Issue 39, 2022

Visible light-driven carbamoyloxylation of the α-C(sp3)–H bond of arylacetones via radical-initiated hydrogen atom transfer

Abstract

Photocatalytic synthesis has emerged as an efficient route to transform CO2 into functionalized organic carbamates by photocatalysis. Herein, a catalyst-free carbamoyloxylation of arylacetones with CO2 and amines under visible light was developed for the synthesis of O-β-oxoalkyl carbamates in yields up to 93%. This protocol proceeded smoothly with the assistance of inexpensive carbon tetrabromide at room temperature under atmospheric CO2 pressure, leading to simultaneous construction of C–O and C–N bonds. Mechanism studies suggested the photoinduced hydrogen atom transfer (HAT) pathway followed by radical addition or single electron transfer (SET).

Graphical abstract: Visible light-driven carbamoyloxylation of the α-C(sp3)–H bond of arylacetones via radical-initiated hydrogen atom transfer

Supplementary files

Article information

Article type
Communication
Submitted
28 Mar 2022
Accepted
14 Apr 2022
First published
18 Apr 2022

Chem. Commun., 2022,58, 5845-5848

Visible light-driven carbamoyloxylation of the α-C(sp3)–H bond of arylacetones via radical-initiated hydrogen atom transfer

X. He, X. Yao, S. Cai, H. Li and L. He, Chem. Commun., 2022, 58, 5845 DOI: 10.1039/D2CC01761J

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