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Synthesis 2011(16): 2561-2566
DOI: 10.1055/s-0030-1260077
DOI: 10.1055/s-0030-1260077
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Cobalt-Catalyzed Alkenylation of Thiazoles with Alkynes via C-H Bond Functionalization
Further Information
Received
15 March 2011
Publication Date:
17 June 2011 (online)
Publication History
Publication Date:
17 June 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201116/lookinside/thumbnails/10.1055-s-0030-1260077-1.jpg)
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
- For recent reviews, see:
-
1a
Hirano K.Miura M. Synlett 2011, 294 -
1b
Colby DA.Bergman RG.Ellman JA. Chem. Rev. 2010, 110: 624 -
1c
Lyons TW.Sanford MS. Chem. Rev. 2010, 110: 1147 -
1d
Sun CL.Li BJ.Shi ZJ. Chem. Commun. 2010, 46: 677 -
1e
Ackermann L. Chem. Commun. 2010, 46: 4866 -
1f
Chen X.Engle KM.Wang DH.Yu JQ. Angew. Chem. Int. Ed. 2009, 48: 5094 -
1g
Ackermann L.Vicente R.Kapdi AR. Angew. Chem. Int. Ed. 2009, 48: 9792 -
1h
Daugulis O.Do HQ.Shabashov D. Acc. Chem. Res. 2009, 42: 1074 -
1i
Kakiuchi F.Kochi T. Synthesis 2008, 3013 - 2
Ding ZH.Yoshikai N. Org. Lett. 2010, 12: 4180 - Related reaction with Ni catalyst:
-
3a
Nakao Y.Kanyiva KS.Oda S.Hiyama T. J. Am. Chem. Soc. 2006, 128: 8146 -
3b
Kanyiva KS.Nakao Y.Hiyama T. Heterocycles 2007, 72: 677 -
3c
Mukai T.Hirano K.Satoh T.Miura M. J. Org. Chem. 2009, 74: 6410 -
3d
Nakao Y.Kashihara N.Kanyiva KS.Hiyama T. Angew. Chem. Int. Ed. 2010, 49: 4451 - Related reaction with Rh catalyst:
-
4a
Tan KL.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2002, 124: 13964 -
4b
Tan KL.Park S.Ellman JA.Bergman RG.
J. Org. Chem. 2004, 69: 7329 -
5a
Cahiez G.Moyeux A. Chem. Rev. 2010, 110: 1435 -
5b
Hess W.Treutwein J.Hilt G. Synthesis 2008, 3537 -
5c
Yorimitsu H.Oshima K. Pure Appl. Chem. 2006, 78: 441 - For leading references on direct C2-functionalization of thiazoles, see:
-
7a
Do HQ.Daugulis O. J. Am. Chem. Soc. 2007, 129: 12404 -
7b
Lewis JC.Berman AM.Bergman RG.Ellman JA. J. Am. Chem. Soc. 2008, 130: 2493 -
7c
Besselievre F.Piguel S. Angew. Chem. Int. Ed. 2009, 48: 9553 -
7d
Canivet J.Yamaguchi J.Ban I.Itami K. Org. Lett. 2009, 11: 1733 -
7e
Hachiya H.Hirano K.Satoh T.Miura M. Org. Lett. 2009, 11: 1737 -
7f
Matsuyama N.Hirano K.Satoh T.Miura M. Org. Lett. 2009, 11: 4156 -
7g
Boogaerts IIF.Nolan SP.
J. Am. Chem. Soc. 2010, 132: 8858 -
7h
Do HQ.Daugulis O. Org. Lett. 2010, 12: 2517 -
7i
Huang JK.Chan J.Chen Y.Borths CJ.Baucom KD.Larsen RD.Faul MM. J. Am. Chem. Soc. 2010, 132: 3674 -
7j
Matsuyama N.Kitahara M.Hirano K.Satoh T.Miura M. Org. Lett. 2010, 12: 2358 -
7k
Mukai T.Hirano K.Satoh T.Miura M. Org. Lett. 2010, 12: 1360 -
7l
Truong T.Alvarado J.Tran LD.Daugulis O. Org. Lett. 2010, 12: 1200 -
7m
Xie K.Yang ZY.Zhou XJ.Li XJ.Wang SZ.Tan Z.An XY.Guo CC. Org. Lett. 2010, 12: 1564 - 8
Yoshikai N. Synlett 2011, 1047 -
9a
Gao K.Lee PS.Fujita T.Yoshikai N. J. Am. Chem. Soc. 2010, 132: 12249 -
9b
Gao K.Yoshikai N. J. Am. Chem. Soc. 2011, 133: 400 -
9c
Gao K.Yoshikai N. Angew. Chem. Int. Ed. 2011, DOI: 10.1002/anie.201101823 -
10a
Chen Q.Ilies L.Nakamura E. J. Am. Chem. Soc. 2011, 133: 428 -
10b
Li B.Wu Z.-H.Gu Y.-F.Sun C.-L.Wang B.-Q.Shi Z.-J. Angew. Chem. Int. Ed. 2011, 50: 1109 -
10c
Kim JY.Cho SH.Joseph J.Chang S. Angew. Chem. Int. Ed. 2010, 49: 9899 -
10d
Truong T.Alvardo J.Tran LD.Daugulis O. Org. Lett. 2010, 12: 1200 -
10e
Ilies L.Chen Q.Zeng X.Nakamura E. J. Am. Chem. Soc. 2011, 133: 5221 -
11a
Roger J.Pozgan F.Doucet H. J. Org. Chem. 2009, 74: 1179 -
11b
Liegault B.Lapointe D.Caron L.Vlassova A.Fagnou K. J. Org. Chem. 2009, 74: 1826 -
11c
Parisien M.Valette D.Fagnou K. J. Org. Chem. 2005, 70: 7578 -
11d
Pivsa-Art S.Satoh T.Kawamura Y.Miura M.Nomura M. Bull. Chem. Soc. Jpn. 1998, 71: 467 - 12
Zhao HY.Foss FW.Breslow R. J. Am. Chem. Soc. 2008, 130: 12590
References
A small part of the present work was communicated in ref 2.