Rhodium-Catalyzed Homocoupling
of (1-Acyloxyvinyl)silanes: Synthesis of 1,3-Diene-2,3-diyl Diesters
and Their Derivatives

Yanni Yue; Hiroki Yamamoto; Motoki Yamane

doi:10.1055/s-0029-1217968

LETTER

Rhodium-Catalyzed Homocoupling of (1-Acyloxyvinyl)silanes: Synthesis of 1,3-Diene-2,3-diyl Diesters and Their Derivatives

Yanni Yue, Hiroki Yamamoto, Motoki Yamane*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanynag Link, Singapore 637371, Singapore
Fax: +6567911961; e-Mail: yamane@ntu.edu.sg;

Abstract

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Abstract

1,3-Diene-2,3-diyl diesters are synthesized by rhodium-catalyzed homocoupling of (1-acyloxyvinyl)silanes. Double transmetalation between vinylsilane and rhodium intermediate in a single catalytic cycle is the key in this reaction. From the homocoupling products, symmetrical α-diketone and its monoacetal are easily synthesized.

Key words

homocoupling - rhodium catalyst - organosilicon compounds - vinyl ester - conjugated diene

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References

References and Notes

Current address: Department of Chemistry, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8551, Japan.

<A NAME="RD17109ST-2A">2a</A> Mori K. The Synthesis of Insect Pheromones, In The Total Synthesis of Natural Products Vol. 4: ApSimon J. John Wiley and Sons; New York: 1981.

Selected examples:

<A NAME="RD17109ST-2B">2b</A> Nagamitsu T. Takano D. Seki M. Arima S. Ohtawa M. Shiomi K. Harigaya Y. Omura S. Tetrahedron 2008, 64: 8117

<A NAME="RD17109ST-2C">2c</A> Yadav JS. Reddy KB. Sabitha G. Tetrahedron 2008, 64: 1971

<A NAME="RD17109ST-2D">2d</A> Shibahara S. Fujino M. Tashiro Y. Takahashi K. Ishihara J. Hatakeyama S. Org. Lett. 2008, 10: 2139

<A NAME="RD17109ST-2E">2e</A> Tortosa M. Yakelis NA. Roush WR. J. Org. Chem. 2008, 9657

<A NAME="RD17109ST-2F">2f</A> Stille JK. Groh BL. J. Am. Chem. Soc. 1987, 109: 813

<A NAME="RD17109ST-2G">2g</A> Onyango EO. Tsurumoto J. Imai N. Takahashi K. Ishihara J. Hatakeyama S. Angew. Chem. Int. Ed. 2007, 46: 6703

For examples of synthesis of conjugated dienes, see:

<A NAME="RD17109ST-3A">3a</A> Guseinov II. Vasil’ev GS. Russ. Chem. Rev. 1963, 32: 20

<A NAME="RD17109ST-3B">3b</A> Baba S. Negishi E.-I. J. Am. Chem. Soc. 1976, 98: 6729

<A NAME="RD17109ST-3C">3c</A> Babudri F. Farinola GM. Naso F. Ragni R. Spina G. Synthesis 2007, 3088

<A NAME="RD17109ST-3D">3d</A> Imoto J. Hayashi S. Hirano K. Yorimitsu H. Oshima K. Bull. Chem. Soc. Jpn. 2009, 82: 393

<A NAME="RD17109ST-4A">4a</A> Glorious F. Angew. Chem. Int. Ed. 2004, 43: 3364

<A NAME="RD17109ST-4B">4b</A> Hayashi T. Ueyama K. Tokunaga N. Yoshida K.
J. Am. Chem. Soc. 2003, 125: 11508

<A NAME="RD17109ST-4C">4c</A> Fischer C. Defieber C. Suzuki T. Carreira EM. J. Am. Chem. Soc. 2004, 126: 1628

Selected examples:

<A NAME="RD17109ST-5A">5a</A> Paley RS. Liu JM. Lichtenstein BR. Knoedler VL. Sanan TT. Adams DJ. Fernández J. Rablen PR. Org. Lett. 2007, 48: 595

<A NAME="RD17109ST-5B">5b</A> Saito S. Takeuchi K. Tetrahedron Lett. 2007, 48: 595

<A NAME="RD17109ST-5C">5c</A> Sibley R. Hatoum-Mokdad H. Schoenleber R. Musza L. Stirtan W. Marrero D. Carley E. Xiao H. Dumas J. Bioorg. Med. Chem. Lett. 2003, 13: 1919

Selected examples:

<A NAME="RD17109ST-6A">6a</A> Pragliola S. Cipriano M. Boccia AC. Longo P. Macromol. Rapid Commun. 2002, 23: 356

<A NAME="RD17109ST-6B">6b</A> Kamahori K. Tada S. Ito K. Itsuno S. Macromolecules 1999, 32: 541

<A NAME="RD17109ST-6C">6c</A> Friedmann G. Brosse N. Eur. Polym. J. 1991, 27: 747

<A NAME="RD17109ST-7">7</A> Fringuelli F. Taticci A. Dienes in the Diels-Alder Reaction John Wiley and Sons; New York: 1990.

