Cryptand-22 as an efficient ligand for the copper-catalyzed cross-coupling reaction of diorgano dichalcogenides with terminalalkynes leading to the synthesis of alkynyl chalcogenides

被引:24
作者
Mohammadi, Elmira [1 ]
Movassagh, Barahman [1 ]
机构
[1] KN Toosi Univ Technol, Dept Chem, Tehran, Iran
关键词
Cross-coupling; Catalysis; Dichalcogenides; Alkynyl chalcogenides; Terminal alkynes; STEREOSELECTIVE-SYNTHESIS; SELENIDES; TELLURIDES; SULFIDES; HALIDES; ORGANOSELENIUM; DISELENIDES; PRECURSORS; INHIBITORS; BROMIDES;
D O I
10.1016/j.tetlet.2014.01.088
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and efficient method for the cross-coupling reaction of diorgano dichalcogenides with terminal alkynes using copper iodide/cryptand-22 (CuI/C22) has been developed. This protocol gave allcynyl chalcogenides in moderate to excellent yields in the presence of K3PO4 as the base under aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1613 / 1615
页数:3
相关论文
共 49 条
[1]   Nucleophilic intramolecular cyclization reactions of alkynechalcogenolates [J].
Abramov, MA ;
Dehaen, W ;
D'hooge, B ;
Petrov, ML ;
Smeets, S ;
Toppet, S ;
Voets, M .
TETRAHEDRON, 2000, 56 (24) :3933-3940
[2]   An efficient and general procedure for the synthesis of alkynyl chalcogenides (selenides and tellurides) by alumina-supported Cu(II)-catalyzed reaction of alkynyl bromides and diphenyl dichalcogenides [J].
Ahammed, Sabir ;
Bhadra, Sukalyan ;
Kundu, Debasish ;
Sreedhar, Bojja ;
Ranu, Brindaban C. .
TETRAHEDRON, 2012, 68 (51) :10542-10549
[3]  
[Anonymous], 2009, ORG BIOMOL CHEM, DOI DOI 10.1039/b819137a
[4]   Additions of organocopper reagents and heteroatom nucleophiles to 1-phenylseleno-2-(p-toluenesulfonyl)ethyne.: Preparation of vinyl and allenic sulfones and formation of Michael, anti-Michael, and rearrangement products [J].
Back, TG ;
Bethell, RJ ;
Parvez, M ;
Wehrli, D .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7908-7919
[5]   Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes [J].
Bieber, LW ;
da Silva, MF ;
Menezes, PH .
TETRAHEDRON LETTERS, 2004, 45 (13) :2735-2737
[6]  
Bouillon JP, 2001, EUR J ORG CHEM, V2001, P3625, DOI 10.1002/1099-0690(200110)2001:19<3625::AID-EJOC3625>3.0.CO
[7]  
2-N
[8]   CONVENIENT PREPARATION OF ALKYNYL SELENIDES, SULFIDES AND TELLURIDES FROM TERMINAL ALKYNES AND PHENYLCHALCOGENYL HALIDES IN THE PRESENCE OF COPPER(I) IODIDE [J].
BRAGA, AL ;
SILVEIRA, CC ;
RECKZIEGEL, A ;
MENEZES, PH .
TETRAHEDRON LETTERS, 1993, 34 (50) :8041-8042
[9]   VICINAL DIFUNCTIONALIZATION OF ALKYNYL SELENIDES WITH LITHIUM BUTYLCYANOCUPRATE AND ELECTROPHILES [J].
BRAGA, AL ;
RECKZIEGEL, A ;
SILVEIRA, CC ;
COMASSETO, JV .
SYNTHETIC COMMUNICATIONS, 1994, 24 (08) :1165-1170
[10]  
BRAGA AL, 1984, SYNTHESIS-STUTTGART, P240