Copper-Catalyzed C(sp3)-H/C(sp3)-H Cross-Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2-Trifluoromethyl-Substituted Dihydropyrrol-2-ols

被引：71

作者：

Zhu, Chuanle ^{[1
,2
]}

Zhu, Rui ^{[1
]}

Zeng, Hao ^{[1
]}

Chen, Fulin ^{[1
]}

Liu, Chi ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Key Lab Funct Mol Engn Guangdong Prov, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

[2] South China Univ Technol, State Key Lab Pulp & Paper Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 43期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

C-H activation; copper catalysis; cross-dehydrogenative coupling; heterocycles; internal oxidants; C-H FUNCTIONALIZATION; OXIME ACETATES; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; CYCLIZATION; FLUORINE; STRATEGY; ACCESS; BONDS; BIDENTATE;

D O I：

10.1002/anie.201707719

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first oxidative C(sp(3))-H/C(sp(3))-H cross-dehydrogenative coupling (CDC) reaction promoted by an internal oxidant is reported. This copper-catalyzed CDC reaction of oxime acetates and trifluoromethyl ketones provides a simple and efficient approach towards 2-trifluoromethyldihydropyrrol-2-ol derivatives in a highly diastereoselective manner by cascade C(sp(3))-C(sp(3)) bond formation and cyclization. These products were further transformed into various significant and useful trifluoromethylated heterocyclic compounds, such as trifluoromethylated furan, thiophene, pyrrole, dihydropyridazine, and pyridazine derivatives. A trifluoromethylated analogue of an A beta(42) lowering agent was also synthesized smoothly. Preliminary mechanistic studies indicated that this reaction involves a copper(I)/copper(III) catalytic cycle with the oxime acetate acting as an internal oxidant.

引用

页码：13324 / 13328

页数：5

共 72 条

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