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Consecutive β,β′‐Selective C(sp 3 )−H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C 6 F 5 ) 3
Author(s) -
Fang Huaquan,
Xie Kaixue,
Kemper Sebastian,
Oestreich Martin
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202016664
Subject(s) - silylation , chemistry , dehydrogenation , borane , medicinal chemistry , electrophile , catalysis , intramolecular force , alkyl , enamine , tertiary amine , amine gas treating , organic chemistry
Abstract Tris(pentafluorophenyl)borane has been found to catalyze the two‐fold C(sp 3 )−H silylation of various trialkylamine derivatives with dihydrosilanes, furnishing the corresponding 4‐silapiperidines in decent yields. The multi‐step reaction cascade involves amine‐to‐enamine dehydrogenation at two alkyl residues and two electrophilic silylation reactions of those enamines, one inter‐ and one intramolecular.