Efficient Palladium-Catalyzed
Coupling of Baylis-Hillman Acetates with an Allylstannane

Jinhyung Park; Young Bum Kwon; Kyungmo Yang; Hakjune Rhee; Cheol Min Yoon

doi:10.1055/s-0029-1218612

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Synthesis 2010(4): 661-665
DOI: 10.1055/s-0029-1218612

PAPER

Efficient Palladium-Catalyzed Coupling of Baylis-Hillman Acetates with an Allylstannane

Jinhyung Park^a, Young Bum Kwon^a, Kyungmo Yang^a, Hakjune Rhee^b, Cheol Min Yoon*^a
^a Department of Advanced Material Chemistry, Korea University, Jochiwon, Choongnam 339-700, South Korea
Fax: +81(41)8675396; e-Mail: cmyoon@korea.ac.kr;
^b Department of Chemistry & Applied Chemistry, Hanyang University, Sangrok-Gu, Ansan, Kyunggi-Do 426-791, South Korea

Further Information

Publication History

Received 23 July 2009
Publication Date:
16 December 2009 (online)

Abstract
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Abstract

Acetates of Baylis-Hillman adducts derived from ethyl acrylate, methyl vinyl ketone, and acrylonitrile were coupled with allyltributylstannane using Pd(PPh₃)₄ or Pd(dba)₂ as the catalyst at room temperature to afford the corresponding trisubstituted alka-1,5-dienes in good to high yields.

Key words

Baylis-Hillman acetates - allyltributylstannane - bis-π-allylpalladium - 1,5-diene - allylation

References

1 Baylis AB, and Hillman MED. inventors; DE 2,155,113. ; Chem. Abstr. 1972, 77, 34174q
2a Lee KY. Kim JM. Kim JN. Tetrahedron Lett. 2003, 44: 6737

Google Scholar
2b Lee KY. Kim JM. Kim JN. Tetrahedron 2003, 59: 385

Google Scholar
2c Im Y. J., Lee K. Y., Kim T. H., Kim J. N.; Tetrahedron Lett.; 2002, 43: 4675
2d Kim JN. Kim JM. Lee KY. Synlett 2003, 821

Google Scholar
2e Kim JN. Kim HS. Gong JH. Chung YM. Tetrahedron Lett. 2001, 42: 8341

Google Scholar
2f Drewes SE. Emslie ND. J. Chem. Soc., Perkin Trans. 1 1982, 2079

Google Scholar
2g Hoffmann HMR. Rabe J. Helv. Chim. Acta 1984, 67: 413

Google Scholar
2h Hoffmann HMR. Rabe J. J. Org. Chem. 1985, 50: 3849

Google Scholar
2i Hoffmann HMR. Rabe J. Angew. Chem., Int. Ed. Engl. 1985, 24: 94

Google Scholar
2j Buchholz R. Hoffmann HMR. Helv. Chim. Acta 1991, 74: 1213

Google Scholar
2k Ameer F. Drewes SE. Hoole RFA. Kaye PT. Pitchford AT. J. Chem. Soc., Perkin Trans. 1 1985, 2713

Google Scholar
3a Basavaiah D. Dharma Rao P. Suguna HR. Tetrahedron 1996, 52: 8001

Google Scholar
3b Basavaiah D. Jaganmohan Rao A. Satyanarayana T. Chem. Rev. 2003, 103: 811

Google Scholar
3c O’Dell DK. Nicholas KM. J. Org. Chem. 2003, 68: 6427

Google Scholar
4 Kabalka GW. Venkataiah B. Dong G. Org. Lett. 2003, 5: 3803

Crossref PubMed Google Scholar
5a Navarre L. Darses S. Genet J.-P. Chem. Commun. 2004, 1108

Google Scholar
5b Navarre L. Darses S. Genet J.-P. Adv. Synth. Catal. 2006, 348: 317

Google Scholar
6 Kabalka GW. Dong G. Venkataiah B. Chen C. J. Org. Chem. 2005, 70: 9207

Crossref Google Scholar
7 Das B. Banerjee J. Mahender G. Majhi A. Org. Lett. 2004, 6: 3349

Crossref Google Scholar
8 Ranu BC. Chattopadhyay K. Jana R. Tetrahedron Lett. 2007, 48: 3847

Crossref Google Scholar
9a Yadav JS. Subba Reddy BV. Mandal SS. Singh AP. Basak AK. Synthesis 2008, 1943

Google Scholar
9b Srihari P. Singh AP. Basak AK. Yadav JS. Tetrahedron Lett. 2007, 48: 5999

Google Scholar
10a Metal-Catalyzed Cross-Coupling Reactions Diedrich F. Stang PJ. Wiley-VCH; Weinheim: 1998.

Google Scholar
10b Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

Google Scholar
11a Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

Google Scholar
11b Mitchell TN. Synthesis 1992, 803

Google Scholar
11c Ritter K. Synthesis 1993, 735

Google Scholar
12 Mendez M. Cuerva JM. Gomez-Bengoa E. Cardenas DJ. Echavarren AM. Chem. Eur. J. 2002, 8: 3620

Crossref Google Scholar
13a Basavaiah D. Sarma PKS. Bhavani AKD. J. Chem. Soc., Chem. Commun. 1994, 1091

Google Scholar
13b Basavaiah D. Pandiaraju S. Padmaja K. Synlett 1996, 393

Google Scholar
13c Basavaiah D. Krishnamacharyulu M. Suguna HR. Pandiaraju S. Tetrahedron Lett. 1997, 38: 2141

Google Scholar
13d Shanmugam P. Singh PR. Synlett 2001, 1314

Google Scholar
14a Mandai T. Matsumoto T. Tsuji J. Tetrahedron Lett. 1993, 34: 2513

Google Scholar
14b Al-Masum M. Meguro M. Yamamoto Y. Tetrahedron Lett. 1997, 38: 6071

Google Scholar
15a Nakamura H. Iwama H. Yamamoto Y. Chem. Commun. 1996, 1459

Google Scholar
15b Nakamura H. Iwama H. Yamamoto Y. J. Am. Chem. Soc. 1996, 118: 6641 ; and references cited therein

Google Scholar
16 Nakamura H. Aoyagi K. Shim JG. Yamamoto Y. J. Am. Chem. Soc. 2001, 123: 372

Crossref Google Scholar