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Palladium-Catalyzed Three-Component Tandem Coupling–Carboannulation Reaction Leading to Polysubstituted [60]Fullerene-Fused Cyclopentanes

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journal contribution
posted on 17.12.2019, 14:37 by Qingfeng Liu, Tong-Xin Liu, Jinliang Ma, Guisheng Zhang
The first example of transition-metal catalyzed multicomponent carboannulation of [60]­fullerene has been developed. [60]­Fullerene, 2-(2,3-allenyl)­malonates, and (hetero)­aryl iodides undergo a Pd(0)-catalyzed tandem coupling–carboannulation process for regioselective access to novel polysubstituted [60]­fullerene-fused cyclopentane derivatives with a wide range of substrate scope and high functional group compatibility. A plausible mechanism involving the formation of a fullerene−π-allylpalladium complex with the characteristic of a fullerene cation as a key intermediate has been proposed.