IrIII-Catalyzed Direct C-7 Amidation of Indolines with Sulfonyl, Acyl, and Aryl Azides at Room Temperature

被引：57

作者：

Hou, Wei ^{[1
]}

Yang, Yaxi ^{[1
]}

Ai, Wen ^{[2
,3
]}

Wu, Yunxiang ^{[1
]}

Wang, Xuan ^{[1
]}

Zhou, Bing ^{[1
]}

Li, Yuanchao ^{[1
]}

机构：

[1] Chinese Acad Sci, Dept Med Chem, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

[2] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[3] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Nitrogen heterocycles; C-H activation; Iridium; Regioselectivity; Amidation; C-H AMIDATION; BOND ALKYLATION; INDOLES; ARYLATION; ARENES; MILD; ACTIVATION; ALKENES; ALKENYLATION; ALKALOIDS;

D O I：

10.1002/ejoc.201403355

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general procedure for an Ir-III-catalyzed C-7 selective C-H amidation and amination of indolines is reported. The reaction exhibits good functional group tolerance, requires no external oxidants, and releases N-2 as the single byproduct, thus providing an environmentally benign, readily scalable method for the synthesis of 7-aminoindolines. More importantly, acyl, sulfonyl, and aryl azides can be employed as the amino source in this C-H amidation reaction under very mild and pH-neutral reaction conditions (i. e., room temperature) to afford N-(7-indolinyl) amides, N-(7indolinyl)-sulfonamides, and N-(7-indolinyl) arylamines in good to excellent yields. In addition, a one-pot synthesis for 7-aminoindoles was developed. Overall, this procedure is robust, reliable, and compatible in air.

引用

页码：395 / 400

页数：6

共 27 条

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