Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols

被引：38

作者：

Sreedhar, B. ^{[1
]}

Reddy, P. Surendra ^{[1
]}

Reddy, M. Amarnath ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHESIS-STUTTGART | 2009年 / 10期

关键词：

heteroaryl halides; thiophenol; SNAr reaction; water; 2-thiopyridines; EFFICIENT SYNTHESIS; ARYL; EPOXIDES;

D O I：

10.1055/s-0029-1216644

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products.

引用

页码：1732 / 1738

页数：7

共 50 条

[1] Ligand and base-free Heck reaction with heteroaryl halides
Kantam, M. Lakshmi
Reddy, P. Vishnuvardhan
Srinivas, P.
Bhargava, Suresh
[J]. TETRAHEDRON LETTERS, 2011, 52 (34) : 4490 - 4493
[2] Water promoted catalyst-free anti-Markovnikov addition of thiols to styrenes
Movassagh, Barahman
Navidi, Mozhgan
[J]. ARKIVOC, 2008, : 47 - 53
[3] Rapid microwave-promoted catalyst- and base-free Suzuki-type coupling reaction in water
Yan, Jie
Zhu, Min
Zhou, Zhongshi
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) : 2060 - 2062
[4] Base-Free and Catalyst-Free Synthesis of Functionalized Dihydrobenzoxazoles via Vinylogous Carbonate to Carbamate Rearrangement
Das, Tamal Kanti
Mondal, Santigopal
Gonnade, Rajesh G.
Bije, Akkattu T.
[J]. ORGANIC LETTERS, 2017, 19 (20) : 5597 - 5600
[5] Catalyst-Free Aldol Reaction in a Water Medium
Yao, Weirong
Cui, Yanli
Wang, Peipei
Mao, Yangyi
[J]. LETTERS IN ORGANIC CHEMISTRY, 2016, 13 (04) : 293 - 296
[6] Catalyst-free, visible-light-promoted S-H insertion reaction between thiols and α-diazoesters
Yang, Jingya
Wang, Ganggang
Chen, Shuwen
Ma, Ben
Zhou, Hongyan
Song, Menghui
Liu, Cai
Huo, Congde
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (46) : 9494 - 9498
[7] Base-Free Cu(II)-Catalyzed Coupling Reaction of Arylboronic Acids and Thiols
Yang, Minghua
Pei, Ji
Yan, Guobing
Weng, Qiuyue
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (02) : 343 - 347
[8] Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water
Khatik, Gopal L.
Kumar, Raj
Chakraborti, Asit K.
[J]. ORGANIC LETTERS, 2006, 8 (11) : 2432 - 2436
[9] A density functional theory study on mechanism and substituent effects of a base-free and catalyst-free synthesis of functionalized dihydrobenzoxazoles
Zhang, Huimin
Bai, Huining
Guo, Yuen
Wei, Donghui
Chen, Hui
Zhu, Yanyan
Zhang, Wenjing
[J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2019, 119 (06)
[10] Gold catalyst recycling study in base-free glucose oxidation reaction
Megias-Sayago, C.
Bobadilla, L. F.
Ivanova, S.
Penkova, A.
Centeno, M. A.
Odriozola, J. A.
[J]. CATALYSIS TODAY, 2018, 301 : 72 - 77

← 1 2 3 4 5 →