Forging sp3 Architectures via sp3 C−C Bond Cleavage and 1,2-Alkylboration Strategies

Identifier:  TDX:4176

Handle: https://hdl.handle.net/20.500.11797/TDX4176

Authors:  Cong, Fei

Abstract:
With the increasing demand for sp3 architectures in drug development, new methods to construct sp3-carbon linkages have attracted significant attention from medicinal chemists. Metal-catalyzed cross-coupling reactions have offered innovative solutions to synthesize structurally diverse sp3-carbon scaffolds. However, forging sp3 C–C bonds by transition metal-catalysis still leaves ample room for further improvements. On the one hand, while the majority of cross-coupling reactions focus on the activation of carbon-heteroatom bonds or C–H bonds, general strategies based on the functionalization of particularly strong C–C bonds still remain elusive. On the other hand, despite the advances realized in 1,2-carboboration of π‐systems, transition metal-catalyzed construction of C(sp3)–C(sp3) bonds with alkyl halides as the source of sp3-carbon centers is still challenging. To this end, we have developed new methods for the synthesis of sp3 architectures via C−C bond cleavage and Ni-catalyzed 1,2-alkylboration strategies, which offer a complementary new blueprint for preparing densely functionalized, yet synthetically versatile, sp3 C−C bonds from simple and readily accessible precursors.