Issue 76, 2019

Ni-Catalyzed deaminative hydroalkylation of internal alkynes

Abstract

A regioselective cis-hydroalkylation of internal alkynes with readily prepared Katritzky pyridinium salts for the synthesis of tri-substituted alkenes is described. This reaction is the first example of a metal-catalyzed hydroalkylation of an alkyne via C–N bond activation of an amine. The reaction demonstrates broad scope and functional group tolerance, allowing access to desired products with high diversity. Preliminary mechanistic studies indicate that a combination of an SET-initiated radical process and Ni-catalyzed alkylation could engage in the reaction, which makes it possible to bypass the traditional open-shell addition pathway.

Graphical abstract: Ni-Catalyzed deaminative hydroalkylation of internal alkynes

Supplementary files

Article information

Article type
Communication
Submitted
13 Jul 2019
Accepted
30 Ago 2019
First published
30 Ago 2019

Chem. Commun., 2019,55, 11478-11481

Ni-Catalyzed deaminative hydroalkylation of internal alkynes

Z. Zhu, J. Tu and F. Liu, Chem. Commun., 2019, 55, 11478 DOI: 10.1039/C9CC05385A

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