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DOI: 10.1055/s-0030-1258758
Indium-Mediated Multicomponent Synthesis of Pyrroles
Contributor(s):Victor Snieckus, Johnathan BoardXiamen University, P. R. of China
A Novel Indium-Catalyzed Three-Component Reaction: General and Efficient One-Pot Synthesis of Substituted Pyrroles
Synlett 2010, 2345-2351
Publication History
Publication Date:
21 October 2010 (online)
Key words
pyrroles - multicomponent reaction - indium catalysis
Significance
Reported is the indium trichloride mediated multicomponent synthesis of highly substituted pyrroles. The reaction proceeds in one pot and does not require the exclusion of air or moisture. A number of catalysts were investigated and indium trichloride was shown to be superior, although a mixture of Ag(OTf) and Cu(OTf)2 was also efficacious. Under the reaction conditions a terminal acetylenic TMS group is cleaved. This work is an extension of a previous method from the same group for the formation of furans.
Comment
Pyrroles are important structures in a broad range of chemical disciplines. The current method for their synthesis should prove highly useful due to the simplicity of the reaction, the easily accessible starting materials, and the highly substituted nature of the products. The reaction was optimized with respect to the catalyst, catalyst loading, and solvent. The substrate scope was moderately examined with respect to the acetylene and the amine, but poorly investigated with respect to the silyl enol ether.