Palladium-Catalyzed Domino
Heck/C-H Activation/Intermolecular Direct Arylation
Reactions

Zhiyao Lu; Yuxin Cui; Yanxing Jia

doi:10.1055/s-0030-1260603

SPECIALTOPIC

Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions

Zhiyao Lu, Yuxin Cui*, Yanxing Jia*
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, P. R. of China
Fax: +86(10)82805166; e-Mail: yxjia@bjmu.edu.cn;

Abstract

All articles of this category

Abstract

A regioselective, palladium-catalyzed domino Heck/C-H activation/intermolecular direct arylation reaction has been developed, providing rapid access to diverse biaryl heterocycles.

Key words

palladium - domino reaction - C-H activation - arylation

Full Text

References

For selected examples, see:

1a Cheng Y. Albrecht BK. Brown J. Buchanan JL. Buckner WH. DiMauro EF. Emkey R. Fremeau RT. Harmange J.-C. Hoffman BJ. Huang L. Huang M. Lee JH. Lin F.-F. Martin MW. Nguyen HQ. Patel VF. Tomlinson SA. White RD. Xia X. Hitchcock SA. J. Med. Chem. 2008, 51: 5019

1b Chimenti F. Maccioni E. Secci D. Bolasco A. Chimenti P. Granese A. Carradori S. Alcaro S. Ortuso F. Yanez M. Orallo F. Cirilli R. Ferretti R. La Torre F. J. Med. Chem. 2008, 51: 4874

1c Goodacre SC. Street LJ. Hallett DJ. Crawforth JM. Kelly S. Owens AP. Blackaby WP. Lewis RT. Stanley J. Smith AJ. Ferris P. Sohal B. Cook SM. Pike A. Brown N. Wafford KA. Marshall G. Castro JL. Atack JR. J. Med. Chem. 2006, 49: 35

For reviews, see:

2a Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; New York: 1998.

2b Hassan J. Gvignon MS. Gozzi C. Shulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

2c Baudoin O. Eur. J. Org. Chem. 2005, 20: 4223

For reviews on direct arylation, see:

3a Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 107: 174

3b Campeau L.-C. Stuart DR. Fagnou K. Aldrichimica Acta 2007, 40: 35

3c Campeau L.-C. Fagnou K. Chem. Commun. 2006, 1253

3d Satoh T. Miura M. Chem. Lett. 2007, 36: 200

3e Lewis JC. Bergman RC. Ellman JA. Acc. Chem. Res. 2008, 41: 1013

3f Li B.-J. Yang S.-D. Shi Z.-J. Synlett 2008, 949

3g Daugulis O. Zaitsev VG. Shabashov D. Pham Q.-N. Lazareva A. Synlett 2006, 3382

3h Pascual S. de Mendoza P. Echavarren AM. Org. Biomol. Chem. 2007, 5: 2727

3i Catellani M. Motti E. Della Ca’ N. Ferraccioli R. Eur. J. Org. Chem. 2007, 4153

3j McGlacken GP. Bateman LM. Chem. Soc. Rev. 2009, 38: 2447

4a Grigg R. Pure Appl. Chem. 1999, 70: 1647

4b Poli G. Giambastiani G. Heumann A. Tetrahedron 2000, 56: 5959

4c Catellani M. Synlett 2003, 298

4d Balme G. Bossharth E. Monteiro N. Eur. J. Org. Chem. 2003, 4101

4e Zeni G. Larock R. Chem. Rev. 2004, 104: 2285

4f Cacchi S. Fabrizi G. Chem. Rev. 2005, 105: 2873

5a Tian Q. Larock RC. Org. Lett. 2000, 2: 3329

5b Larock RC. Tian Q. J. Org. Chem. 2001, 66: 7372

5c Campo MA. Huang Q. Yao T. Tian Q. Larock RC. J. Am. Chem. Soc. 2003, 125: 11506

5d Huang Q. Fazio A. Dai G. Campo MA. Larock RC. J. Am. Chem. Soc. 2004, 126: 7460

5e Zhao J. Larock RC. Org. Lett. 2005, 7: 701

5f Kesharwani T. Larock RC. Tetrahedron 2008, 64: 6090

6 Rene O. Lapointe D. Fagnou K. Org. Lett. 2009, 11: 4560

7 Lu Z. Hu C. Guo J. Li J. Cui Y. Jia Y. Org. Lett. 2010, 12: 480