Thiocyanate radical mediated dehydration of aldoximes with visible light and air

被引：32

作者：

Ban, Yong-Liang ^{[1
]}

Dai, Jian-Ling ^{[1
]}

Jin, Xiao-Ling ^{[1
]}

Zhang, Qing-Bao ^{[1
]}

Liu, Qiang ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 65期

关键词：

PHOTOCATALYTIC ANION OXIDATION; PRIMARY AMIDES; ARYL IODIDES; NITRILES; EFFICIENT; CONVERSION; MILD; CYANATION; CATALYST; DIFUNCTIONALIZATION;

D O I：

10.1039/c9cc05354a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

引用

页码：9701 / 9704

页数：4

共 50 条

[1]

Adak S, 1997, J BIOL CHEM, V272, P11049

[2] Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates [J].

Anderson, BA ;

Bell, EC ;

Ginah, FO ;

Harn, NK ;

Pagh, LM ;

Wepsiec, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8224-8228

[3] Recent Advances in Transition Metal-Catalyzed Hydrogenation of Nitriles [J].

Bagal, Dattatraya B. ;

Bhanage, Bhalchandra M. .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :883-900

[4] Indium-mediated facile dehydration and Beckmann rearrangement of grimes [J].

Barman, DC ;

Thakur, AJ ;

Prajapati, D ;

Sandhu, JS .

CHEMISTRY LETTERS, 2000, (10) :1196-1197

[5] Metal-Involving Synthesis and Reactions of Oximes [J].

Bolotin, Dmitrii S. ;

Bokach, Nadezhda A. ;

Demakova, Marina Ya. ;

Kukushkin, Vadim Yu. .

CHEMICAL REVIEWS, 2017, 117 (21) :13039-13122

[6] Recent advances in the chemistry of organic thiocyanates [J].

Castanheiro, Thomas ;

Suffert, Jean ;

Donnard, Morgan ;

Gulea, Mihaela .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :494-505

[7] Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides [J].

Cristau, HJ ;

Ouali, A ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2483-2492

[8] Organotellurium catalysis-enabled utilization of molecular oxygen as oxidant for oxidative deoximation reactions under solvent-free conditions [J].

Deng, Xin ;

Cao, Hongen ;

Chen, Chao ;

Zhou, Hongwei ;

Yu, Lei .

SCIENCE BULLETIN, 2019, 64 (17) :1280-1284

[9] Some recent applications of α-amino nitrile chemistry [J].

Enders, D ;

Shilvock, JP .

CHEMICAL SOCIETY REVIEWS, 2000, 29 (05) :359-373

[10] A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles [J].

Fan, Weigang ;

Yang, Qi ;

Xu, Fengshan ;

Li, Pixu .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) :10588-10592

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