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Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis
Author(s) -
Junor Glen P.,
Romero Erik A.,
Chen Xi,
Jazzar Rodolphe,
Bertrand Guy
Publication year - 2019
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.201814081
Subject(s) - aldimine , reagent , chemistry , combinatorial chemistry , organic chemistry , catalysis
Primary aminoboranes (RNHBR 2 ), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one‐pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods.