A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity

被引：79

作者：

Bryan, Christopher S. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

基金：

加拿大自然科学与工程研究理事会;

关键词：

EFFICIENT SYNTHESIS; CYCLIZATION; DERIVATIVES; DOMINO; BOND; 1,1-DIBROMO-1-ALKENES; 1,1-DIBROMOOLEFINS; ARYLATION; ENEDIYNES; INDOLE;

D O I：

10.1021/ol100844v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction. The reaction is highly modular and proceeds under mild conditions. The choice of ligand was found to be crucial to control the selectivity of the reaction. Isolation of intermediates under different conditions provides insight into the mechanism.

引用

页码：2754 / 2757

页数：4

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