Palladium-Catalyzed Construction of Spirooxindoles by Arylative Cyclization of 3-(γ,δ-Disubstituted)allylidene-2-Oxindoles

被引：35
|
作者：
Kim, Ko Hoon [1 ,2 ]
Moon, Hye Ran [1 ,2 ]
Lee, Junseong [1 ,2 ]
Kim, Jae Nyoung [1 ,2 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 04期
基金：
新加坡国家研究基金会;
关键词：
arylative cyclization; domino reactions; Fujiwara-Moritani reaction; palladium; spirooxindoles; BAYLIS-HILLMAN REACTION; C-H ACTIVATION; CRAFTS ALLYLIC ALKYLATION; EFFICIENT SYNTHESIS; SPIROCYCLIC OXINDOLES; ASYMMETRIC-SYNTHESIS; OXIDATIVE ARYLATION; STEREOSELECTIVE-SYNTHESIS; EXPEDIENT SYNTHESIS; ARENE INTERACTIONS;
D O I：
10.1002/adsc.201400965
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The palladium-catalyzed, one-pot arylative cyclization of 3-(gamma,delta-disubstituted) allylidene-2-oxindoles afforded spirodihydronaphthalene-2-oxindole frameworks via an oxidative Heck arylation (Fujiwara-Moritani reaction), an allylic palladium migration, and an aryl C-H bond functionalization/arylation cascade of reactions. This is a first example of the palladium-catalyzed oxidative arylation and an aryl C-H bond functionalization/arylation cascade reaction which involves an electrophilic arylative quenching of a pi-allylpalladium intermediate and a regio-controlled aryl C-H bond activation assisted by a weak palladium-arene interaction. Keywords: arylative cyclization; domino reactions;
引用
收藏
页码：701 / 708
页数：8
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