Transition-Metal-Catalyzed
Additions of Carbonyl Functionalities to Alkynes

Tetsuaki Fujihara; Tomohiro Iwai; Jun Terao; Yasushi Tsuji

doi:10.1055/s-0030-1258776

ACCOUNT

Transition-Metal-Catalyzed Additions of Carbonyl Functionalities to Alkynes

Tetsuaki Fujihara, Tomohiro Iwai, Jun Terao, Yasushi Tsuji*
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
Fax: +81(75)3832514; e-Mail: ytsuji@scl.kyoto-u.ac.jp;

Abstract

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Abstract

Transition-metal-catalyzed transformations between carbonyl compounds and carbon-carbon unsaturated bonds are important and attractive. In this account, we describe our recent results on the iridium- and palladium-catalyzed additions of acid chlorides, carbamoyl chlorides, and formamides to alkynes.

1 Introduction

2 Decarbonylation of Aldehydes

3 Addition Reactions

3.1 Addition of Acid Chlorides to Terminal Alkynes

3.2 Addition of Formamides to Alkynes

4 Annulation of N-Arylcarbamoyl Chlorides with Internal Alkynes

5 Conclusion

Key words

addition reactions - alkynes - annulations - iridium - palladium

Full Text

References

<A NAME="RA57010ST-1A">1a</A> Kollár K. Modern Carbonylation Methods Wiley-VCH; Weinheim: 2008.

<A NAME="RA57010ST-1B">1b</A> Beller M. Catalytic Carbonylation Reactions Springer; Heidelberg: 2006.

<A NAME="RA57010ST-1C">1c</A> Colquhoun HM. Thompson DJ. Twigg MV. Carbonylation: Direct Synthesis of Carbonyl Compounds Plenum; New York: 1991.

<A NAME="RA57010ST-2">2</A> Morimoto T. Kakiuchi K. Angew. Chem. Int. Ed. 2004, 43: 5580

<A NAME="RA57010ST-3A">3a</A> Sheldon RA. Pure Appl. Chem. 2000, 72: 1233

<A NAME="RA57010ST-3B">3b</A> Trost BM. Acc. Chem. Res. 2002, 35: 695

<A NAME="RA57010ST-4A">4a</A> Willis MC. Chem. Rev. 2010, 110: 725

<A NAME="RA57010ST-4B">4b</A> Park YJ. Park J.-W. Jun C.-H. Acc. Chem. Res. 2008, 41: 222

<A NAME="RA57010ST-5A">5a</A> Padwa A. Zhang H. J. Org. Chem. 2007, 72: 2570

<A NAME="RA57010ST-5B">5b</A> Zhang H. Padwa A. Tetrahedron Lett. 2006, 47: 3905

<A NAME="RA57010ST-5C">5c</A> Ikeda S. Shibuya M. Iwabuchi Y. Chem. Commun. 2007, 504

<A NAME="RA57010ST-5D">5d</A> Malerich JP. Maimone TJ. Elliott GI. Trauner D. J. Am. Chem. Soc. 2005, 127: 6276

<A NAME="RA57010ST-5E">5e</A> Harmata M. Wacharasindhu S. Org. Lett. 2005, 7: 2563

<A NAME="RA57010ST-5F">5f</A> Weatherhead GS. Cortez GA. Schrock RR. Hoveyda AH. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5805

<A NAME="RA57010ST-6A">6a</A> Tsuji J. Ohno K. Tetrahedron Lett. 1965, 6: 3969

<A NAME="RA57010ST-6B">6b</A> Ohno K. Tsuji J. J. Am. Chem. Soc. 1968, 90: 99

<A NAME="RA57010ST-7">7</A> Doughty DH. Pignolet LH. J. Am. Chem. Soc. 1978, 100: 7083

<A NAME="RA57010ST-8A">8a</A> Fristrup P. Kreis M. Palmelund A. Norrby P. Madsen R. J. Am. Chem. Soc. 2008, 130: 5206

