Pd-catalyzed intramolecular addition of active methylene compounds to alkynes with subsequent cross-coupling with (hetero)aryl halides

被引：5

作者：

Blocka, Aleksandra ^{[1
]}

Woznicki, Pawel ^{[2
]}

Stankevic, Marek ^{[2
]}

Chaladaj, Wojciech ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

[2] Marie Curie Sklodowska Univ Lublin, Dept Organ Chem, Fac Chem, Gliniana 33, PL-20614 Lublin, Poland

来源：

RSC ADVANCES | 2019年 / 9卷 / 68期

关键词：

ALLYLIDENE CYCLOPENTANES; ORGANIC HALIDES; METAL; CARBOPALLADATION; CYCLIZATION; CARBOANNULATION; HETEROCYCLES; DERIVATIVES; INDENES; CASCADE;

D O I：

10.1039/c9ra08002c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report an efficient protocol for tandem Pd-catalyzed intramolecular addition of active methylene compounds to alkynes, followed by subsequent cross-coupling with (hetero)aryl bromides and chlorides. The reaction proceeds under mild conditions, providing excellent functional group tolerance, including unprotected OH, NH2 groups, enolizable ketones, or a variety of heterocycles. Mechanistic studies point towards a catalytic cycle involving oxidative addition, intramolecular nucleophilic addition to the Pd(ii)-activated alkyne, and reductive elimination, with 5-exo-dig cyclization being the rate limiting step.

引用

页码：40152 / 40167

页数：16

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