Selectively synthesis of cyclic di- and trithiocarbonates by N-heterocyclic carbene/LiCl(Br) catalyzed addition of carbon disulfide to epoxides

被引：19

作者：

Mei, Congmin ^{[1
,2
]}

Li, Xu ^{[1
,2
]}

Liu, Lihuai ^{[1
,2
]}

Cao, Changsheng ^{[1
,2
]}

Pang, Guangsheng ^{[3
]}

Shi, Yanhui ^{[1
,2
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China

[2] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China

[3] Jilin Univ, Coll Chem, State Key Lab Inorgan Synth & Preparat Chem, Changchun 130012, Jilin, Peoples R China

来源：

TETRAHEDRON | 2017年 / 73卷 / 38期

基金：

中国国家自然科学基金;

关键词：

Carbon disulfide; Trithiocarbonate; Dithiocarbonate; Epoxide; 5-MEMBERED DITHIOCARBONATE; CATIONIC ISOMERIZATION; CO2; COPOLYMERIZATION; POLYMERIZATION; DIOXIDE;

D O I：

10.1016/j.tet.2017.08.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbon disulfide is an abundant, inexpensive and readily available material. One of the main challenges in the reaction of epoxides with CS2 is to control the chemoselectivity as a variety of compounds would be formed in the reaction. A simple and convenient method toward selectively synthesis of oxathiolane and trithiocarbonate from epoxides with CS2 catalyzed by NHC/LiCI(Br) under the neat conditions has been developed. This catalytic system exhibits excellent activity and selectivity in cycloaddition reactions of carbon disulfide to terminal epoxides. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：5706 / 5714

页数：9

共 50 条

[1] Synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide catalyzed by N-heterocyclic carbene
Jinsong Cao
Meng Yu
Hanzhu Li
Liang Wang
Xu Zhu
Guangying Wang
Yanhui Shi
Changsheng Cao
Research on Chemical Intermediates, 2015, 41 : 5323 - 5330
[2] Synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide catalyzed by N-heterocyclic carbene
Cao, Jinsong
Yu, Meng
Li, Hanzhu
Wang, Liang
Zhu, Xu
Wang, Guangying
Shi, Yanhui
Cao, Changsheng
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (08) : 5323 - 5330
[3] Atom economical synthesis of di- and trithiocarbonates by the lithium tert-butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes
Diebler, J.
Spannenberg, A.
Werner, T.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (31) : 7480 - 7489
[4] Aluminium(salen) and Tetrabutylammonium Bromide Catalysed Synthesis of Cyclic Di- and Trithiocarbonates from Epoxides and Carbon Disulfide
North, Michael
Villuendas, Pedro
SYNLETT, 2010, (04) : 623 - 627
[5] Titanium(salen)-Catalysed Synthesis of Di- and Trithiocarbonates from Epoxides and Carbon Disulfide
Beattie, Christopher
North, Michael
CHEMCATCHEM, 2014, 6 (05) : 1252 - 1259
[6] N-heterocyclic carbene-pyridine ligand coordinated Mo(II) complexes catalyzed synthesis of cyclic carbonates from carbon dioxide and epoxides
Li, Jianwen
Tao, Sheng
Chen, Fei
Li, Min
Liu, Ning
JOURNAL OF CO2 UTILIZATION, 2023, 69
[7] N-Heterocyclic Carbene Catalyzed Synthesis of Trisubstituted Epoxides via Tandem Amidation/Epoxidation Sequence
Devi, E. Sankari
Pavithra, Thangavel
Tamilselvi, A.
Nagarajan, Subbiah
Sridharan, Vellaisamy
Maheswari, C. Uma
ORGANIC LETTERS, 2020, 22 (09) : 3576 - 3580
[8] N-Heterocyclic carbene catalyzed synthesis of oxime esters
Enders, Dieter
Grossmann, Andre
Van Craen, David
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (01) : 138 - 141
[9] N-heterocyclic carbene-catalyzed synthesis of polyurethanes
Coutelier, Olivier
El Ezzi, Mohammad
Destarac, Mathias
Bonnette, Fabien
Kato, Tsuyoshi
Baceiredo, Antoine
Sivasankarapillai, Gopakumar
Gnanou, Yves
Taton, Daniel
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[10] N-Heterocyclic carbene-catalyzed conversion of α-amino alcohols to their corresponding epoxides
Goralski, Sean
Saliba, Bianca
Overly, Kenneth
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253

← 1 2 3 4 5 →