4.8 Article

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

Journal

CHEMICAL SCIENCE
Volume 10, Issue 20, Pages 5275-5282

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc00554d

Keywords

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Funding

  1. National Natural Science Foundation of China [21502131, 21672096, 21702095]
  2. Science & Technology Department of Sichuan Province [2018JZ0061, 2018HH0128]
  3. Education Department of Sichuan Province [18CZ0024]
  4. Key Laboratory of Vanadium and Titanium of Sichuan Province [2018FTSZ03]
  5. Sichuan University of Science and Engineering [2017RCL03]
  6. Shenzhen Nobel Prize Scientists Laboratory Project [C17213101]
  7. Office of Basic Energy Sciences of the U.S. Department of Energy [DE-SC0009363]

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We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickelcatalyzed 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] CF2) mask from [(bipy) Ni(CH2CF3) (2)] is a critical step for the initiation of a catalytic reaction.

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