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铑催化的α-重氮丙二酸酯与芳基 C-H 键的分子间卡宾官能团化反应。

Rh-catalyzed intermolecular carbenoid functionalization of aromatic C-H bonds by α-diazomalonates.

机构信息

State Key Laboratory for Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.

出版信息

J Am Chem Soc. 2012 Aug 22;134(33):13565-8. doi: 10.1021/ja305771y. Epub 2012 Aug 7.

DOI:10.1021/ja305771y
PMID:22860697
Abstract

A Rh-catalyzed intermolecular coupling of diazomalonates with arene C-H bonds is reported. The reaction is initiated by electrophilic C-H activation, which is followed by coupling of the arylrhodium(III) complex with the diazomalonate. In most cases, arenes with oximes, carboxylic acids, and amines as directing groups cross-couple with diazomalonates with excellent regioselectivities and functional group tolerance, and thus, this reaction offers a new route to α-aryl carbonyl compounds for specific applications.

摘要

报告了一种 Rh 催化的重氮戊二烯酸盐与芳环 C-H 键的分子间偶联反应。该反应由亲电 C-H 活化引发,随后芳基铑(III)配合物与重氮戊二烯酸盐偶联。在大多数情况下,带有肟、羧酸和胺的芳环与重氮戊二烯酸盐交叉偶联,具有极好的区域选择性和官能团耐受性,因此,该反应为特定应用提供了一种合成α-芳基羰基化合物的新途径。

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