Rhodium(III)-catalyzed synthesis of indoles from 1-alkylidene-2-arylhydrazines and alkynes via C-H and N-N bond cleavages

被引：31

作者：

Matsuda, Takanori ^{[1
]}

Tomaru, Yuki ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 22期

关键词：

Alkyne; Annulation; C-H bond functionalization; Hydrazine; Indole; Rhodium; PALLADIUM-CATALYZED REACTIONS; INTERNAL ALKYNES; OXIDATIVE CYCLIZATION; EFFICIENT SYNTHESIS; DIRECTING GROUP; ARYL ENAMINES; ACTIVATION; FUNCTIONALIZATION; ISOQUINOLINES; ANILINES;

D O I：

10.1016/j.tetlet.2014.04.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Alkylidene-2-arylhydrazines undergo annulative coupling with internal alkynes in the presence of a rhodium(III) catalyst and a copper(II) salt. The reaction proceeds through cleavage of the C-H and N-N bonds of hydrazines to afford 1,2,3-trisubstituted indole derivatives. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3302 / 3304

页数：3

共 50 条

[31] SYNTHESIS OF PHENANTHRIDINES AND RELATED COMPOUNDS BY PALLADIUM-CATALYZED DIRECT COUPLING VIA C-H AND N-H BOND CLEAVAGES
Takeda, Daisuke
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
HETEROCYCLES, 2012, 86 (01) : 487 - 496
[32] Synthesis of indoles via palladium-catalyzed C-H activation of N-aryl amides followed by coupling with alkynes
Zhou, Feng
Han, Xiuling
Lu, Xiyan
TETRAHEDRON LETTERS, 2011, 52 (36) : 4681 - 4685
[33] Rhodium(III)-Catalyzed C-H Alkynylation of N-Methylsulfoximines
Wang, Tao
Wang, Yi-Ning
Wang, Rui
Wang, Xi-Sheng
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2449 - 2452
[34] Rhodium-Catalyzed Annulative Coupling of 3-Phenylthiophenes with Alkynes Involving Double C-H Bond Cleavages
Iitsuka, Tomonori
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) : 385 - 389
[35] A Synthesis of 1H-Indazoles via a Cu(OAc)2-Catalyzed N-N Bond Formation
Chen, Cheng-yi
Tang, Guangrong
He, Fengxian
Wang, Zhaobin
Jing, Hailin
Faessler, Roger
ORGANIC LETTERS, 2016, 18 (07) : 1690 - 1693
[36] Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides
Zhu, Chen
Falck, John R.
TETRAHEDRON, 2012, 68 (45) : 9192 - 9199
[37] DFT studies on rhodium(iii)-catalyzed synthesis of indanones from N-methoxybenzamides via C-H activation reaction
Li, Qianqian
Wei, Meiju
NEW JOURNAL OF CHEMISTRY, 2022, 46 (34) : 16576 - 16583
[38] Rhodium(III)-catalyzed allylic C-H bond amination. Synthesis of cyclic amines from ω-unsaturated N-sulfonylamines
Cochet, Thomas
Bellosta, Veronique
Roche, Didier
Ortholand, Jean-Yves
Greiner, Alfred
Cossy, Janine
CHEMICAL COMMUNICATIONS, 2012, 48 (87) : 10745 - 10747
[39] Annulation of Hydrazones and Alkynes via Rhodium(III)-Catalyzed Dual C-H Activation: Synthesis of Pyrrolopyridazines and Azolopyridazines
Streit, Andrew D.
Zoll, Adam J.
Hoang, Gia L.
Ellman, Jonathan A.
ORGANIC LETTERS, 2020, 22 (03) : 1217 - 1221
[40] Rhodium(iii)-catalyzed C-H activation/annulation of N-iminopyridinium ylides with alkynes and diazo compounds
Li, Xiang
Zhang, Ruihong
Qi, Yaoting
Zhao, Qing
Yao, Tuanli
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (06): : 1190 - 1196

← 1 2 3 4 5 →