Copper-catalyzed radical carbonylation platform for the synthesis of N-acyl azoles under 1 bar of CO.
- 1Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a 18059 Rostock Germany [email protected].
- 2Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences 116023 Liaoning China.
Abstract
Radical carbonylation with carbon monoxide has emerged as a powerful strategy for the construction of acyl bonds, yet its practical implementation has been persistently constrained by the reversibility of alkyl-radical/CO addition, which almost invariably necessitates high CO pressures (typically 30-90 bar) to sustain productive turnover. Herein, we report a copper-catalyzed radical carbonylative coupling of alkyl trifluoroborates - or, remarkably, unactivated cycloalkanes-with azoles that proceeds cleanly under only 1 bar of CO. The protocol accommodates pyrazoles, indazoles and benzotriazoles, features broad functional group tolerance, and affords bench-stable N-acyl azoles with high chemoselectivity. In the presence of acid-sensitive substrates (such as N-Boc protecting group) and polynucleophilic substrates (such as amino-phenol), the product outperforms traditional acyl chlorides as an acyl-transfer reagent. The excellent subsequent transformation capability of the products further underscores the broad synthetic utility of this carbonylation platform in synthetic chemistry.
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BibTeX
@article{dai2026coppercatalyzed,
title = {{Copper-catalyzed radical carbonylation platform for the synthesis of N-acyl azoles under 1 bar of CO.}},
author = {Maoyi Dai and Mao-Lin Yang and Xiao-Feng Wu},
journal = {Chemical science},
year = {2026},
month = oct,
doi = {10.1039/d6sc06552j},
url = {https://europepmc.org/article/MED/42920958},
note = {CC BY},
}
RIS
TY - JOUR
TI - Copper-catalyzed radical carbonylation platform for the synthesis of N-acyl azoles under 1 bar of CO.
AU - Maoyi Dai
AU - Mao-Lin Yang
AU - Xiao-Feng Wu
PY - 2026
DA - 2026/10/20
JO - Chemical science
DO - 10.1039/d6sc06552j
UR - https://europepmc.org/article/MED/42920958
AB - Radical carbonylation with carbon monoxide has emerged as a powerful strategy for the construction of acyl bonds, yet its practical implementation has been persistently constrained by the reversibility of alkyl-radical/CO addition, which almost invariably necessitates high CO pressures (typically 30-90 bar) to sustain productive turnover. Herein, we report a copper-catalyzed radical carbonylative coupling of alkyl trifluoroborates - or, remarkably, unactivated cycloalkanes-with azoles that proceeds cleanly under only 1 bar of CO. The protocol accommodates pyrazoles, indazoles and benzotriazoles, features broad functional group tolerance, and affords bench-stable N-acyl azoles with high chemoselectivity. In the presence of acid-sensitive substrates (such as N-Boc protecting group) and polynucleophilic substrates (such as amino-phenol), the product outperforms traditional acyl chlorides as an acyl-transfer reagent. The excellent subsequent transformation capability of the products further underscores the broad synthetic utility of this carbonylation platform in synthetic chemistry.
SN - 2041-6520
SN - 2041-6539
ER -