Nickel-Catalyzed Direct Cross-Coupling of Aryl Thioether with Aryl Bromide

被引：41

作者：

Ma, Na-Na ^{[1
]}

Hu, Xuan-Bo ^{[1
]}

Wu, Yuan-Shuai ^{[1
]}

Zheng, Ya-Wen ^{[1
]}

Ma, Mengtao ^{[2
]}

Chu, Xue-Qiang ^{[1
]}

Xu, Hao ^{[1
]}

Luo, Haiqing ^{[3
]}

Shen, Zhi-Liang ^{[1
]}

机构：

[1] Nanjing Tech Univ, Tech Inst Fluorochemistry TIF, Inst Adv Synth, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

[2] Nanjing Forestry Univ, Coll Sci, Nanjing 210037, Peoples R China

[3] Gannan Normal Univ, Dept Chem & Chem Engn, Ganzhou 341000, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 10期

基金：

中国国家自然科学基金;

关键词：

CARBON-SULFUR; REACTIVITY; ACTIVATION; INSERTION; REAGENTS; SULFIDES; HALIDES;

D O I：

10.1021/acs.orglett.3c00518

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward cross-coupling of aryl thioether with aryl bromide with the aid of nickel salt, magnesium, and lithium chloride in tetrahydrofuran at ambient temperature was accomplished. The one-pot reactions proceeded efficiently via C-S bond cleavage to produce the desired biaryls in modest to good yields, avoiding the use of pregenerated or commercial organometallic reagents.

引用

页码：1771 / 1775

页数：5

共 43 条

[1] Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].

Alphonse, FA ;

Suzenet, F ;

Keromnes, A ;

Lebret, B ;

Guillaumet, G .

ORGANIC LETTERS, 2003, 5 (06) :803-805

[2] Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides [J].

Arendt, Kevin M. ;

Doyle, Abigail G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) :9876-9880

[3] Cobalt-catalyzed C-SMe bond activation of heteroaromatic thioethers [J].

Begouin, Jeanne-Marie ;

Rivard, Michael ;

Gosmini, Corinne .

CHEMICAL COMMUNICATIONS, 2010, 46 (32) :5972-5974

[4]

Blümke T, 2010, NAT CHEM, V2, P313, DOI [10.1038/nchem.590, 10.1038/NCHEM.590]

[5] Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides [J].

Chen, Bing-Zhi ;

Zhi, Man-Ling ;

Wang, Chuang-Xin ;

Chu, Xue-Qiang ;

Shen, Zhi-Liang ;

Loh, Teck-Peng .

ORGANIC LETTERS, 2018, 20 (07) :1902-1905

[6] Nickel-catalyzed direct cross-coupling of heterocyclic phosphonium salts with aryl bromides [J].

Cui, Yan-Ying ;

Li, Wen-Xin ;

Ma, Na-Na ;

Shen, Chuanji ;

Zhou, Xiaocong ;

Chu, Xue-Qiang ;

Rao, Weidong ;

Shen, Zhi-Liang .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) :6931-6936

[7] Chemo-Controlled Cross-Coupling of Di(hetero)aryl Disulfides with Grignard Reagents: C-C vs. C-S Bond Formation [J].

Du, Bao-Xin ;

Quan, Zheng-Jun ;

Da, Yu-Xia ;

Zhang, Zhang ;

Wang, Xi-Cun .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) :1270-1276

[8] Heteroaromatic thioether-organostannane cross-coupling [J].

Egi, M ;

Liebeskind, LS .

ORGANIC LETTERS, 2003, 5 (06) :801-802

[9] Cross-Electrophile Coupling: Principles of Reactivity and Selectivity [J].

Everson, Daniel A. ;

Weix, Daniel J. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :4793-4798

[10] Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations [J].

Gu, Jun ;

Wang, Xuan ;

Xue, Weichao ;

Gong, Hegui .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1411-1421

← 1 2 3 4 5 →