Cobalt-Catalyzed Alkenylation
of Thiazoles with Alkynes via C-H Bond Functionalization

Zhenhua Ding; Naohiko Yoshikai

doi:10.1055/s-0030-1260077

SPECIALTOPIC

Cobalt-Catalyzed Alkenylation of Thiazoles with Alkynes via C-H Bond Functionalization

Zhenhua Ding, Naohiko Yoshikai*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +65(6791)1961; e-Mail: nyoshikai@ntu.edu.sg;

Abstract

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Abstract

A cobalt-Xantphos catalyst has been developed for the syn addition of (benzo)thiazoles to internal alkynes via C-H bond functionalization. The reaction affords C2-alkenylated (benzo)thiazoles with high regio- and stereoselectivities under mild conditions.

Key words

cobalt - C-H activation - heterocycles - hydroarylation - alkynes

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References

For recent reviews, see:

<A NAME="RC29411SS-1A">1a</A> Hirano K. Miura M. Synlett 2011, 294

<A NAME="RC29411SS-1B">1b</A> Colby DA. Bergman RG. Ellman JA. Chem. Rev. 2010, 110: 624

<A NAME="RC29411SS-1C">1c</A> Lyons TW. Sanford MS. Chem. Rev. 2010, 110: 1147

<A NAME="RC29411SS-1D">1d</A> Sun CL. Li BJ. Shi ZJ. Chem. Commun. 2010, 46: 677

<A NAME="RC29411SS-1E">1e</A> Ackermann L. Chem. Commun. 2010, 46: 4866

<A NAME="RC29411SS-1F">1f</A> Chen X. Engle KM. Wang DH. Yu JQ. Angew. Chem. Int. Ed. 2009, 48: 5094

<A NAME="RC29411SS-1G">1g</A> Ackermann L. Vicente R. Kapdi AR. Angew. Chem. Int. Ed. 2009, 48: 9792

<A NAME="RC29411SS-1H">1h</A> Daugulis O. Do HQ. Shabashov D. Acc. Chem. Res. 2009, 42: 1074

<A NAME="RC29411SS-1I">1i</A> Kakiuchi F. Kochi T. Synthesis 2008, 3013

<A NAME="RC29411SS-2">2</A> Ding ZH. Yoshikai N. Org. Lett. 2010, 12: 4180

Related reaction with Ni catalyst:

<A NAME="RC29411SS-3A">3a</A> Nakao Y. Kanyiva KS. Oda S. Hiyama T. J. Am. Chem. Soc. 2006, 128: 8146

<A NAME="RC29411SS-3B">3b</A> Kanyiva KS. Nakao Y. Hiyama T. Heterocycles 2007, 72: 677

<A NAME="RC29411SS-3C">3c</A> Mukai T. Hirano K. Satoh T. Miura M. J. Org. Chem. 2009, 74: 6410

<A NAME="RC29411SS-3D">3d</A> Nakao Y. Kashihara N. Kanyiva KS. Hiyama T. Angew. Chem. Int. Ed. 2010, 49: 4451

Related reaction with Rh catalyst:

<A NAME="RC29411SS-4A">4a</A> Tan KL. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2002, 124: 13964

<A NAME="RC29411SS-4B">4b</A> Tan KL. Park S. Ellman JA. Bergman RG.
J. Org. Chem. 2004, 69: 7329

<A NAME="RC29411SS-5A">5a</A> Cahiez G. Moyeux A. Chem. Rev. 2010, 110: 1435

<A NAME="RC29411SS-5B">5b</A> Hess W. Treutwein J. Hilt G. Synthesis 2008, 3537

<A NAME="RC29411SS-5C">5c</A> Yorimitsu H. Oshima K. Pure Appl. Chem. 2006, 78: 441

A small part of the present work was communicated in ref 2.

