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

Yang, Yi; Zhou, Qinghai; Cai, Junjie; Xue, Teng; Liu, Yingle; Jiang, Yan; Su, Yumei; Chung, Lungwa; Vicic, David A.

doi:10.1039/c9sc00554d

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

Journal Article · 17 April 2019 · Chemical Science

DOI: https://doi.org/10.1039/c9sc00554d · OSTI ID:1509518

^[1]; Zhou, Qinghai ^[2]; Cai, Junjie ^[1]; Xue, Teng ^[3]; Liu, Yingle ^[1]; Jiang, Yan ^[1]; Su, Yumei ^[1];

^[2]; Vicic, David A. ^[3]

Sichuan Univ .of Science & Engineering (China)
Southern Univ. of Science and Technology, Shenzhen (China)
Lehigh Univ., Bethlehem, PA (United States)

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 [L_nNi^II(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=CF₂) mask from [(bipy)Ni(CH₂CF₃)₂] is a critical step for the initiation of a catalytic reaction.

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Research Organization:: Lehigh Univ., Bethlehem, PA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC); Science & Technology Department of Sichuan Province; Key Laboratory of Vanadium and Titanium of Sichuan Province; Sichuan University of Science and Engineering

Grant/Contract Number:: SC0009363; 12502131; 21672096; 21702095; 2018JZ0061; 2018HH0128; 18CZ0024; 2108FTSZ03; 2017RCL03

OSTI ID:: 1509518

Alternate ID(s):: OSTI ID: 1611202; OSTI ID: 1696921

Journal Information:: Chemical Science, Vol. 10, Issue 20; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 11 works

Citation information provided by
Web of Science

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