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

页码：701 / 708

页数：8

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