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Synthesis of gem-Difluorinated N-Boc Amines from N-Boc Imines via Difluorinated Phosphonium Salts
Gregory A Lozhkin1,2, Alexey L Trifonov1, Alexander D Dilman1
1N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky Prospekt 47, Russian Federation.
Abstract:
A one-pot metal-free protocol toward gem-difluorinated N-Boc-protected amines is described. At first, N-Boc imines react with in situ-generated phosphorus ylide, producing gem-difluorinated phosphonium salts, which subsequently behave as a source of difluoroalkyl radicals under photoredox conditions. The process works using a phenothiazine-type photocatalyst, Hantzsch ester, and electron-deficient alkenes. Facile removal of the Boc group from the products affords difluorinated primary amine hydrochlorides.
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