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

1 Citation (SciVal)


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
Issue number4
Early online date19 Dec 2022
Publication statusPublished - 19 Dec 2022

Bibliographical note

National Natural Science Foundation of China
Fundref 501100001809
Natural Science Foundation of Shaanxi Province
Fundref 501100007128
Royal Society
Fundref 501100000288
Henan Normal University
Fundref 100009555
Wolfson Research Merit Award2020ZD01


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