Modular Approach to Silicon-Bridged Biaryls: Palladium-Catalyzed Intramolecular Coupling of 2-(Arylsilyl)aryl Triflates

被引:153
作者
Shimizu, Masaki [1 ]
Mochida, Kenji [1 ]
Hiyama, Tamejiro [1 ]
机构
[1] Kyoto Univ Katsura, Kyoto Univ, Dept Chem Mat, Grad Sch Engn,Nishikyo Ku, Kyoto 6158510, Japan
关键词
biaryls; C-H activation; luminescence; palladium; silicon;
D O I
10.1002/anie.200804146
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Bridge of Si: Intramolecular direct arylation of 2-(arylsilyl)aryl triflates is catalyzed smoothly by Pd(OAc) 2/PCy3 in the presence of Et2NH in dimethylacetamide (DMA), giving rise to the corresponding silicon-bridged biaryls in good to excellent yields. The new approach has led to the synthesis of a silicon-bridged 2-phenylindole (see scheme) that exhibits blue photoluminescence in the solid state with extremely high quantum yields. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9760 / 9764
页数:5
相关论文
共 91 条
[11]   Evolution of red organic light-emitting diodes: Materials and devices [J].
Chen, CT .
CHEMISTRY OF MATERIALS, 2004, 16 (23) :4389-4400
[12]   Silole-containing polymers: Chemistry and optoelectronic properties [J].
Chen, Junwu ;
Cao, Yong .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (17) :1714-1742
[13]   A general strategy for the facile synthesis of 2,7-dibromo-9-heterofluorenes [J].
Chen, RF ;
Fan, QL ;
Zheng, C ;
Huang, W .
ORGANIC LETTERS, 2006, 8 (02) :203-205
[14]  
CHERNYSHEV EA, 1985, ZH OBSHCH KHIM+, V55, P2314
[15]  
CHERNYSHEV EA, 1985, ZH OBSHCH KHIM+, V55, P2309
[16]   PREPARATION OF 5,5-DIMETHYLDIBENZOSILOLE [J].
COUTANT, RW ;
LEVY, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 10 (01) :175-&
[17]   Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls [J].
Dankwardt, JW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2428-2432
[18]   GROUP-14 METALLOLES .1. SYNTHESIS, ORGANIC-CHEMISTRY, AND PHYSICOCHEMICAL DATA [J].
DUBAC, J ;
LAPORTERIE, A ;
MANUEL, G .
CHEMICAL REVIEWS, 1990, 90 (01) :215-263
[19]   Organometallic generation and capture of ortho-arynes [J].
Dyke, Alan M. ;
Hester, Alison J. ;
Lloyd-Jones, Guy C. .
SYNTHESIS-STUTTGART, 2006, (24) :4093-4112
[20]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO