Copper-Catalyzed Reaction of α-Aryldiazoesters with Terminal Alkynes: A Formal [3+2] Cycloaddition Route Leading to Indene Derivatives

被引：85
|
作者：
Park, Eun Ju
Kim, Seok Hwan
Chang, Sukbok [1 ]
机构：
[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 51期
关键词：
D O I：
10.1021/ja808080h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
It was discovered that Cu(lPr)Cl-catalyzed reaction of terminal alkynes with alpha-aryldiazoacetates provides indene derivatives, formal [3 + 2] cycloaddition adducts. Excellent regio- and chemoselectivity were observed to afford either 3H- or 1 H-indene esters depending on the reaction conditions employed. The reaction is proposed to proceed via tandem processes: alkyne insertion into copper-carbenoid, intramolecular electrophilic attack on the aromatic ring, and then isomerization.
引用
收藏
页码：17268 / +
页数：3
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