Diborodichloromethane as Versatile Reagent for Chemodivergent Synthesis of gem-Diborylalkanes

The development of boron reagents is crucial for synthetic chemistry. Herein, we present a scalable and practical synthesis of diborodichloromethane (DBDCM) through the reaction of trichloromethyllithium with bis(pinacolato)diboron (B(2)pin(2)). The resulting DBDCM reagent serves as a basic synthetic unit for the construction of various structurally diverse gem-diborylalkanes through controllable C-Cl functionalizations. Moreover, we have developed consecutive tetra-functionalizations of DBDCM for the construction of diverse tertiary and quaternary carbon containing molecules. The use of isotopically enriched C-13-chloroform and (10)B(2)pin(2) enables the synthesis of isotopically enriched C-13-DBDCM and B-10-DBDCM reagents, which are beneficial for the convenient synthesis of carbon-13 and boron-10 molecules.