Hydrodehalogenation of Aryl Halides through Direct Electrolysis

被引：45

作者：

Ke, Jie ^{[1
]}

Wang, Hongling ^{[1
]}

Zhou, Liejin ^{[1
]}

Mou, Chengli ^{[2
]}

Zhang, Jingjie ^{[2
]}

Pan, Lutai ^{[2
]}

Chi, Yonggui Robin ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

[2] Guiyang Coll Tradit Chinese Med, Guiyang, Guizhou, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 28期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

electrochemistry; hydrodehalogenation; metal-free synthesis; organic halides; trialkylamines; ATOM TRANSFER OXIDATION; AROMATIC HALIDES; ALKYL; REDUCTIONS; GENERATION; CATALYSIS; ALKENYL; IODIDES;

D O I：

10.1002/chem.201901082

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalyst- and metal-free electrochemical hydrodehalogenation of aryl halides is disclosed. Our reaction by a flexible protocol is operated in an undivided cell equipped with an inexpensive graphite rod anode and cathode. Trialkylamines nBu(3)N/Et3N behave as effective reductants and hydrogen atom donors for this electrochemical reductive reaction. Various aryl and heteroaryl bromides worked effectively. The typically less reactive aryl chlorides and fluorides can also be smoothly converted. The utility of our method is demonstrated by detoxification of harmful pesticides and hydrodebromination of a dibrominated biphenyl (analogues of flame-retardants) in gram scale.

引用

页码：6911 / 6914

页数：4

共 57 条

[41] Polarity Reversal Catalysis in Radical Reductions of Halides by N-Heterocyclic Carbene Boranes [J].

Pan, Xiangcheng ;

Lacote, Emmanuel ;

Lalevee, Jacques ;

Curran, Dennis P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5669-5674

[42]

Povie G., 2016, ANGEW CHEM, V128, P11387

[43] Catechols as Sources of Hydrogen Atoms in Radical Deiodination and Related Reactions [J].

Povie, Guillaume ;

Ford, Leigh ;

Pozzi, Davide ;

Soulard, Valentin ;

Villa, Giorgio ;

Renaud, Philippe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11221-11225

[44]

SAHOO B, 2017, ANGEW CHEM, V129, P11394

[45] A Biomass-Derived Non-Noble Cobalt Catalyst for Selective Hydrodehalogenation of Alkyl and (Hetero)Aryl Halides [J].

Sahoo, Basudev ;

Surkus, Annette-Enrica ;

Pohl, Marga-Martina ;

Radnik, Joerg ;

Schneider, Matthias ;

Bachmann, Stephan ;

Scalone, Michelangelo ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (37) :11242-11247

[46] Free Radical Chemistry Enabled by Visible Light-Induced Electron Transfer [J].

Staveness, Daryl ;

Bosque, Irene ;

Stephenson, Corey R. J. .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2295-2306

[47] Cation flow method: A new approach to electrochemical conventional and combinatorial organic syntheses using electrochemical microflow systems [J].

Suga, S ;

Okajima, M ;

Fujiwara, K ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7941-7942

[48] Electrochemical Oxidative Cross-coupling with Hydrogen Evolution: A Green and Sustainable Way for Bond Formation [J].

Tang, Shan ;

Liu, Yichang ;

Lei, Aiwen .

CHEM, 2018, 4 (01) :27-45

[49] Chitosan-supported palladium catalyst. II. Chlorophenol dehalogenation [J].

Vincent, T ;

Spinelli, S ;

Guibal, E .

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2003, 42 (24) :5968-5976

[50] Electrochemical Arylation Reaction [J].

Waldvogel, Siegfried R. ;

Lips, Sebastian ;

Selt, Maximilian ;

Riehl, Barbara ;

Kampf, Christopher J. .

CHEMICAL REVIEWS, 2018, 118 (14) :6706-6765

← 1 2 3 4 5 6 →