Overlooked potential of N,N-bidentate directing-groups in Ni-catalyzed C–H functionalization of benzamides.

Weirong Wu, Xufang Zhao, Guan Cheng, Lingjun Liu, Yulin Li, Tao Chen, Tony James, Yuxia Liu

Research output: Contribution to journalArticlepeer-review

Abstract

The Ni-catalyzed reactions of benzamides with bicyclic alkenes were explored using DFT calculations. An unprecedented “N-H deprotonation circumvented” catalytic mechanism was proposed, over the more common N-H/C-H activation mechanism, in which (i) the circumvention of N-H deprotonation ensures the presence of N-H⋯O hydrogen bond interaction, thereby stabilizing the critical ortho-C-H functionalization TS; and (ii) the N-H moiety retention results in a weak N⋯Ni σ-coordination, which is flexible to the configurational conversion during the key alkene insertion. These overlooked aspects of the functionalized N,N-bidentate directing groups will aid the design of new related catalytic reactions.

Original languageEnglish
Pages (from-to)482-485
Number of pages4
JournalChemical Communications
Volume59
Issue number4
Early online date19 Dec 2022
DOIs
Publication statusPublished - 19 Dec 2022

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