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Iron‐catalyzed hydrosilylation of diacids in the presence of amines: a new route to cyclic amines
Author(s) -
Wei Duo,
Netkaew Chakkrit,
Wu Jiajun,
Darcel Christophe
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000881
Subject(s) - hydrosilylation , amine gas treating , chemistry , catalysis , cyclic amines , organic chemistry , solvent , hydride , alkylation , adipic acid , combinatorial chemistry , hydrogen
Cyclic amines (such as pyrrolidines, piperidines and azepanes) are present in a large class of natural products and bioactive molecules. Herein, we present a novel chemoselective strategy for building N ‐substituted cyclic amines via iron catalyzed one‐pot hydrosilylation starting from readily available dicarboxylic acids and amines, with hydrosilanes as the hydride sources. The described methodology allows the preparation of a wide range of N ‐alkylated and arylated cyclic amine derivatives (including pharmaceuticals Fenpiprane and Prozapine) in moderate to excellent yields, starting from inexpensive succinic, glutaric, and adipic acids with dimethyl carbonate as a green solvent.