Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production,Beilstein Journal of Organic Chemistry

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Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C70 production
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2024-02-13 , DOI: 10.3762/bjoc.20.28
Cristina Castanyer , Anna Pla-Quintana , Anna Roglans , Albert Artigas , Miquel Solà

Abstract

The regioselective functionalization of fullerenes holds significant promise for applications in the fields of medicinal chemistry, materials science, and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions between diynes and C₇₀ as a novel procedure for generating C₇₀ bis(fulleroid) derivatives. The aim is to shed light on the regioselectivity of the process through both experimental and computational approaches. In addition, the photooxidation of one of the C–C double bonds in the synthesized bis(fulleroids) affords open-cage C₇₀ derivatives having a 12-membered ring opening.