A new and efficient synthesis of 2-substituted indenes has been achieved via palladium-catalyzed carboannulation of propargylic carbonates with nucleophiles in good to excellent yields. A variety of nucleophiles were tolerated in this reaction.
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Catalytic System-Controlled Regioselective 1,2- and 1,4-Carboannulations of [60]Fullerene.
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Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Selective functionalization of fullerenes is an important but challenging topic in fullerene chemistry and synthetic chemistry. Here we present the first example of catalytic system-controlled regioselective 1,2- and 1,4-addition reactions for the flexible and efficient synthesis of novel 1,2- and 1,4-carbocycle-fused fullerenes via a palladium-catalyzed decarboxylative carboannulation process.
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Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering , Henan Normal University, Xinxiang , Henan 453007 , China.
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.
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Department of Chemistry, Jadavpur University, Kolkata 700032, West Bengal, India.
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Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China.
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