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Synfacts 2010(1): 0025-0025
DOI: 10.1055/s-0029-1218459
DOI: 10.1055/s-0029-1218459
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed Synthesis of Pyrroles by [4+1] Cycloaddition
A. Mizuno, H. Kusama, N. Iwasawa*
Tokyo Institute of Technology, Japan
Further Information
Publication History
Publication Date:
21 December 2009 (online)
Significance
Iwasawa and co-workers report the rhodium(I)-catalyzed [4+1] cycloaddition of α,β-unsaturated imines with terminal alkynes to afford pyrrole derivatives. The best results were obtained using [{RhCl(coe)2}2] as catalyst and Cy3P as ligand. A mechanism involving nucleophilic addition of the imine nitrogen to the carbene carbon of the rhodium vinylidene complex A is proposed. In support of this mechanism, the isolated vinylidene complex {RhCl[=C=C(H)n-Hex](PCy3)2} also catalyzed the reaction under similar conditions. Further mechanistic studies have been promised.