Copper(I)-catalyzed efficient and stereoselective synthesis of (E)-vinyl selenides and tellurides by the reaction of potassium vinyltrifluoroborates with diphenyl dichalcogenides

被引:30
作者
Braga, Antonio L. [1 ]
Barcellos, Thiago [1 ]
Paixao, Marcio W. [1 ]
Deobald, Anna M. [1 ]
Godoi, Marcelo [1 ]
Stefani, Helio A. [1 ]
Cella, Rodrigo [1 ]
Sharma, Anuj [1 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
关键词
D O I
10.1021/om800052y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A mild, stereoselective, and effective strategy has been developed for the synthesis of (E)-vinyl selenides and (E)-vinyl tellurides by reaction of potassium vinyltrifluoroborates with the respective dichalcogenides using a copper salt as catalyst.
引用
收藏
页码:4009 / 4012
页数:4
相关论文
共 72 条
[1]   Tellurium in organic synthesis: synthesis of bioactive butenolides [J].
Bassora, Bruno K. ;
Da Costa, Carlos E. ;
Gariani, Rogerio A. ;
Comasseto, Joao V. ;
Dos Santos, Alcindo A. .
TETRAHEDRON LETTERS, 2007, 48 (08) :1485-1487
[2]   Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
TETRAHEDRON LETTERS, 1999, 40 (23) :4289-4292
[3]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[4]  
Batey RA, 2000, SYNTHESIS-STUTTGART, P990
[5]   Stereospecific synthesis of phosphono-(1Z,3E)-dienyl compounds from β-phenyltelluro-vinylphosphonates and -vinylphosphine oxides [J].
Braga, AL ;
Rhoden, CRB ;
Zeni, G ;
Silveira, CC ;
Andrade, LH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 682 (1-2) :35-40
[6]   Sonogashira cross-coupling reaction of organotellurium dichlorides with terminal alkynes [J].
Braga, AL ;
Lüdtke, DS ;
Vargas, F ;
Donato, RK ;
Silveira, CC ;
Stefani, MA ;
Zeni, G .
TETRAHEDRON LETTERS, 2003, 44 (09) :1779-1781
[7]   Synthesis of β-organotelluro vinylphosphine oxides by hydrotelluration of 1-alkynylphosphine oxides and their palladium-catalyzed cross-coupling with alkynes [J].
Braga, AL ;
Vargas, F ;
Zeni, G ;
Silveira, CC ;
de Andrade, LH .
TETRAHEDRON LETTERS, 2002, 43 (24) :4399-4402
[9]  
Campos M. M., 1962, TETRAHEDRON, V18, P527
[10]   Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts [J].
Cella, R ;
Cunha, RLOR ;
Reis, AES ;
Pimenta, DC ;
Klitzke, CF ;
Stefani, HA .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :244-250