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Regioselective formation of alpha-vinylpyrroles from the ruthenium-catalyzed coupling reaction of pyrroles and terminal alkynes involving C-H bond activation.

ABSTRACT: The cationic ruthenium catalyst Ru(3)(CO)(12)/NH(4)PF(6) was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective alpha-vinylpyrroles. The carbon isotope effect on the alpha-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (rho = -0.90) indicate a rate-limiting C-C bond formation step of the coupling reaction.

SUBMITTER: Gao R

PROVIDER: S-EPMC2865850 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Regioselective formation of alpha-vinylpyrroles from the ruthenium-catalyzed coupling reaction of pyrroles and terminal alkynes involving C-H bond activation.

Gao Ruili R Yi Chae S CS

The Journal of organic chemistry 20100501 9

The cationic ruthenium catalyst Ru(3)(CO)(12)/NH(4)PF(6) was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective alpha-vinylpyrroles. The carbon isotope effect on the alpha-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (rho = -0.90) indicate a rate-limiting C-C bond formation step of the coupling reaction. ...[more]

PMID: 20384382

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