CuI-catalyzed highly regioselective C-H functionalization of indoles using indole-3-tosylhydrazones as carbene precursor: An efficient synthesis of 3,3-bis(indolyl)methane derivatives

被引：16

作者：

Kamboj, Priya ^{[1
]}

Dutt, Sunil ^{[1
]}

Chakroborty, Sourav ^{[2
]}

Tyagi, Vikas ^{[1
]}

机构：

[1] Thapar Inst Engn & Technol, Sch Chem & Biochem, Patiala 147004, Punjab, India

[2] Univ Strasbourg, Inst Sci & Supramol Engn, CNRS, UMR 7006, 8 Rue Gaspard Monge, F-67000 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 43期

关键词：

Bis indoles; N-tosylhydrazone; Copper-catalyst; Regioselective; Carbene insertion; BIS; BIS(INDOLYL)METHANES; TOSYLHYDRAZONES; ALKYLATION;

D O I：

10.1016/j.tetlet.2019.151162

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we have developed a novel approach for synthesizing symmetrical and unsymmetrical 3,3-bis (indolyl)methane derivatives via Cul-catalyzed C-H functionalization of indole using indole-3-tosylhydrazones as carbene precursor. This procedure works well with different substitutions such as NO2, Br, CH3 and OMe on indole or indole-3-tosylhydrazones and features high regioselectivity for C-3 functionalization over the C-1 and N-1 positions. Further, we have also revealed the feasibility of this protocol in a one-pot fashion starting from indole-3-carboxyaldehyde. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：6

共 2 条

[1] Regioselective synthesis of 3,3-bis(indolyl)propanoic acid derivatives by iron(III)-catalyzed hydroarylation of propynoic acid derivatives with indoles
Kutubi, Md. Shahajahan
Kitamura, Tsugio
TETRAHEDRON, 2011, 67 (42) : 8140 - 8145
[2] Bromine/para-Toluenesulfonic Acid-Catalyzed Synthesis of 3,3-Bis(indole-3-yl)indoline-2-(1H)-ones by Condensing Indoles with Isatins
Huang, Wenzhong
Nang, Lingli
Li, Xiangguang
Yuan, Lin
Ma, Yinhai
Liang, Deqiang
CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (10) : 1167 - 1172

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