Iron-Catalyzed Divergent Tandem Radical Annulation
of Aldehydes with Olefins toward Indolines and Dihydropyrans
Leiyang Lv
Longying Qi
Qiaoxia Guo
Baojian Shen
Zhiping Li
10.1021/acs.joc.5b02457.s001
https://acs.figshare.com/articles/journal_contribution/Iron_Catalyzed_Divergent_Tandem_Radical_Annulation_of_Aldehydes_with_Olefins_toward_Indolines_and_Dihydropyrans/2097514
Iron-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.
2015-12-18 00:00:00
Indoline
skeleton
carbonyl
Aldehyde
Olefin
Mechanistic studies
pharmaceutical
homolytic cleavage
dissociation
olefins
annulation
strategy
role
aldehyde
construction
transformation
Ar
amines
substituent
tandem
dihydropyran
multifunctionlized indolines
Tandem Radical Annulation
indoline formation
bioactive
bond