Only special types of 1,3-diene-2,3-diyl diesters are reported. See:

<A NAME="RD17109ST-8A">8a</A> García Liñares GE. Nudelman NS.
J. Phys Org. Chem. 2003, 16: 569

<A NAME="RD17109ST-8B">8b</A> Saalfrank RW. Stark A. Bremer M. Hummel H.-U. Angew. Chem., Int. Ed. Engl. 1990, 29: 311

<A NAME="RD17109ST-8C">8c</A> Stachel H.-D. Justus Liebigs Ann. Chem. 1965, 689: 118

<A NAME="RD17109ST-8D">8d</A> Fiesselmann H. Lindner H.-J. Chem. Ber. 1956, 89: 1799

<A NAME="RD17109ST-9">9</A> Yamane M. Uera K. Narasaka K. Bull. Chem. Soc. Jpn. 2005, 78: 477

For fluoride-ion-promoted transmetalation between transition metals and vinylsilanes, see:

<A NAME="RD17109ST-10A">10a</A> Sugiyama A. Ohnishi Y.-y. Nakaoka M. Nakao Y. Sato H. Sasaki S. Nakao Y. Hiyama T. J. Am. Chem. Soc. 2008, 130: 12975

<A NAME="RD17109ST-10B">10b</A> Denmark SE. Sweis RF. Wehrli D. J. Am. Chem. Soc. 2004, 126: 4865

<A NAME="RD17109ST-10C">10c</A> Denmark SE. Choi JY. J. Am. Chem. Soc. 1999, 121: 5821

<A NAME="RD17109ST-10D">10d</A> Denmark SE. Wehrli D. Org. Lett. 2000, 2: 565

<A NAME="RD17109ST-10E">10e</A> Itami K. Nokami T. Ishimura Y. Mitsudo K. Kamei T. Yoshida J. J. Am. Chem. Soc. 2001, 123: 11577

<A NAME="RD17109ST-10F">10f</A> Koike T. Du X. Sanada T. Danda Y. Mori A. Angew. Chem. Int. Ed. 2003, 42: 89

For transmetalation between transition metals and alkoxy or hydroxy vinylsilanes, see:

<A NAME="RD17109ST-11A">11a</A> Sore HF. Boehner CM. MacDonald SJF. Norton D. Fox DJ. Spring DR. Org. Biomol. Chem. 2009, 7: 1068

<A NAME="RD17109ST-11B">11b</A> Denmark SE. Sweis RF. J. Am. Chem. Soc. 2004, 126: 4876

<A NAME="RD17109ST-11C">11c</A> Oi S. Honma Y. Inoue Y. Org. Lett. 2002, 4: 667

<A NAME="RD17109ST-11D">11d</A> Oi S. Taira A. Honma Y. Inoue Y. Org. Lett. 2003, 5: 97

<A NAME="RD17109ST-11E">11e</A> Denmark SE. Sweis RF. J. Am. Chem. Soc. 2001, 123: 6439

<A NAME="RD17109ST-11F">11f</A> Hirabayashi K. Mori A. Kawashima J. Suguro M. Nishihara Y. Hiyama T. J. Org. Chem. 2000, 65: 5342

For activation of tetraorganosilicon compounds, see:

<A NAME="RD17109ST-12A">12a</A> Nakao Y. Chem J. Tanaka M. Hiyama T. J. Am. Chem. Soc. 2007, 129: 11694

<A NAME="RD17109ST-12B">12b</A> Nakao Y. Sahoo AK. Imanaka H. Yada A. Hiyama T. Pure Appl. Chem. 2006, 78: 435

<A NAME="RD17109ST-12C">12c</A> Nakao Y. Imanaka H. Sahoo AK. Yada A. Hiyama T. J. Am. Chem. Soc. 2005, 127: 6952

For Pd-catalyzed oxidative coupling of organometallic compounds, see:

<A NAME="RD17109ST-13A">13a</A> Zhao Y. Wang H. Hou X. Hu Y. Lei A. Zhang H. Zhu L. J. Am. Chem. Soc. 2006, 128: 15048

<A NAME="RD17109ST-13B">13b</A> Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

