Amide C–N bonds activation by A new variant of bifunctional N-heterocyclic carbene

Yuxing Cai, Yuxin Zhao, Kai Tang, Hong Zhang, Xueling Mo, Jiean Chen () and Yong Huang ()
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Yuxing Cai: Peking University Shenzhen Graduate School
Yuxin Zhao: The Hong Kong University of Science and Technology, Clear Water Bay
Kai Tang: Shenzhen Bay Laboratory
Hong Zhang: Shenzhen Bay Laboratory
Xueling Mo: Shenzhen Bay Laboratory
Jiean Chen: Shenzhen Bay Laboratory
Yong Huang: The Hong Kong University of Science and Technology, Clear Water Bay

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract We report an organocatalyst that combines a triazolium N-heterocyclic carbene (NHC) with a squaramide as a hydrogen-bonding donor (HBD), which can effectively catalyze the atroposelective ring-opening of biaryl lactams via a unique amide C–N bond cleavage mode. The free carbene species attacks the amide carbonyl, forming an axially chiral acyl-azolium intermediate. Various axially chiral biaryl amines can be accessed by this methodology with up to 99% ee and 99% yield. By using mercaptan as a catalyst turnover agent, the resulting thioester synthon can be transformed into several interesting atropisomers. Both control experiments and theoretical calculations reveal the crucial role of the hybrid NHC-HBD skeleton, which activates the amide via H-bonding and brings it spatially close to the carbene centre. This discovery illustrates the potential of the NHC-HBD chimera and demonstrates a complementary strategy for amide bond activation and manipulation.

Date: 2024
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DOI: 10.1038/s41467-024-44756-8

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