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Updated: Feb 12, 2026

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Published on: July 28, 2022
Rh(iii)-catalyzed regioselective intermolecular N-methylene Csp3-H bond carbenoid insertion
Haisheng Xie1, Zongren Ye2, Zhuofeng Ke2
1School of Chemistry and Chemical Engineering , South China University of Technology , No. 381 Wushan Road , Guangzhou , 510641 , P. R. China . Email: jianghf@scut.edu.cn ;
Abstract:
A Rh(iii)-catalyzed regioselective intermolecular carbenoid insertion into the N-methylene Csp3-H bond of acyclic aliphatic amides has been achieved, taking advantage of bidentate-chelation assistance. This methodology has been successfully applied to a broad range of linear and branched-chain N-alkylamides, thus providing a practical method for the assembly of diverse beta-amino esters. Mechanism studies and density functional theory (DFT) calculations revealed that a singlet Fischer type carbene insertion via an outer-sphere pathway was involved in this N-methylene Csp3-H bond carbenoid insertion.
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