<A NAME="RD17109ST-13C">13c</A> Song ZZ. Wong HNC. J. Org. Chem. 1994, 59: 33

<A NAME="RD17109ST-13D">13d</A> Ye X.-S. Wong HNC. J. Org. Chem. 1997, 62: 1940

<A NAME="RD17109ST-13E">13e</A> Yamaguchi S. Ohno S. Tamao K. Synlett 1997, 1199

<A NAME="RD17109ST-13F">13f</A> Moreno-Mañas M. Pérez M. Pleixats R. J. Org. Chem. 1996, 61: 2346

<A NAME="RD17109ST-13G">13g</A> Aramendia MA. Lafont F. Moreno-Mañas M. Pleixats R. Roglans A. J. Org. Chem. 1999, 64: 3592

<A NAME="RD17109ST-13H">13h</A> Smith KA. Campi EM. Jackson WR. Marcuccio S. Naeslund CGM. Deacon GB. Synlett 1997, 131

<A NAME="RD17109ST-13I">13i</A> Burns MJ. Fairlamb IJS. Kapdi AR. Sehnal P. Tayor RJK. Org. Lett. 2007, 9: 5397

<A NAME="RD17109ST-13J">13j</A> Yamamoto Y. Synlett 2007, 1913

<A NAME="RD17109ST-13K">13k</A> Adamo C. Amatore C. Ciofini I. Jutand A. Lakmini H. J. Am. Chem. Soc. 2006, 128: 6829

<A NAME="RD17109ST-13L">13l</A> Zhou C. Larock RC.
J. Org. Chem. 2006, 71: 3184

<A NAME="RD17109ST-13M">13m</A> Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Tetrahedron Lett. 2003, 44: 1541

<A NAME="RD17109ST-13N">13n</A> Koza DJ. Carita E. Synthesis 2002, 2183

<A NAME="RD17109ST-13O">13o</A> Lei A. Zhang X. Tetrahedron Lett. 2002, 43: 2525

<A NAME="RD17109ST-13P">13p</A> Mitsudo K. Shiraga T. Tanaka H. Tetrahedron Lett. 2008, 6593

<A NAME="RD17109ST-13Q">13q</A> Yoshida H. Yamaryo Y. Ohshita J. Kunai A. Chem. Commun. 2003, 1510

For Rh-catalyzed homocoupling of organometallic compounds, see:

<A NAME="RD17109ST-14A">14a</A> Vogler T. Studer A. Adv. Synth. Catal. 2008, 350: 1963

<A NAME="RD17109ST-14B">14b</A> Larock RC. Bernhardt JC. J. Org. Chem. 1977, 42: 1680

For Au, see:

<A NAME="RD17109ST-14C">14c</A> Sakurai H. Tsunoyama H. Tsukuda T. J. Organomet. Chem. 2007, 692: 368

<A NAME="RD17109ST-14D">14d</A> Carrettin S. Guzman J. Corma A. Angew. Chem. Int. Ed. 2005, 44: 2242

<A NAME="RD17109ST-14E">14e</A> González-Arellano C. Corma A. Iglesias M. Sánchez F. Chem. Commun. 2005, 1990

For Cu, see:

<A NAME="RD17109ST-14F">14f</A> Kirai N. Yamamoto Y. Eur. J. Org. Chem. 2009, 1964

<A NAME="RD17109ST-14G">14g</A> Demir AS. Reis U. Emrullahoglu M. J. Org. Chem. 2003, 68: 10130

For Cr, see:

<A NAME="RD17109ST-14H">14h</A> Falck JR. Mohapatra S. Bondlela M. Venkataraman SK. Tetrahedron Lett. 2002, 43: 8149

For V, see:

<A NAME="RD17109ST-14I">14i</A> Mizuno H. Sakurai H. Amaya T. Hirao T. Chem. Commun. 2006, 5042

For Co, see:

<A NAME="RD17109ST-14J">14j</A> Moncomble A. Le Floch P. Gosmini C. Chem. Eur. J. 2009, 15: 4770

For Mn, see:

<A NAME="RD17109ST-14K">14k</A> Zhou Z. Xue W. J. Organomet. Chem. 2009, 694: 599

For metal-mediated homocoupling of vinylsilanes, see:

<A NAME="RD17109ST-15A">15a</A> Weber WP. Felix RA. Willard AK. Koenig KE. Tetrahedron Lett. 1971, 4701

<A NAME="RD17109ST-15B">15b</A> Itami K. Ushiogi Y. Nokami T. Ohashi Y. Yoshida T. Org. Lett. 2004, 6: 3695

CCDC 737226 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.