Susanna Kunz, Fredrik Barnå, Mauricio Posada Urrutia, Fredric J L Ingner, Andrea Martínez-Topete, Andreas Orthaber, Paul J Gates, Lukasz T Pilarski, Christine Dyrager
Despite growing interest in 2,1,3-benzothiadiazole (BTD) as an integral component of many functional molecules, methods for the functionalization of its benzenoid ring have remained limited, and many even simply decorated BTDs have required de novo synthesis. We show that regioselective Ir-catalyzed C-H borylation allows access to versatile 5-boryl or 4,6-diboryl BTD building blocks, which undergo functionalization at the C4, C5, C6, and C7 positions. The optimization and regioselectivity of C-H borylation are discussed...
April 22, 2024: Journal of Organic Chemistry