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铑(III)催化[2,2'-联吡啶]-6-甲酰胺与叶立德的区域选择性C3-H酰基甲基化反应

Rhodium(III)-Catalyzed Regioselective C3-H Acylmethylation of [2,2'-Bipyridine]-6-carboxamides with Sulfoxonium Ylides.

作者信息

Yu Jia, Wen Si, Ba Dan, Lv Weiwei, Chen Yanhui, Cheng Guolin

机构信息

School of Medicine, College of Materials Science & Engineering , Huaqiao University , Xiamen 361021 , China.

出版信息

Org Lett. 2019 Aug 16;21(16):6366-6369. doi: 10.1021/acs.orglett.9b02253. Epub 2019 Jul 30.

Abstract

A rhodium(III)-catalyzed C-H acylmethylation of tridentate [2,2'-bipyridine]-6-carboxamides was developed. A variety of [2,2'-bipyridine]-6-carboxamides could be monoalkylated exclusively at the C3 position with sulfoxonium ylides as carbene precursors, giving 3-alkylated products in high yields. This protocol proceeds through a rollover cyclometalation pathway, has a broad range scope of substrates, and exhibits excellent functional group tolerance.

摘要

开发了一种铑(III)催化的三齿[2,2'-联吡啶]-6-羧酰胺的C-H酰甲基化反应。以锍叶立德作为卡宾前体,多种[2,2'-联吡啶]-6-羧酰胺可以在C3位置专一性地进行单烷基化反应,以高产率得到3-烷基化产物。该反应通过翻转环金属化途径进行,底物范围广泛,并且对官能团具有出色的耐受性。

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