BT(S) Directing Group Preprint Online

In a pre-print appearing online today in ChemRxiv, Andrew, Kin, and Malkanthi describe the discovery and development of a benzothiazole sulfide, BT(S), directing group for use in catalytic alkene and C–H functionalization reactions catalyzed by palladium(II). The weakly coordinating nature of BT(S) makes it well-suited for reactions that rely on the directing group for selectivity control but also require conformational flexibility in key steps, such as the regioselective oxidative Heck arylation of 1,2-dialkylalkenes. The precursor compound, mercaptobenzothiazole is incredibly cheap (~$50/kg from MilliporeSigma), and the BT(S) can readily be converted to a BT sulfone for Julia olefination chemistry, among other transformations. Congrats to all of the authors, and thanks to Dr. Jason Chen from the Automated Synthesis Facility for guidance on Design of Experiment (DoE) optimization and kinetics runs. Click here for a link to the paper.