Sequential Phosphine-Catalyzed, Nucleophilic Thiol-Ene/Radical-Mediated Thiol-Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials

Authors

Justin W. Chan, University of Southern Mississippi
Charles E. Hoyle, University of Southern MississippiFollow
Andrew B. Lowe, University of Southern Mississippi

Document Type

Article

Publication Date

4-29-2009

Department

Polymers and High Performance Materials

Abstract

The first example of highly efficient sequential thiol-ene/thiol-yne reactions conducted in an orthogonal manner is presented and its broad application in the synthesis of polyfunctional materials demonstrated. The anionic chain mechanism of the phosphine-mediated thiol-ene reaction is highlighted, as is the radical-mediated thiol-yne reaction. Kinetic data for a model reaction are presented, followed by a discussion of the synthesis of a range of materials with diverse functionality, including an example of potential biomedical significance.

Publication Title

Journal of the American Chemical Society

Volume

131

Issue

16

First Page

5751

Last Page

5753

Recommended Citation

Chan, J. W., Hoyle, C. E., Lowe, A. B. (2009). Sequential Phosphine-Catalyzed, Nucleophilic Thiol-Ene/Radical-Mediated Thiol-Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials. Journal of the American Chemical Society, 131(16), 5751-5753.
Available at: https://aquila.usm.edu/fac_pubs/1312