CO2-promoted photocatalytic aryl migration from nitrogen to carbon for switchable transformation of N-arylpropiolamides

Ge Liu, Denghui Ma, Jianchen Zhang, Fanyuanhang Yang, Yuzhen Gao () and Weiping Su ()
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Ge Liu: Chinese Academy of Sciences
Denghui Ma: Ningbo University of Technology
Jianchen Zhang: Chinese Academy of Sciences
Fanyuanhang Yang: Chinese Academy of Sciences
Yuzhen Gao: Chinese Academy of Sciences
Weiping Su: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Photocatalytic N-to-C aryl migration allows for quick construction of highly useful amide derivatives from readily available compounds. By developing the reactions of sodium sulfinates with the N-aryl-propiolamides, we herein demonstrate that the CO2-promoted visible-light-induced method enables a large variety of aryl groups on nitrogen atoms of the N-arylamides to undergo efficient aryl migration from N atom to C atom to synthesize tetra- and tri-substituted alkenyl amides selectively. 1,4-N-to-C aryl migration is a key step in this transformation which is achieved through photocatalytic radical-polar crossover pathway. The protocol exhibits the remarkably tolerant of the electronic properties of the migrating aryl substituent, as both electron-rich and -poor arenes are compatible with the migration process. As a result, this protocol features with a broad substrate scope, as demonstrated by more than 90 examples including complex bioactive compounds. Notably, abundant, nontoxic and low-cost CO2 acted as an essential and irreplaceable additive to enable the tetra- and tri-substituted alkenyl amides to be synthesized with excellent selectivity.

Date: 2024
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DOI: 10.1038/s41467-024-54239-5

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