Nickel–Mediated Trifluoromethylation of Phenol Derivatives by Aryl C–O Bond Activation

Hu, Wei‐Qiang; Pan, Shen; Xu, Xiu‐Hua; Vicic, David A.; Qing, Feng‐Ling

doi:10.1002/anie.202004116

Nickel–Mediated Trifluoromethylation of Phenol Derivatives by Aryl C–O Bond Activation

Journal Article · Mon May 25 00:00:00 UTC 2020 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.202004116· OSTI ID:1696958

Hu, Wei‐Qiang ^[1]; Pan, Shen ^[2]; Xu, Xiu‐Hua ^[2]; Vicic, David A. ^[3]; ^[2]

Chinese Academy of Sciences, Shanghai (China); Lehigh University
Chinese Academy of Sciences, Shanghai (China)
Lehigh Univ., Bethlehem, PA (United States)

The increasing pharmaceutical importance of trifluoromethylarenes has stimulated the development of more efficient trifluoromethylation reactions. Tremendous efforts have focused on copper– and palladium–mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel–mediated trifluoromethylation of phenol derivatives with readily available trimethyl(trifluoromethyl)silane (TMSCF₃). The strategy relies on PMe₃–promoted oxidative addition and transmetalation, and CCl₃CN–induced reductive elimination. Here, the broad utility of this transformation has been demonstrated through the direct incorporation of trifluoromethyl into aromatic and heteroaromatic systems, including biorelevant compounds.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0009363

OSTI ID:: 1696958

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Vol. 59; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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