Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis.

Angew Chem Int Ed Engl

UCSD-CNRS Joint Research Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.

Published: February 2019

Primary aminoboranes (RNHBR ), 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.

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http://dx.doi.org/10.1002/anie.201814081DOI Listing

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