Copper-Catalyzed Functionalizations of C60 with Amino Alcohols

Hai-Tao Yang, Jie Ge, Xin-Wei Lu, Xiao-Qiang Sun, Chun-Bao Miao

Index: 10.1021/acs.joc.7b00741

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Abstract

CuI-catalyzed diverse functionalizations of C60 with amino alcohols with aerobic oxygen as the sole oxidant have been explored. For 2-/3-amino alcohols, an aminooxygenation reaction occurs to generate fulleromorpholine and fullerooxazepane derivatives. When a tethered furan ring exists, a further intramolecular [4 + 2] reaction with the neighboring double bond occurs to furnish the cis-1 products. In the case of 4-/5-amino alcohols, methanofullerenes linking with cyclic amides are obtained through cyclic enamine intermediates.