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From Amines to Alkynes – Lighting the Way

preprint
submitted on 13.06.2018 and posted on 14.06.2018 by Dorota Gryko, Michał Ociepa, Joanna Turkowska
We present a metal-free photoredox strategy for the formation of Csp3-Csp bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridiniu salts with alkynyl tosylates, leading to functionalized alkynes , is easily scalable, offers broad substrate scope, high chemoselectivity, and mild conditions. Its potentials also highlighted by diversification of complex molecular scaffolds. Moreover, mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary, secondary and alkyl pyridinium salts.

Funding

National Science Center (PL) Grant no. 2016/21/BST5/03169 OPUS

History

Email Address of Submitting Author

dorota.gryko@icho.edu.pl

Email Address(es) for Other Author(s)

michalpio@wp.pl turkowska.j@gmail.com

Institution

Institute of Organic Chemistry Polish Academy of Sciences

Country

Poland

ORCID For Submitting Author

0000-0002-5197-4222

Declaration of Conflict of Interest

Authors declare no conflcit

Version Notes

first version

Exports