DOI: 10.1055/s-0036-1590863
© Georg Thieme Verlag Stuttgart · New York

DFT Studies Provide Mechanistic Insight into Nickel-Catalyzed Cross-Coupling Involving Organoaluminum-Mediated C–O Bond Cleavage

Ze-Kun Yanga, b, Chao Wang*a, b, Masanobu Uchiyama*a, b
  • aGraduate School of Pharmaceutical Sciences, the University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to 113-0033, Japan   Email:   Email:
  • bAdvanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory RIKEN, 2-1 Hirosawa, Wako-shi, Saitama-ken 351-0198, Japan
This work was supported by JSPS KAKENHI (S) (No. 24229011, No. 17H06173) (to M. U.). This research was also partly supported by grants from Asahi Glass Foundation, Nagase Science Technology Development Foundation, Sumitomo Foundation, and Kobayashi International Scholarship Foundation (to M. U.), and from YakuGaku ShinKoKai Foundation (to C. W.)
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Publication History

Received: 31 May 2017

Accepted after revision: 10 July 2017

Publication Date:
25 August 2017 (eFirst)

Published as part of the Cluster C–O Activation


Density functional theory (DFT) calculations were performed to examine the reaction pathway of Ni-catalyzed cross-coupling with organoaluminum through C–O bond cleavage. The results indicate that the strong Lewis acidity of organoaluminums significantly facilitates the transmetalation step, but not the oxidative addition or reductive elimination step.

Supporting Information