Formal inverse sonogashira reaction: Direct alkynylation of arenes and heterocycles with alkynyl halides

Angewandte Chemie - International Edition

Volumn 49, Issue 12, 2010, Pages 2096-2098

  Dudnik, Alexander S ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Alkynylation; Arenes; C H activation; Heterocycles; Homogeneous catalysis

Indexed keywords

ALKYNYLATIONS; ALKYNYLS; C-H ACTIVATION; C-H BOND; CHEMICAL EQUATIONS; FUNCTIONALIZATIONS; HETEROCYCLES; HOMOGENEOUS CATALYSIS; SONOGASHIRA REACTIONS;

ACTIVATION ANALYSIS; CATALYSIS; REACTION KINETICS; TRANSITION METALS;

AROMATIC COMPOUNDS;

ALKYNE; BIPHENYL DERIVATIVE; HETEROCYCLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYNES; BIPHENYL COMPOUNDS; CATALYSIS; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; PALLADIUM;

EID: 77949382971     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906755     Document Type: Article

References (16)

1. a) V. K. Kalinin, D. N. Pashchenko, F.M. She, Mendeleev Commun. 1992, 2, 60; for the palladium-catalyzed direct alkynylation of 3-phenylsydnone (1) in 34 % yield, see :
2. b) A. Rodriguez, R. V. Fennesy, W. J. Moran, Tetrahedron Lett. 2009, 50, 3942.
3. a) B. A, Trofimov, Z. V. Stepanova, L. N. Sobenina, A. I. Mi-khaleva, I.A. Ushakov, Tetrahedron Lett. 2004, 45, 6513;
4. b) B. A. Trofimov, L. N. Sobenina, Z. V. Stepanova, T. I. Vakul'skaya, O. N. Kazheva, G. G. Aleksandrov, O. A. Dyachenko, A. I. Mikhaleva, Tetrahedron 2008, 64, 5541, and references therein.
5. a) K. Kobayashi, M. Arisawa, M. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 8528;
6. b) R. Amemiya, A. Fujii, M. Yamaguchi, Tetrahedron Lett. 2004, 45, 4333.
7. I. V. Seregin, V. Ryabova, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 7742.
8. For reviews, see: a) I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173;
9. b) L.-C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35.
10. Y. Gu, X. Wang, Tetrahedron Lett. 2009, 50, 763.
11. M. Tobisu, Y. Ano, N. Chatani, Org. Lett. 2009, 11, 3250.
12. N. Matsuyama, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 4156.
13. F. Besselièvre, S. Piguel, Angew. Chem. 2009, 121, 9717;
14. Angew. Chem. Int. Ed. 2009, 48, 9553.
15. J. P. Brand, J. Charpentier, J. Waser, Angew. Chem. 2009, 121, 9510;
16. Angew. Chem. Int. Ed. 2009, 48, 9346.