<A NAME="RA57010ST-8B">8b</A> Kreis M. Palmelund A. Bunch L. Madsen R. Adv. Synth. Catal. 2006, 348: 2148

<A NAME="RA57010ST-9">9</A> Iwai T. Fujihara T. Tsuji Y. Chem. Commun. 2008, 6215

<A NAME="RA57010ST-10">10</A> Abu-Hasanayn F. Goldman ME. Goldman AS. J. Am. Chem. Soc. 1992, 114: 2520

<A NAME="RA57010ST-11">11</A> Pohland AE. Benson WR. Chem. Rev. 1966, 66: 161

<A NAME="RA57010ST-12A">12a</A> Zhou H. Zeng C. Ren L. Liao W. Huang X. Synlett 2006, 3504

<A NAME="RA57010ST-12B">12b</A> Martens H. Janssens F. Hoornaert G. Tetrahedron 1975, 31: 177

<A NAME="RA57010ST-12C">12c</A> Price CC. Pappalardo JA. J. Am. Chem. Soc. 1950, 72: 2613

<A NAME="RA57010ST-12D">12d</A> Wang B. Wang S. Li P. Wang L. Chem. Commun. 2010, 46: 5891

<A NAME="RA57010ST-13">13</A> Collman JP. Hegedus LS. Norton JR. Finke RG. Principles and Applications of Organotransition Metal Chemistry University Science Books; Mill Valley: 1987. Chap. 5.

<A NAME="RA57010ST-14">14</A> Kokubo K. Matsumasa K. Miura M. Nomura M. J. Org. Chem. 1996, 61: 6941

<A NAME="RA57010ST-15A">15a</A> Kashiwabara T. Fuse K. Hua R. Tanaka M. Org. Lett. 2008, 10: 5469

<A NAME="RA57010ST-15B">15b</A> Kashiwabara T. Kataoka K. Hua R. Shimada S. Tanaka M. Org. Lett. 2005, 7: 2241

<A NAME="RA57010ST-16">16</A> N-Heterocyclic Carbenes in Synthesis Nolan SP. Wiley-VCH; Weinheim: 2006.

<A NAME="RA57010ST-17">17</A> Iwai T. Fujihara T. Terao J. Tsuji Y. J. Am. Chem. Soc. 2009, 131: 6668

<A NAME="RA57010ST-18">18</A> Martin R. Buchwald SL. Acc. Chem. Res. 2008, 41: 1461

<A NAME="RA57010ST-19">19</A> Lee KY. Lee MJ. Kim JN. Tetrahedron 2005, 61: 8705

<A NAME="RA57010ST-20A">20a</A> Zhang M. Jiang H.-F. Neumann H. Beller M. Dixneuf PH. Angew. Chem. Int. Ed. 2009, 48: 1681

<A NAME="RA57010ST-20B">20b</A> Dudnik AS. Sromek AW. Rubina M. Kim JT. Kel’in AV. Gevorgyan V. J. Am. Chem. Soc. 2008, 130: 1440 ; and references cited therein

<A NAME="RA57010ST-21">21</A> Tsuji Y. Yoshii S. Ohsumi T. Kondo T. Watanabe Y. J. Organomet. Chem. 1987, 331: 379

<A NAME="RA57010ST-22">22</A> Kondo T. Okada T. Mitsudo T. Organometallics 1999, 18: 4123

<A NAME="RA57010ST-23">23</A> Ko S. Han H. Chang S. Org. Lett. 2003, 5: 2687

<A NAME="RA57010ST-24">24</A> Kobayashi Y. Kamisaki H. Yanada K. Yanada R. Takemoto Y. Tetrahedron Lett. 2005, 46: 7549

<A NAME="RA57010ST-25">25</A> Nakao Y. Idei H. Kanyiva KS. Hiyama T. J. Am. Chem. Soc. 2009, 131: 5070

