Title

Regioselective Formation of α-Vinylpyrroles from the Ruthenium-Catalyzed Coupling Reaction of Pyrroles and Terminal Alkynes Involving C–H Bond Activation

Document Type

Article

Publication Date

5-7-2010

Source Publication

Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

The cationic ruthenium catalyst Ru3(CO)12/NH4PF6 was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective α-vinylpyrroles. The carbon isotope effect on the α-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (ρ = −0.90) indicate a rate-limiting C−C bond formation step of the coupling reaction.

Comments

Journal of Organic Chemistry, Vol. 75, No. 9 (May 2010): 3144-3146. DOI.