Issue 8, 2022

Photoredox/nickel dual catalyzed stereospecific synthesis of distal alkenyl ketones

Abstract

The selective C–C bond deconstruction/refunctionalization via a photoredox/nickel dual-catalyzed hydroalkylation of alkynes is developed under mild reaction conditions. In this protocol, a broad range of alkyl- and aryl-alkynes could react smoothly with cycloalkanols, affording the corresponding distal and site-specific vinyl-substituted ketones with high yields and excellent regioselectivities. Moreover, DFT calculations verified that the electron-rich behavior of aromatics and weak Brønsted bases have a common effect on the photocatalytic oxidant ring-opening of cyclobutanols.

Graphical abstract: Photoredox/nickel dual catalyzed stereospecific synthesis of distal alkenyl ketones

Supplementary files

Article information

Article type
Communication
Submitted
23 Nov 2021
Accepted
20 Dec 2021
First published
20 Dec 2021

Chem. Commun., 2022,58, 1171-1174

Photoredox/nickel dual catalyzed stereospecific synthesis of distal alkenyl ketones

T. Zhao, W. Yu, Z. Feng, H. Qin, H. Zheng and P. Xu, Chem. Commun., 2022, 58, 1171 DOI: 10.1039/D1CC06566A

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