Easy Ruthenium-Catalysed Oxidation of Primary Amines to Nitriles under Oxidant-Free Conditions

被引：29

作者：

Achard, Thierry ^{[1
]}

Egly, Julien ^{[1
]}

Sigrist, Michel ^{[1
]}

Maisse-Francois, Aline ^{[1
]}

Bellemin-Laponnaz, Stephane ^{[1
]}

机构：

[1] Univ Strasbourg, Dept Mat Organ, IPCMS, CNRS UMR 7504, 23 Rue Loess,BP 43, F-67034 Strasbourg 2, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 58期

关键词：

acceptorless dehydrogenation; dehydrogenation; homogenous catalysis; nitrile; ruthenium; DEHYDROGENATION; COMPLEXES; CONVERSION;

D O I：

10.1002/chem.201902557

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A dehydrogenation of primary amine to give the corresponding nitrile under oxidant- and base-free conditions catalysed by simple [Ru(p-cym)Cl-2](2) with no extra ligand is reported. The system is highly selective for alkyl amines, whereas benzylamine derivatives gave the nitrile product together with the imine in a ratio ranging from 14:1 to 4:1 depending on the substrate. Preliminary mechanistic investigations have been performed to identify the key factors that govern the selectivity.

引用

页码：13271 / 13274

页数：4

共 50 条

[31] Catalytic Dehydrogenative Cyclization ofo-Teraryls under pH-Neutral and Oxidant-Free Conditions
Tsukamoto, Tatsuhiro
Dong, Guangbin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (35) : 15249 - 15253
[32] Electrochemical/I - Dual-Catalyzed Access to Sulfonated Pyrazoles under External Oxidant-Free Conditions
Ma, Jing
Yang, Jianjing
Yan, Kelu
Luo, Boju
Huang, Kexin
Wu, Ziling
Zhou, Yumeng
Zhu, Shuyun
Zhao, Xian-En
Wen, Jiangwei
SYNOPEN, 2023, 07 (02): : 272 - 276
[33] Electrochemical, Regioselective, and Stereoselective Synthesis of Allylic Thioethers and Selenoethers under Transition-Metal-Free and Oxidant-Free Conditions
Ucheniya, Kusum
Chouhan, Amreen
Yadav, Lalit
Jat, Pooja Kumari
Badsara, Satpal Singh
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 6096 - 6107
[34] Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
Singh, RahulKumar Rajmani
Liu, Rai-Shung
CHEMICAL COMMUNICATIONS, 2017, 53 (33) : 4593 - 4596
[35] A metal-free catalytic system for the oxidation of benzylic methylenes and primary amines under solvent-free conditions
Zhang, Jintang
Wang, Zhentao
Wang, Ye
Wan, Changfeng
Zheng, Xiaoqi
Wang, Zhiyong
GREEN CHEMISTRY, 2009, 11 (12) : 1973 - 1978
[36] Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles
Zhang, Ling-Juan
Xu, Mei-Chen
Liu, Jie
Zhang, Xian-Ming
RSC ADVANCES, 2016, 6 (77): : 73450 - 73453
[37] Oxidation of alcohols using iodosylbenzene as oxidant catalyzed by ruthenium complexes under mild reaction conditions
Yang, Zhi Wang
Kang, Qiao Xiang
Quan, Feng
Lei, Zi Qiang
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 261 (02) : 190 - 195
[38] Four-component synthesis of 3-aminomethylated imidazoheterocycles in EtOH under catalyst-free, oxidant-free and mild conditions
Gui, Qing-Wen
Wang, Bin-Bin
Zhu, Sha
Li, Fu-Long
Zhu, Meng-Xue
Yi, Min
Yu, Jia-Ling
Wu, Zhi-Lin
He, Wei-Min
GREEN CHEMISTRY, 2021, 23 (12) : 4430 - 4434
[39] Electrochemical radical annulation of 2-alkynyl biaryls with diselenides under catalyst-and chemical oxidant-free conditions
Jun Jiang
Ke-Li Wang
Xiao Li
Chao Wu
Hong-Tao Ji
Xiang Chen
Wei-Min He
ChineseChemicalLetters, 2023, 34 (12) : 172 - 175
[40] Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions
Yang, Cai-Yun
Zhang, De-Run
Hu, Lin-Ping
Li, Xia
Yang, Shi-Chen
Liu, Bo
Huang, Guo-Li
NEW JOURNAL OF CHEMISTRY, 2021, 45 (47) : 22243 - 22248

← 1 2 3 4 5 →