<A NAME="RA57010ST-26">26</A> Fujihara T. Katafuchi Y. Iwai T. Terao J. Tsuji Y.
J. Am. Chem. Soc. 2010, 132: 2094

<A NAME="RA57010ST-27A">27a</A> Hills ID. Fu GC. J. Am. Chem. Soc. 2004, 126: 13178

<A NAME="RA57010ST-27B">27b</A> Grushin VV. Chem. Rev. 1996, 96: 2011

<A NAME="RA57010ST-27C">27c</A> Kudo K. Hidai M. Murayama T. Uchida Y. J. Chem. Soc. D 1970, 1701

<A NAME="RA57010ST-28">28</A> Lindhardt AT. Mantel MLH. Skrydstrup T. Angew. Chem. Int. Ed. 2008, 47: 2668

<A NAME="RA57010ST-29A">29a</A> Park JH. Kim SY. Kim SM. Chung YK. Org. Lett. 2007, 9: 2465

<A NAME="RA57010ST-29B">29b</A> Li Y. Alper H. Yu Z. Org. Lett. 2006, 8: 5199

<A NAME="RA57010ST-30">30</A> Negishi E. In Organopalladium Chemistry for Organic Synthesis Negishi E. de Meijere A. Wiley-Interscience; New York: 2002. p.135-137

<A NAME="RA57010ST-31">31</A> Canty AJ. Acc. Chem. Res. 1992, 25: 86

<A NAME="RA57010ST-32A">32a</A> Eicher T. Hauptmann S. The Chemistry of Heterocycles Wiley-VCH; Weinheim: 2003.

<A NAME="RA57010ST-32B">32b</A> Costero AM. Advances in Heterocyclic Chemistry 1993, 58: 171

<A NAME="RA57010ST-33">33</A> Guimond N. Gouliaras C. Fagnou K. J. Am. Chem. Soc. 2010, 132: 6908

<A NAME="RA57010ST-34A">34a</A> Kajita Y. Matsubara S. Kurahashi T. J. Am. Chem. Soc. 2008, 130: 6058

<A NAME="RA57010ST-34B">34b</A> Kajita Y. Kurahashi T. Matsubara S. J. Am. Chem. Soc. 2008, 130: 17226

<A NAME="RA57010ST-34C">34c</A> Yoshino Y. Kurahashi T. Matsubara S. J. Am. Chem. Soc. 2009, 131: 7494

<A NAME="RA57010ST-34D">34d</A> Miura T. Yamauchi M. Murakami M. Org. Lett. 2008, 10: 3085

<A NAME="RA57010ST-35">35</A> Lemoucheux L. Rouden J. Ibazizene M. Sobrio F. Lasne M.-C. J. Org. Chem. 2003, 68: 7289

<A NAME="RA57010ST-36A">36a</A> Kochi T. Urano S. Seki H. Mizushima E. Sato M. Kakiuchi F. J. Am. Chem. Soc. 2009, 131: 2792

<A NAME="RA57010ST-36B">36b</A> Yasui Y. Takemoto Y. Chem. Rec. 2008, 8: 386

<A NAME="RA57010ST-37">37</A> Yasui Y. Kakinokihara I. Takeda H. Takemoto Y. Synthesis 2009, 3989

<A NAME="RA57010ST-38">38</A> Iwai T. Fujihara T. Terao J. Tsuji Y. J. Am. Chem. Soc. 2010, 132: 9602

<A NAME="RA57010ST-39">39</A> Hiwatari K. Kayaki Y. Okita K. Ukai T. Shimizu I. Yamamoto A. Bull. Chem. Soc. Jpn. 2004, 77: 2237 ; and references cited therein

<A NAME="RA57010ST-40">40</A> Rahim M. Bushweller H. Ahmed KJ. Organometallics 1994, 13: 4952