Automated Nanomole-Scale Reaction Screening toward Benzoate Bioisosteres: A Photocatalyzed Approach to Highly Elaborated Bicyclo[1.1.1]Pentanes
James J. Mousseau, Matthew A. Perry, Mark W. Bundesmann, Gary M. Chinigo, Chulho Choi, Gary M. Gallego, Robert W. Hicklin, Susan Hoy, David C. Limburg, Neal W. Sach, Yuan Zhang
Abstract
Through the application of high-throughput nanoscale optimization, a mild, photocatalyzed, Minisci-like protocol was developed to access highly functionalized 1,3-disubstituted bicyclopentanes. The benzoate-isosteric compounds were prepared using a readily available organic photocatalyst, mitigating the need for precious metals. The strategy described furnished products in synthetically useful yields and was demonstrated to be executable in parallel medicinal chemistry format.
Topics & Concepts
CatalysisChemistryCombinatorial chemistryExecutablePhotocatalysisBicyclic moleculeOrganic chemistryComputer scienceOperating systemRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods