Copper-Catalyzed Silacarboxylation of Internal Alkynes by Employing Carbon Dioxide and Silylboranes

被引:141
作者
Fujihara, Tetsuaki [1 ]
Tani, Yosuke [1 ]
Semba, Kazuhiko [1 ]
Terao, Jun [1 ]
Tsuji, Yasushi [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Kyoto 6158510, Japan
关键词
alkynes; carboxylation; copper; homogeneous catalysis; silylborane; C-H BONDS; DIRECT CARBOXYLATION; TERMINAL ALKYNES; PALLADIUM; HYDROCARBOXYLATION; SILABORATION; COMPLEXES; CLEAVAGE; TRANSFORMATION; BENZOSILOLES;
D O I
10.1002/anie.201207148
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Silalactones: The copper-catalyzed reaction of internal alkynes with (dimethylphenylsilyl)pinacolborane (Me 2PhSi-B(pin)) as the silicon source and CO 2 at atmospheric pressure afforded silalactones selectively in good to high yields. The silalactones can be used as substrates for the Hiyama cross-coupling reaction as demonstrated for one substrate. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11487 / 11490
页数:4
相关论文
共 51 条
[1]  
[Anonymous], 2010, ANGEW CHEM-GER EDIT
[2]  
[Anonymous], 2010, ANGEW CHEM
[3]  
[Anonymous], 2011, ANGEW CHEM-GER EDIT
[4]  
[Anonymous], 2011, ANGEW CHEM-GER EDIT
[5]  
Aresta M., 2010, CARBON DIOXIDE CHEM
[6]   Iridium-Catalyzed Preparation of Silylboranes by Silane Borylation and Their Use in the Catalytic Borylation of Arenes [J].
Boebel, Timothy A. ;
Hartwig, John F. .
ORGANOMETALLICS, 2008, 27 (22) :6013-6019
[7]   Carboxylation of N-H/C-H Bonds Using N-Heterocyclic Carbene Copper(I) Complexes [J].
Boogaerts, Ine I. F. ;
Fortman, George C. ;
Furst, Marc R. L. ;
Cazin, Catherine S. J. ;
Nolan, Steven P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) :8674-8677
[8]   Carboxylation of C-H Bonds Using N-Heterocyclic Carbene Gold(I) Complexes [J].
Boogaerts, Ine I. F. ;
Nolan, Steven P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :8858-+
[9]   Structural and spectroscopic studies on three-coordinate complexes of copper(I) halides with tricyclohexylphosphine [J].
Bowmaker, GA ;
Boyd, SE ;
Hanna, JV ;
Hart, RD ;
Healy, PC ;
Skelton, BW ;
White, AH .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (13) :2722-2730
[10]  
Cokoja M., 2011, ANGEW CHEM, V123, P8662, DOI DOI 10.1002/ANGE.201102010