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

Ze-Kun Yang; Chao Wang; Masanobu Uchiyama

doi:10.1055/s-0036-1590863

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(19): 2565-2568
DOI: 10.1055/s-0036-1590863

cluster

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

Ze-Kun Yang

^aGraduate School of Pharmaceutical Sciences, the University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to 113-0033, Japan eMail: chaowang@mol.f.u-tokyo.ac.jp eMail: uchiyama@mol.f.u-tokyo.ac.jp

^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

,

Chao Wang*

^aGraduate School of Pharmaceutical Sciences, the University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to 113-0033, Japan eMail: chaowang@mol.f.u-tokyo.ac.jp eMail: uchiyama@mol.f.u-tokyo.ac.jp

^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

,

Masanobu Uchiyama*

^aGraduate School of Pharmaceutical Sciences, the University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to 113-0033, Japan eMail: chaowang@mol.f.u-tokyo.ac.jp eMail: uchiyama@mol.f.u-tokyo.ac.jp

^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

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Abstract

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Published as part of the Cluster C–O Activation

Abstract

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.

Key words

cross-coupling - C–O bond cleavage - nickel catalyst - organoaluminum - DFT calculation

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Referenzen

References and Notes
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