Chemical functionalization of fullerenes has been an important topic in fullerene chemistry. Herein, an unprecedented Pd-catalyzed migration reaction of [60]fullerene with allyloxy-tethered aryl iodides is present for...Chemical functionalization of fullerenes has been an important topic in fullerene chemistry. Herein, an unprecedented Pd-catalyzed migration reaction of [60]fullerene with allyloxy-tethered aryl iodides is present for the preparation of novel [60]fullerene-fused allylbenzofurans. The use of 1,2-bis(diphenylphosphino)benzene (DPPBz) as a ligand is crucial for the success of the transformation. The reaction shows high chemo- and regioselectivity, and is flexible with regard to allyl-migration site, providing a new and efficient approach to rare [60]fullerene-fused benzofurans. Control experiments disclose that the reaction most probably undergoes a sequential C—O bond cleavage/allyl-migration/intermolecular cycloaddition cascade process.展开更多
基金grateful for financial support from the National Natural Science Foundation of China(U1904181 and 21877206)Zhongyuan Qianren Jihua(ZYQ201912132)the 111 Project(D17007)。
文摘Chemical functionalization of fullerenes has been an important topic in fullerene chemistry. Herein, an unprecedented Pd-catalyzed migration reaction of [60]fullerene with allyloxy-tethered aryl iodides is present for the preparation of novel [60]fullerene-fused allylbenzofurans. The use of 1,2-bis(diphenylphosphino)benzene (DPPBz) as a ligand is crucial for the success of the transformation. The reaction shows high chemo- and regioselectivity, and is flexible with regard to allyl-migration site, providing a new and efficient approach to rare [60]fullerene-fused benzofurans. Control experiments disclose that the reaction most probably undergoes a sequential C—O bond cleavage/allyl-migration/intermolecular cycloaddition cascade process.
