Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

被引：69

作者：

Biswas, Nandita ^{[1
]}

Sharma, Rahul ^{[1
]}

Srimani, Dipankar ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 14期

关键词：

Ruthenium; homogeneous catalysis; tridentate ligands; alkylation; borrowing hydrogen; indole; ONE-POT SYNTHESIS; BORROWING HYDROGEN; TRYPTAMINE DERIVATIVES; SUSTAINABLE SYNTHESIS; REDOX CONDENSATION; O-NITROANILINES; AMINO-ALCOHOLS; METHANOL; DEHYDROGENATION; TRANSITION;

D O I：

10.1002/adsc.202000326

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via "borrowing hydrogen" strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives.

引用

页码：2902 / 2910

页数：9

共 50 条

[31] Fe(II)-Catalyzed Metal-Ligand Cooperative Approach for Selective C3 -Alkylation of Indoles
Chakrabortya, Subhajit
Mandal, Sutanuva
Paul, Nanda D.
SYNLETT, 2024, 35 (20) : 2508 - 2514
[32] Ruthenium-catalyzed synthesis of indoles from anilines and trialkanolammonium chlorides in an aqueous medium
Cho, CS
Kim, JH
Shim, SC
TETRAHEDRON LETTERS, 2000, 41 (11) : 1811 - 1814
[33] First Example of C-3 Alkylation of Indoles with Activated Azetidines Catalyzed by Indium(III) Bromide
Yadav, J. S.
Reddy, B. V. Subba
Narasimhulu, G.
Satheesh, G.
SYNLETT, 2009, (05) : 727 - 730
[34] A highly regioselective C-3 benzylation reaction of indoles with alcohols catalysed by an N-heterocyclic carbene
Zhu, Yan-Fang
Lu, Guo-Ping
Cai, Chun
JOURNAL OF CHEMICAL RESEARCH, 2015, (08) : 438 - 441
[35] Ruthenium(II)-Catalyzed C-H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate-Controlled Synthesis of Indoles and 3H-Indoles
Li, Yunyun
Qi, Zisong
Wang, He
Yang, Xifa
Li, Xingwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 11877 - 11881
[36] Computational Insight into the Mechanism of Selective Imine Formation from Alcohol and Amine Catalyzed by the Ruthenium(II)-PNP Pincer Complex
Li, Haixia
Wang, Xiaotai
Wen, Mingwei
Wang, Zhi-Xiang
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (31) : 5011 - 5020
[37] Ruthenium-catalyzed synthesis of arylethyl 1,3,5-triazines from arylallyl alcohols and biguanides
Zeng, Ming
Xie, Zhong Pao
Cui, Dong-Mei
Zhang, Chen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (33) : 6140 - 6145
[38] The preparation of N-containing functionalized porous organic polymers for selective synthesis of C3-alkylated indoles and triazine derivatives
Zhang, Bo
Wang, Likui
Wang, Dawei
Zeng, Wei
NEW JOURNAL OF CHEMISTRY, 2022, 46 (47) : 22797 - 22803
[39] Selective Room-Temperature Hydrogenation of Amides to Amines and Alcohols Catalyzed by a Ruthenium Pincer Complex and Mechanistic Insight
Kar, Sayan
Rauch, Michael
Kumar, Amit
Leitus, Gregory
Ben-David, Yehoshoa
Milstein, David
ACS CATALYSIS, 2020, 10 (10): : 5511 - 5515
[40] One-Pot Synthesis of Bisindolylmethanes from Benzyl Alcohols and Indoles Using Catalytic Iodine and Molecular Oxygen under Visible Light Irradiation
Nobuta, Tomoya
Fujiya, Akitoshi
Tada, Norihiro
Miura, Tsuyoshi
Itoh, Akichika
SYNLETT, 2012, (20) : 2975 - 2979

← 1 2 3 4 5 →