Amines and carboxylic acids are abundant building blocks that are classically united through the amide coupling. The availability of new and complementary amine–acid coupling reactions would expand accessible chemical space. In addition to mapping these unexplored amine–acid couplings, we have been developing them into viable reaction methods using high throughput experimentation (HTE). Utilizing an HTE workflow and platform we established in 24-, 96-, 384, and 1,536-well plates, we have been discovering novel amine–acid coupling reactions. We have reported a new de-aminative amine–acid esterification that couples diverse carboxylic acids to diazonium salts derived from aryl amines. Through the continuous application of HTE techniques, we also identified additional amine–acid related transformations. We will present the establishment of a deconvolution analysis protocol to reveal unexpected reactivities in HTE campaigns, as well as the development of robust reaction methods.

Discovery and development of amine–carboxylic acid coupling reactions using high throughput experimentation

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.