Diborodichloromethane as Versatile Reagent for Chemodivergent Synthesis of gem‐Diborylalkanes

Abstract

AbstractThe 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 (B2pin2). 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 13C‐chloroform and 10B2pin2 enables the synthesis of isotopically enriched 13C‐DBDCM and 10B‐DBDCM reagents, which are beneficial for the convenient synthesis of carbon‐13 and boron‐10 molecules.