Stereoselective Synthesis of (Z)-Acrylic Nitriles from the Ruthenium-Catalyzed Coupling Reaction of Nitriles with Unsaturated Carbonyl Compounds via C–C Bond Cleavage

Authors

• Aldiyar Shakenov, Marquette University
• Krishna Prasad Gnyawali, Marquette University
• Chae S. Yi, Marquette UniversityFollow

Document Type

Article

Publication Date

1-2025

Publisher

American Chemical Society

Source Publication

The Journal of Organic Chemistry

Source ISSN

0022-3263

Original Item ID

DOI: 10.1021/acs.joc.4c01988

Abstract

Acrylic nitriles are a versatile class of synthetic precursors for a variety of pharmaceutically active compounds, as well as for nitrile polymers. We devised a stereoselective synthesis of (Z)-acrylic nitriles from the Ru-catalyzed coupling reaction of nitriles with unsaturated carbonyl compounds via C–C bond cleavage. Both carbon KIE and Hammett correlation data indicated that C–C bond cleavage is the rate-determining step for the coupling reaction. Several bioactive (Z)-acrylic nitriles were synthesized by using the catalytic coupling method.

Comments

The Journal of Organic Chemistry, Vol. 90, No. 5 (January 2025): 1733-1739. DOI.

Recommended Citation

Shakenov, Aldiyar; Gnyawali, Krishna Prasad; and Yi, Chae S., "Stereoselective Synthesis of (Z)-Acrylic Nitriles from the Ruthenium-Catalyzed Coupling Reaction of Nitriles with Unsaturated Carbonyl Compounds via C–C Bond Cleavage" (2025). Chemistry Faculty Research and Publications. 1129.
https://epublications.marquette.edu/chem_fac/1129