thomson RH.
Naturally Occurring Quinones IV
Blackie Academic & Professional;
London:
1997;
and previous editions.
<A NAME="RA49108ST-21">21</A>
Spyroudis S.
Molecules
2000,
5:
1291
<A NAME="RA49108ST-22">22</A>
Hatzigrigoriou E.
Spyroudis S.
Varvoglis A.
Liebigs
Ann. Chem.
1989,
167
<A NAME="RA49108ST-23">23</A>
Papoutsis I.
Spyroudis S.
Varvoglis A.
Tetrahedron
Lett.
1994,
35:
8449
<A NAME="RA49108ST-24">24</A>
Spyroudis S.
Xanthopoulou N.
J. Org. Chem.
2002,
67:
4612
<A NAME="RA49108ST-25">25</A>
Papoutsis I.
Spyroudis S.
Varvoglis A.
Tetrahedron
Lett.
1996,
37:
913
<A NAME="RA49108ST-26">26</A>
Papoutsis I.
Spyroudis S.
Varvoglis A.
Raptopoulou
CP.
Tetrahedron
1997,
53:
6097
<A NAME="RA49108ST-27">27</A>
Bakalbassis E.
Spyroudis S.
Tsiotra E.
J.
Org. Chem.
2006,
71:
7060
<A NAME="RA49108ST-28A">28a</A>
Emadi A.
Harwood JS.
Kohanim S.
Stagliano
KW.
Org. Lett.
2002,
4:
521
<A NAME="RA49108ST-28B">28b</A>
Stagliano KW.
Emadi A.
Lu Z.
Malinakova HC.
Twenter B.
Yu M.
Holland LE.
Rom AM.
Harwood JS.
Amin R.
Johnson
AA.
Pommier Y.
Bioorg.
Med. Chem.
2006,
14:
5651
<A NAME="RA49108ST-29A">29a</A>
Malamidou-Xenikaki E.
Spyroudis S.
Tsanakopoulou M.
J. Org. Chem.
2003,
68:
5627
<A NAME="RA49108ST-29B">29b</A>
Spagou K.
Malamidou-Xenikaki E.
Spyroudis S.
Molecules
2005,
10:
226
<A NAME="RA49108ST-30">30</A>
Koulouri S.
Malamidou-Xenikaki E.
Spyroudis S.
Tsanakopoulou M.
J. Org. Chem.
2005,
70:
8780
<A NAME="RA49108ST-31">31</A>
Pirrung MC.
Liu Y.
Deng L.
Halstead DK.
Li Z.
May JF.
Wedel M.
Austin DA.
Webster NJG.
J. Am. Chem. Soc.
2005,
127:
4609 ; and references cited therein
<A NAME="RA49108ST-32">32</A>
Kobayashi K.
Uneda T.
Kawakita M.
Morikawa O.
Konishi H.
Tetrahedron
Lett.
1997,
38:
837
<A NAME="RA49108ST-33A">33a</A>
Stagliano KW.
Malinakova HC.
Tetrahedron Lett.
1997,
38:
6617
<A NAME="RA49108ST-33B">33b</A>
Stagliano KW.
Malinakova HC.
J. Org. Chem.
1999,
64:
8034
<A NAME="RA49108ST-34">34</A>
Kazantzi G.
Malamidou-Xenikaki E.
Spyroudis S.
Synlett
2006,
2597
<A NAME="RA49108ST-35">35</A>
Glinis, E.; Malamidou-Xenikaki, E.;
Spyroudis, S. unpublished results.
<A NAME="RA49108ST-36A">36a</A>
Kirmse W.
Eur. J. Org. Chem.
2002,
2193
<A NAME="RA49108ST-36B">36b</A>
Tidwell TT.
Eur. J. Org. Chem.
2006,
563
<A NAME="RA49108ST-37">37</A>
Bakalbassis E.
Spyroudis S.
Tsipis C.
Eur.
J. Org. Chem.
2008,
1783
<A NAME="RA49108ST-38">38</A>
Mehta G.
Singh R.
Angew. Chem. Int. Ed.
2006,
45:
953
<A NAME="RA49108ST-39">39</A>
Spyroudis S.
Xanthopoulou N.
ARKIVOC
2003,
(vi):
95
<A NAME="RA49108ST-40">40</A>
Malamidou-Xenikaki E.
Spyroudis S.
Tsanakopoulou M.
Krautscheid H.
J. Org. Chem.
2007,
72:
502
<A NAME="RA49108ST-41">41</A>
Tsanakopoulou M.
Cottin T.
Büttner A.
Sarli V.
Malamidou-Xenikaki E.
Spyroudis S.
Giannis A.
ChemMedChem
2008,
3:
429
<A NAME="RA49108ST-42">42</A>
Malamidou-Xenikaki, E.; Spyroudis,
S.; Tsanakopoulou, M.; 8th Tetrahedron Symposium;
Berlin, Germany, June 2007; P2.89.
<A NAME="RA49108ST-43">43</A>
Malamidou-Xenikaki, E.; Spyroudis,
S.; Tsanakopoulou, M.; Krautscheid, H.; 8th
Tetrahedron Symposium; Berlin, Germany, June 2007; P1.84.
