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

Authors

Ruili Gao, Marquette UniversityFollow
Chae S. Yi, Marquette UniversityFollow

Document Type

Article

Language

eng

Format of Original

3 p.

Publication Date

5-7-2010

Publisher

American Chemical Society

Source Publication

Journal of Organic Chemistry

Source ISSN

0022-3263

Original Item ID

DOI: 10.1021/jo100269y

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

Accepted version. Journal of Organic Chemistry, Vol. 75, No. 9 (May 2010): 3144-3146. DOI. © 2010 American Chemical Society. Used with permission.

Recommended Citation

Gao, Ruili and Yi, Chae S., "Regioselective Formation of α-Vinylpyrroles from the Ruthenium-Catalyzed Coupling Reaction of Pyrroles and Terminal Alkynes Involving C–H Bond Activation" (2010). Chemistry Faculty Research and Publications. 385.
https://epublications.marquette.edu/chem_fac/385