Nuclephilic ring opening of epoxides promoted by multi-site phase-transfer catalyst: An efficient and eco-friendly route to synthesis of β-hydroxythiocyanate

被引：12

作者：

Kiasat, Ali Reza ^{[1
]}

Mirzajani, Roya ^{[1
]}

Shalbaf, Haji ^{[1
]}

Tabatabaei, Tahereh ^{[1
]}

机构：

[1] Shahid Chamran Univ, Coll Sci, Dept Chem, Ahvaz 6135743169, Iran

来源：

CHINESE CHEMICAL LETTERS | 2009年 / 20卷 / 09期

关键词：

Multi-site phase-transfer catalyst; beta-Hydroxythiocyanate; Thiocyanohydrin; Epoxide; Ring opening; Regioselectivity; REGIOSELECTIVE CONVERSION; HYDROXY THIOCYANATES; MILD; ALKYLATION; OXIRANES; ANION; WATER; ACID;

D O I：

10.1016/j.cclet.2009.04.015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly effective and mild protocol for ring opening of epoxides with NH4SCN in the presence of catalytic amount of a multi-site phase-transfer catalyst, alpha,alpha',alpha ''-N-hexakis(triethylammoniummethylene chloride)-melaraine, is developed. A variety of beta-hydroxy thiocyanates as important intermediates in agricultural and pharmaceutical chemistry were obtained in high yields with excellent regioselectivity and in short reaction times. (C) 2009 Ali Reza Kiasat. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：1025 / 1029

页数：5

共 39 条

[1] Nuclephilic ring opening of epoxides promoted by multi-site phase-transfer catalyst:An efficient and eco-friendly route to synthesis of β-hydroxythiocyanate
Ali Reza Kiasat
Roya Mirzajani
Haji Shalbaf
Tahereh Tabatabaei
Chinese Chemical Letters, 2009, 20 (09) : 1025 - 1029
[2] Green Regioselective Azidolysis of Epoxides Catalyzed by Multi-site Phase-Transfer Catalyst
Kiasat, Ali Reza
Mirzajani, Roya
Shalbaf, Haji
Tabatabaei, Tahereh
Fallah-Mehrjardi, Mehdi
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2009, 56 (03) : 594 - 599
[3] PEG-SO3H as eco-friendly polymeric catalyst for regioselective ring opening of epoxides using thiocyanate anion in water:: An efficient route to synthesis of β-hydroxy thiocyanate
Kiasat, Ali Reza
Mehrjardi, Mehdi Fallah
CATALYSIS COMMUNICATIONS, 2008, 9 (06) : 1497 - 1500
[4] Highly efficient and eco-friendly protocol to functionalized imidazoles via ring-opening of α-nitro epoxides
Guo, Xiao
Shao, Jiaan
Liu, Huan
Chen, Binhui
Chen, Wenteng
Yu, Yongping
RSC ADVANCES, 2015, 5 (64): : 51559 - 51562
[5] Hydroxyapatite Nanorods Supported Boron Trifluoride: An Efficient, Reusable and Eco-friendly Heterogeneous Catalyst for Ring Opening of α-Epoxyketones
Saffar-Teluri, Ali
LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (09) : 683 - 687
[6] Mild Synthesis, Characterization, and Application of some Polythioester Polymers Catalyzed by Cetrimide Ionic Liquid as a Green and Eco-Friendly Phase-Transfer Catalyst
Ali, Azhar H.
Saleh, Mohanad Yakdhan
Owaid, Khalid Ahmed
IRANIAN JOURNAL OF CATALYSIS, 2023, 13 (01): : 73 - 83
[7] New quaternary phosphonium salt as multi-site phase-transfer catalyst for various alkylation reactions
Ponmuthu, Kottala Vijaya
Kumaraguru, Duraimurugan
Arockiam, Jesin Beneto
Velu, Sadhasivam
Sepperumal, Murugesan
Ayyanar, Siva
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (12) : 8345 - 8358
[8] New quaternary phosphonium salt as multi-site phase-transfer catalyst for various alkylation reactions
Kottala Vijaya Ponmuthu
Duraimurugan Kumaraguru
Jesin Beneto Arockiam
Sadhasivam Velu
Murugesan Sepperumal
Siva Ayyanar
Research on Chemical Intermediates, 2016, 42 : 8345 - 8358
[9] Synthesis of 4-(benzyloxy)biphenyl under a multi-site phase-transfer catalyst along with ultrasonication - A kinetic study
Sathiyaraj, M.
Ramya, R.
Tamizharasu, G.
Rajendran, V.
Venkatesh, P.
INDIAN JOURNAL OF CHEMICAL TECHNOLOGY, 2022, 29 (06) : 721 - 728
[10] β-Cyclodextrin based polyurethane as eco-friendly polymeric phase transfer catalyst in nucleophilic substitution reactions of benzyl halides in water: An efficient route to synthesis of benzyl thiocyanates and acetates
Kiasat, Ali Reza
Nazari, Simin
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (05) : 1056 - 1058

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