Synthesis of Aryl Dithiocarbamates from Tetramethylthiuram Monosulfide (TMTM) and Aryl Boronic Acids: Copper-Catalyzed Construction of C(sp2)-S Bonds

被引：5

作者：

Xia, Xu-Ling ^{[1
]}

Zhu, Qi-Long ^{[1
]}

Chen, Jin-Quan ^{[1
]}

Shi, Zhen ^{[2
]}

Dong, Zhi-Bing ^{[1
,2
,3
,4
]}

机构：

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

[2] Hubei Minzu Univ, Hubei Key Lab Biol Resources Protect & Utilizat, Beijing 445000, Peoples R China

[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

[4] Minist Educ, Wuhan Inst Technol, Key Lab Green Chem Proc, Wuhan 430205, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 02期

关键词：

dithiocarbamates; tetramethylthiuram monosulfide; boronic acids; organosulfur; copper; CROSS-COUPLING REACTIONS; TETRAALKYLTHIURAM DISULFIDES; S-ARYLATION; EFFICIENT SYNTHESIS; ONE-POT; DERIVATIVES; SULFIDES; IODIDES; THIOLATION; THIOAMIDES;

D O I：

10.1055/a-1645-6040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient method for the synthesis of S-aryl dithiocarbamates is reported. By using tetramethylthiuram monosulfide (TMTM) and aryl boronic acids as starting materials, C(sp(2))-S bond-forming reactions proceed smoothly to give the desired aryl dithiocarbamates in good to excellent yields. The methodology features a simple procedure, broad functional group tolerance and excellent yields, whilst showing potential synthetic value for the preparation of a diverse range of biologically and pharmaceutically active compounds.

引用

页码：475 / 482

页数：8

共 50 条

[21] Facile synthesis of trifluoroethyl aryl ethers through copper-catalyzed coupling of CF3CH2OH with aryl- and heteroaryl boronic acids
Wang, Ruixin
Wang, Liang
Zhang, Kena
Li, Jingya
Zou, Dapeng
Wu, Yangjie
Wu, Yusheng
TETRAHEDRON LETTERS, 2015, 56 (33) : 4815 - 4818
[22] A Copper-Catalyzed Synthesis of Pyridoquinazolinones via C(sp2)-H Functionalization and Annulation of Benzoic Acids with 2-Aminopyridines
Kumar, Mahesh
Sharma, Anup Kumar
Ishu, Km
Singh, Krishna Nand
ORGANIC LETTERS, 2024, 26 (49) : 10517 - 10522
[23] Copper-Catalyzed Synthesis of N-aryl-D-Glucosamines from Arylboronic Acids
Tao, Chuanzhou
Liu, Feng
Xu, Bin
Cao, Zhiling
Wang, Huiyan
Liu, Weiwei
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2013, 32 (07) : 411 - 423
[24] Palladium-Catalyzed Intramolecular Amidation of C(sp2)-H Bonds: Synthesis of 4-Aryl-2-quinolinones
Inamoto, Kiyofumi
Saito, Tadataka
Hiroya, Kou
Doi, Takayuki
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11) : 3900 - 3903
[25] Copper-Catalyzed C(sp3)-C(sp2) Cross-Coupling: Synthesis of 4-Aryl-2-alkylamino-3-nitro-4H-chromenes
Rao, H. Surya Prakash
Rao, A. Veera Bhadra
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3646 - 3655
[26] Copper-catalyzed direct acyloxylation of C(sp~2)–H bonds with Benzoic acids
Sheng Zhao
Fa-Jie Chen
Bin Liu
Bing-Feng Shi
Science China(Chemistry), 2015, (08) : 1302 - 1309
[27] A Highly Efficient CuCl2-Catalyzed C-S Coupling of Aryl Iodides with Tetraalkylthiuram Disulfides: Synthesis of Aryl Dithiocarbamates
Cao, Qiang
Peng, Han-Ying
Cheng, Yu
Dong, Zhi-Bing
SYNTHESIS-STUTTGART, 2018, 50 (07): : 1527 - 1534
[28] Copper-Mediated Sulfonylation of Aryl C(sp2)-H Bonds with Sodium and Lithium Sulfinates
Liang, Shuai
Liu, Nai-Wei
Manolikakes, Georg
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) : 159 - 163
[29] Copper-catalyzed aerobic oxidation and cleavage/formation of C-S bond: a novel synthesis of aryl methyl sulfones from aryl halides and DMSO
Yuan, Gaoqing
Zheng, Junhua
Gao, Xiaofang
Li, Xianwei
Huang, Liangbin
Chen, Huoji
Jiang, Huanfeng
CHEMICAL COMMUNICATIONS, 2012, 48 (60) : 7513 - 7515
[30] Mechanistic and thermodynamic studies on directing group-assisted copper-catalyzed α-C(sp2)- H amination of aryl amines with alkylamines
Cui, Jinglei
Zheng, Wenrui
Jiao, Peilei
Jin, Hao
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2024, 1022

← 1 2 3 4 5 →