For leading references on direct C2-functionalization of thiazoles, see:

<A NAME="RC29411SS-7A">7a</A> Do HQ. Daugulis O. J. Am. Chem. Soc. 2007, 129: 12404

<A NAME="RC29411SS-7B">7b</A> Lewis JC. Berman AM. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2008, 130: 2493

<A NAME="RC29411SS-7C">7c</A> Besselievre F. Piguel S. Angew. Chem. Int. Ed. 2009, 48: 9553

<A NAME="RC29411SS-7D">7d</A> Canivet J. Yamaguchi J. Ban I. Itami K. Org. Lett. 2009, 11: 1733

<A NAME="RC29411SS-7E">7e</A> Hachiya H. Hirano K. Satoh T. Miura M. Org. Lett. 2009, 11: 1737

<A NAME="RC29411SS-7F">7f</A> Matsuyama N. Hirano K. Satoh T. Miura M. Org. Lett. 2009, 11: 4156

<A NAME="RC29411SS-7G">7g</A> Boogaerts IIF. Nolan SP.
J. Am. Chem. Soc. 2010, 132: 8858

<A NAME="RC29411SS-7H">7h</A> Do HQ. Daugulis O. Org. Lett. 2010, 12: 2517

<A NAME="RC29411SS-7I">7i</A> Huang JK. Chan J. Chen Y. Borths CJ. Baucom KD. Larsen RD. Faul MM. J. Am. Chem. Soc. 2010, 132: 3674

<A NAME="RC29411SS-7J">7j</A> Matsuyama N. Kitahara M. Hirano K. Satoh T. Miura M. Org. Lett. 2010, 12: 2358

<A NAME="RC29411SS-7K">7k</A> Mukai T. Hirano K. Satoh T. Miura M. Org. Lett. 2010, 12: 1360

<A NAME="RC29411SS-7L">7l</A> Truong T. Alvarado J. Tran LD. Daugulis O. Org. Lett. 2010, 12: 1200

<A NAME="RC29411SS-7M">7m</A> Xie K. Yang ZY. Zhou XJ. Li XJ. Wang SZ. Tan Z. An XY. Guo CC. Org. Lett. 2010, 12: 1564

<A NAME="RC29411SS-8">8</A> Yoshikai N. Synlett 2011, 1047

<A NAME="RC29411SS-9A">9a</A> Gao K. Lee PS. Fujita T. Yoshikai N. J. Am. Chem. Soc. 2010, 132: 12249

<A NAME="RC29411SS-9B">9b</A> Gao K. Yoshikai N. J. Am. Chem. Soc. 2011, 133: 400

<A NAME="RC29411SS-9C">9c</A> Gao K. Yoshikai N. Angew. Chem. Int. Ed. 2011, DOI: 10.1002/anie.201101823

<A NAME="RC29411SS-10A">10a</A> Chen Q. Ilies L. Nakamura E. J. Am. Chem. Soc. 2011, 133: 428

<A NAME="RC29411SS-10B">10b</A> Li B. Wu Z.-H. Gu Y.-F. Sun C.-L. Wang B.-Q. Shi Z.-J. Angew. Chem. Int. Ed. 2011, 50: 1109

<A NAME="RC29411SS-10C">10c</A> Kim JY. Cho SH. Joseph J. Chang S. Angew. Chem. Int. Ed. 2010, 49: 9899

<A NAME="RC29411SS-10D">10d</A> Truong T. Alvardo J. Tran LD. Daugulis O. Org. Lett. 2010, 12: 1200

<A NAME="RC29411SS-10E">10e</A> Ilies L. Chen Q. Zeng X. Nakamura E. J. Am. Chem. Soc. 2011, 133: 5221

<A NAME="RC29411SS-11A">11a</A> Roger J. Pozgan F. Doucet H. J. Org. Chem. 2009, 74: 1179

<A NAME="RC29411SS-11B">11b</A> Liegault B. Lapointe D. Caron L. Vlassova A. Fagnou K. J. Org. Chem. 2009, 74: 1826

<A NAME="RC29411SS-11C">11c</A> Parisien M. Valette D. Fagnou K. J. Org. Chem. 2005, 70: 7578

<A NAME="RC29411SS-11D">11d</A> Pivsa-Art S. Satoh T. Kawamura Y. Miura M. Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 467

<A NAME="RC29411SS-12">12</A> Zhao HY. Foss FW. Breslow R. J. Am. Chem. Soc. 2008, 130: 12590