Metal-free chemoselective hydrogenation of unsaturated carbon-carbon bonds via cathodic reduction

被引：41

作者：

Qin, Yongwei ^{[1
]}

Lu, Jingjun ^{[1
]}

Zou, Zirong ^{[1
]}

Hong, Huanliang ^{[1
]}

Li, Yamei ^{[1
]}

Li, Yibiao ^{[1
]}

Chen, Lu ^{[1
]}

Hu, Jinhui ^{[1
]}

Huang, Yubing ^{[1
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529090, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 14期

关键词：

CATALYZED CONJUGATE REDUCTION; N-HETEROCYCLIC CARBENE; ELECTROREDUCTIVE CYCLIZATION; KETONES; IRON; COMPLEXES; HYDRIDES; ALKYNES; AMINES; ALKENE;

D O I：

10.1039/d0qo00547a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward protocol for efficient and highly selective hydrogenation of unsaturated carbon-carbon bondsviaelectrochemical reduction has been reported. A series of chain alkanes and carbonyl compounds are produced under metal-free and external-reductant-free electrolytic conditions. Scale-up experiments have exhibited the potential applications of this protocol in practical synthesis. Deuterium-labelling experiments demonstrate that both DMSO and H2O in the reaction system can provide hydrogen atoms for the reaction.

引用

页码：1817 / 1822

页数：6

共 50 条

[21] Free rotation about carbon-carbon bonds
Kassel, LS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 2745 - 2746
[22] Metal-free and selective cleavage of unstrained carbon-carbon single bonds: Synthesis of β-ketosulfones from β-chlorohydrins and sodium sulfinates
Li, Yanni
Liang, Deqiang
Chang, Yu
Li, Xiangguang
Fu, Shaoguang
Yuan, Yunli
Wang, Baoling
SYNTHETIC COMMUNICATIONS, 2017, 47 (22) : 2044 - 2052
[23] A metal-free transfer hydrogenation:: Organocatalytic conjugate reduction of α,β-unsaturated aldehydes
Yang, JW
Fonseca, MTH
List, B
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (48) : 6660 - 6662
[24] Al-containing mesoporous carbon as effective catalysts for the chemoselective reduction of carbon-carbon double bonds in nitrostilbene derivatives
Wang, Liuchang
Zheng, Yanjun
Zhang, Xiquan
Gu, Hongmei
Li, Jiang
Wang, Wei
Li, Baolin
APPLIED CATALYSIS A-GENERAL, 2013, 456 : 23 - 29
[25] Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds
Yang, Heng
Zhou, Zhijie
Tang, Conghui
Chen, Feng
CHINESE CHEMICAL LETTERS, 2024, 35 (06)
[26] INTERMOLECULAR AND INTRAMOLECULAR REACTIONS OF ARYLAZOMETHYLENETRIPHENYLPHOSPHORANES WITH UNSATURATED CARBON-CARBON BONDS
ALEMAGNA, A
DELBUTTERO, P
LICANDRO, E
MAIORANA, S
GAZZETTA CHIMICA ITALIANA, 1981, 111 (7-8): : 285 - 288
[27] Metal-Free Catalyst for the Chemoselective Methylation of Amines Using Carbon Dioxide as a Carbon Source
Das, Shoubhik
Bobbink, Felix D.
Laurenczy, Gabor
Dyson, Paul J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (47) : 12876 - 12879
[28] Progresses in the fluorination addition reactions of unsaturated carbon-carbon bonds
Chen, XB
An, ZW
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2002, 22 (10) : 694 - 701
[29] Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds
Heng Yang
Zhijie Zhou
Conghui Tang
Feng Chen
Chinese Chemical Letters, 2024, 35 (06) : 97 - 111
[30] Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds
Heng Yang
Zhijie Zhou
Conghui Tang
Feng Chen
Chinese Chemical Letters, 2024, (06) : 97 - 111

← 1 2 3 4 5 →