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

被引：38

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

[1] SELECTIVE HYDROGENATION OF UNSATURATED CARBON-CARBON BONDS WITH RHODIUM COMPLEXES
CANDLIN, JP
OLDHAM, AR
[J]. DISCUSSIONS OF THE FARADAY SOCIETY, 1968, (46): : 60 - &
[2] Transition Metal-Free CO2 Fixation into New Carbon-Carbon Bonds
Cherubini-Celli, Alessio
Mateos, Javier
Bonchio, Marcella
Dell'Amico, Luca
Companyo, Xavier
[J]. CHEMSUSCHEM, 2018, 11 (18) : 3056 - 3070
[3] Metal-Free Decarboxylation of α,β-Unsaturated Carboxylic Acids for Carbon-Carbon and Carbon-Heteroatom Coupling Reactions
Xu, Xianjun
Van der Eycken, Erik V.
Feng, Huangdi
[J]. CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1780 - 1792
[4] Formation of Carbon-Carbon Bonds Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions
Li, Xiaoxian
Liu, Tongxing
Zhang, Beibei
Zhang, Dongke
Shi, Haofeng
Yu, Zhenyang
Tao, Shanqing
Du, Yunfei
[J]. CURRENT ORGANIC CHEMISTRY, 2020, 24 (01) : 74 - 103
[5] REDUCTION OF UNSATURATED CARBON-CARBON BONDS WITH SODIUM BOROTRITIDE/NICKEL CHLORIDE
Tang, Yui S.
Ho, Jonathan Z.
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (5-6): : 437 - 440
[6] Metal-Organic Frameworks (MOFs) as Heterogeneous Catalysts for the Chemoselective Reduction of Carbon-Carbon Multiple Bonds with Hydrazine
Dhakshinamoorthy, Amarajothi
Alvaro, Mercedes
Garcia, Hermenegildo
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) : 2271 - 2276
[7] Metal-Free Chemoselective Hydrogenation of Nitroarenes by N-Doped Carbon Nanotubes via In Situ Polymerization of Pyrrole
Li, Guozhu
Zheng, Shuyi
Wang, Li
Zhang, Xiangwen
[J]. ACS OMEGA, 2020, 5 (13): : 7519 - 7528
[8] Selective Hydrogenation of Unsaturated Carbon-Carbon Bonds in Aromatic-Containing Platform Molecules
Schwartz, Thomas J.
Lyman, Spencer D.
Motagamwala, Ali Hussain
Mellmer, Max A.
Dumesic, James A.
[J]. ACS CATALYSIS, 2016, 6 (03): : 2047 - 2054
[9] Allylsilylation of carbon-carbon and carbon-oxygen unsaturated bonds via a radical process
Miura, K
Saito, H
Nakagawa, T
Hondo, T
Tateiwa, J
Sonoda, M
Hosomi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17): : 5740 - 5741
[10] Studies on transition metal-catalyzed carbostannylations of carbon-carbon unsaturated bonds
Shirakawa, E
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2004, 62 (06) : 616 - 628

← 1 2 3 4 5 →