Issue 20, 2019
From the journal:

Chemical Science

Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations†

Yi Yang, ORCID logo *a   Qinghai Zhou,b   Junjie Cai,a   Teng Xue,c   Yingle Liu,a   Yan Jiang,a   Yumei Su,a   Lungwa Chung ORCID logo *b  and  David A. Vicic*c  

* Corresponding authors

a Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, 180 Xueyuan Street, Huixing Lu, Zigong, Sichuan 643000, China
E-mail: yangyiyoung@163.com

b Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
E-mail: oscarchung@sustc.edu.cn

c Department of Chemistry, Lehigh University, 6 E. Packer Ave., Bethlehem, PA 18015, USA
E-mail: vicic@lehigh.edu

Abstract

We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickel-catalyzed Suzuki-type alkylation and fluoroalkylation coupling reactions. Compared with the [LnNiII(aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted precatalyst [(bipy)Ni(CH2CF3)2] with bench-top stability, good solubilities in organic media and interesting catalytic activities. Preliminary mechanistic studies reveal that an eliminative extrusion of a vinylidene difluoride (VDF, CH2[double bond, length as m-dash]CF2) mask from [(bipy)Ni(CH2CF3)2] is a critical step for the initiation of a catalytic reaction.

Graphical abstract: Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations

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Article information

DOI
https://doi.org/10.1039/C9SC00554D
Article type
Edge Article
Submitted
30 Jan 2019
Accepted
16 Apr 2019
First published
17 Apr 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 5275-5282

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Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations

Y. Yang, Q. Zhou, J. Cai, T. Xue, Y. Liu, Y. Jiang, Y. Su, L. Chung and D. A. Vicic, Chem. Sci., 2019, 10, 5275 DOI: 10.1039/C9SC00554D

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