Issue 1, 2024

Nickel-catalyzed dynamic kinetic cross-electrophile coupling of benzylic alcohols and alkenyl triflates

Abstract

The direct deoxy-functionalization of alcohols through cross-coupling is synthetically appealing but remains a challenging task. In this manuscript, we report a dynamic kinetic cross-electrophile coupling reaction between benzylic alcohols and alkenyl triflates. This mild reaction enables the replacement of the alcohol group with an alkenyl functionality, yielding versatile benzyl-substituted cyclic alkenes. The production of cyclic alkenes makes the method orthogonal to the existing reductive coupling methodologies, which are mainly effective in producing acyclic derivatives. Functional groups such as ester, phenol, indole, heterocycle, and boronic ester are tolerated.

Graphical abstract: Nickel-catalyzed dynamic kinetic cross-electrophile coupling of benzylic alcohols and alkenyl triflates

Supplementary files

Article information

Article type
Research Article
Submitted
01 Sep 2023
Accepted
11 Nov 2023
First published
14 Nov 2023

Org. Chem. Front., 2024,11, 94-99

Nickel-catalyzed dynamic kinetic cross-electrophile coupling of benzylic alcohols and alkenyl triflates

X. Peng, J. Huang, G. Han and X. Shu, Org. Chem. Front., 2024, 11, 94 DOI: 10.1039/D3QO01416A

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