jo5b02457_si_001.pdf (2.7 MB)
Iron-Catalyzed Divergent Tandem Radical Annulation of Aldehydes with Olefins toward Indolines and Dihydropyrans
journal contribution
posted on 2015-12-18, 00:00 authored by Leiyang Lv, Longying Qi, Qiaoxia Guo, Baojian Shen, Zhiping LiIron-catalyzed
divergent tandem radical annulations of aldehydes with olefins are
reported. The new strategy allows the rapid and efficient construction
of various multifunctionlized indolines (R = Ar) and dihydropyrans
(R = Me), which are significant skeletons in bioactive natural products
and pharmaceuticals. The substituents of tertiary amines play vital
roles to facilitate the desired transformation. Mechanistic studies
on indoline formation disclose that the homolytic cleavage of the
carbonyl C–H bond might be involved in the rate-determining
step, while dissociation of the aromatic C–H bond was most
likely included in the product-determining step.