Dillon T. Flood; Shota Asai; Xuejing Zhang; Jie Wang; Leonard Yoon; Zoë C. Adams; Blythe C. Dillingham; Brittany Sanchez; Julien C. Vantourout; Mark E. Flanagan; David W. Piotrowski; Paul Richardson; Samantha Green; Ryan Shenvi; Jason Chen; Phil Baran; Philip Dawson
J. Am. Chem. Soc., 2019, 141, 25, 9998-10006
https://doi.org/10.1021/jacs.9b03774

Abstract

Herein, we present the adaptation of reversible adsorption to solid support (RASS) for a DEL setting, which allows reactions to be performed in organic solvents at near anhydrous conditions opening previously inaccessible chemical reactivities to DEL. The RASS approach enabled the rapid development of C(sp2)-C(sp3) decarboxylative cross-couplings with broad substrate scope, an electrochemical amination (the first electrochemical synthetic transformation performed in a DEL context), and improved reductive amination conditions. We believe that RASS will offer expedient access to new DEL reactivities, expanded chemical space, and ultimately more drug-like libraries.