The dihalogenative cyclization of 1,6-enyne with the assistance of PhI(OAc)2 and lithium halide is presented. A plausible radical mechanism is proposed, which consists of addition of halogen radical to alkene, 5-exo-dig radical cyclization of enyne and halogenation via radical coupling. The alkenyl- and alkyl-halide groups in the resulted pyrrolidine products have been demonstrated to be facile handles for further transformations.
Ming Dong, Danfeng Wang, Xiaofeng Tong. PhI(OAc)2-Mediated Dihalogenative Cyclization of 1,6-Enyne with Lithium Halide. Organic letters. 2021 May 07;23(9):3588-3592
PMID: 33899488
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