Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts

Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts

Shirong Lu, Weili Si, Ming Bao, Yoshinori Yamamoto, and Tienan Jin

WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University, Sendai 980-8577, Japan, and State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, China

Org. Lett., Article ASAP

Publication Date (Web): July 23, 2013 (Letter)

DOI: 10.1021/ol401876n

http://pubs.acs.org/doi/abs/10.1021/ol401876n

An efficient and highly selective Co-catalyzed radical cycloaddition of [60]fullerene with active dibromides for the synthesis of three-, five-, six-, and seven-membered carbocycle-fused fullerene monoadducts has been reported. The controlled experiments unambiguously disclosed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate.

Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts

Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts

Shirong Lu, Weili Si, Ming Bao, Yoshinori Yamamoto, and Tienan Jin

WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University, Sendai 980-8577, Japan, and State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, China

Org. Lett., Article ASAP

Publication Date (Web): July 23, 2013 (Letter)

DOI: 10.1021/ol401876n

http://pubs.acs.org/doi/abs/10.1021/ol401876n

An efficient and highly selective Co-catalyzed radical cycloaddition of [60]fullerene with active dibromides for the synthesis of three-, five-, six-, and seven-membered carbocycle-fused fullerene monoadducts has been reported. The controlled experiments unambiguously disclosed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate.