Nickel-Catalyzed Quinoline Synthesis through Skeletal Editing Strategy Using Calcium Carbide as an Inorganic C2 Source
Zhiqiang Wang, Wei Chen, Jinhui Yang, Zheng Li
Abstract
High Resolution Image Download MS PowerPoint Slide Benzo[ c ]isoxazoles serve as versatile precursors for the skeletal editing of heterocyclic frameworks, wherein calcium carbide, as an inorganic C2 source, participates in C–O/N–O bond cleavage and concurrent C–C/C–N bond formation through molecular surgery. Diverse 3-substituted quinolines and 3,4-disubstituted quinolines were efficiently obtained via nickel-catalyzed one-pot three-component reactions using inexpensive, easy-to-handle solid calcium carbide as a substitute for flammable and explosive gaseous acetylene, and benzo[ c ]isoxazoles and organic boronic acids as commercially available starting materials. This strategy exhibits a broad substrate scope, high efficiency, simple workup procedures, and gram-scale applicability. These advantages underscore the unique role of calcium carbide in enabling skeletal editing for streamlined synthesis.