Synthesis of Phenyl Dithiocarbamates Starting from Sodium Dialkyldithiocarbamates and Aryl Boronic Acids: a Copper Catalyzed S-Arylation

被引：36

作者：

Gao, Ming-Yuan ^{[1
]}

Xu, Wan ^{[1
]}

Zhang, Shi-Bo ^{[1
]}

Li, Yue-Sheng ^{[3
]}

Dong, Zhi-Bing ^{[1
,2
]}

机构：

[1] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Hubei, Peoples R China

[2] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany

[3] Hubei Univ Sci & Technol, Nonpower Nucl Technol Collaborat Innovat Ctr, Xianning 437100, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 47期

基金：

中国国家自然科学基金;

关键词：

Dialkyldithiocarbamates; Boronic acid; Arylation; C-S coupling; Copper; ANTIFUNGAL ACTIVITY; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; DERIVATIVES; ZINC; 2-AMINOBENZOTHIAZOLES; ISOTHIOCYANATES; CHEMISTRY; IODIDES; IODINE;

D O I：

10.1002/ejoc.201801271

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and efficient protocol for the S-arylation of sodium dialkyldithiocarbamates was developed. With the catalysis of copper(I) bromide, sodium dialkyldithiocarbamates coupled with aryl boronic acids giving the C-S coupling products smoothly in good to excellent yields. This protocol features easily available starting materials, easy performance, short reaction time, broad substrate scope and good yields, showing its potential synthetic value for the convenient preparation of some potentially biologically active compounds.

引用

页码：6693 / 6698

页数：6

共 44 条

[1] Copper-Catalyzed S-Arylation Starting from Arylboronic Acids and Tetraalkylthiuram Disulfide
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Gao, Fan
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (06) : 821 - 828
[2] Synthesis of Aryl Dithiocarbamates from Tetramethylthiuram Monosulfide (TMTM) and Aryl Boronic Acids: Copper-Catalyzed Construction of C(sp2)-S Bonds
Xia, Xu-Ling
Zhu, Qi-Long
Chen, Jin-Quan
Shi, Zhen
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SYNTHESIS-STUTTGART, 2022, 54 (02): : 475 - 482
[3] Copper-Catalyzed Synthesis of S-Aryl Dithiocarbamates from Tetraalkylthiuram Disulfides and Aryl Iodides in Water
Wu, Xiang-mei
Yan, Guo-bing
SYNLETT, 2019, 30 (05) : 610 - 614
[4] Copper catalyzed arylation with boronic acids for the synthesis of N1-aryl purine nucleosides
Strouse, JJ
Jeselnik, M
Tapaha, F
Jonsson, CB
Parker, WB
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TETRAHEDRON LETTERS, 2005, 46 (34) : 5699 - 5702
[5] Efficient Copper-Catalyzed S-Arylation of Thiols with Aryl Bromides and Chlorides
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Li, Xiaoying
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[6] EFFICIENT COPPER-CATALYZED DOUBLE S-ARYLATION OF ARYL HALIDES WITH SODIUM SULFIDE IN PEG-400
Chen, Junmin
Zhang, Yimin
Liu, Li
Yuan, Tangjun
Yi, Fei
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (11) : 1284 - 1290
[7] Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides
Liang, Qingjin
Wells, Lucille A.
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (11) : 6310 - 6318
[8] Copper-Catalyzed C(sp2)-S Coupling Reactions for the Synthesis of Aryl Dithiocarbamates with Thiuram Disulfide Reagents
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ORGANIC LETTERS, 2017, 19 (21) : 5916 - 5919
[9] Efficient Copper(I)-Catalyzed S-Arylation of KSCN with Aryl Halides in PEG-400
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CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (03) : 651 - 655
[10] Copper-Catalyzed C-S Formation for the Synthesis of Benzyl Phenyl Sulfides from Dithiocarbamates
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Yang, Cheng-Li
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SYNTHESIS-STUTTGART, 2022, 54 (18): : 4104 - 4110

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