Deprotonative Functionalization of the Difluoromethyl Group | Zendy

Laura L. Santos | Zendy; Armen Panossian | Zendy; Morgan Donnard | Zendy; JeanPierre Vors | Zendy; Sergii Pazenok | Zendy; David Bernier | Zendy; Frédéric R. Leroux | Zendy

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Deprotonative Functionalization of the Difluoromethyl Group

Author(s) -

Laura L. Santos,

Armen Panossian,

Morgan Donnard,

JeanPierre Vors,

Sergii Pazenok,

David Bernier,

Frédéric R. Leroux

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c03380

Subject(s) - deprotonation , chemistry , electrophile , surface modification , pyridine , fluoride , trapping , group (periodic table) , quenching (fluorescence) , medicinal chemistry , combinatorial chemistry , photochemistry , organic chemistry , catalysis , inorganic chemistry , ion , quantum mechanics , ecology , physics , fluorescence , biology

The functionalization of 3-(difluoromethyl)pyridine has been developed via direct deprotonation of -CHF 2 with a lithiated base and subsequent trapping with various electrophiles in THF. In situ quenching gives access to 3-pyridyl-CF 2 -SiMe 2 Ph as a new silylated compound, which can be postfunctionalized with a fluoride source to obtain a larger library of 3-(difluoroalkyl)pyridines that could not be accessed via direct deprotonation.

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