New ways to unite amines and carboxylic acids that complement the popular amide coupling significantly expand accessible chemical space. We have developed an amine–acid esterification based on pyridinium salt activation of C–N bonds. The reaction makes use of simple reagents and is readily applied to a wide variety of complex molecules including natural products and drug molecules. To fully realize the scope of this transformation, we developed an automated platform to run 96 well high-throughput experimentation plates and used it to generate a library of late-stage amlodipine derivatives. Results of this screen further demonstrate the applicability of this reaction to complex carboxylic acids as well as other nucleophiles.

Development and automation of a deaminative esterification reaction

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.