Silylium ion-promoted dehydrogenative cyclization: synthesis of silicon-containing compounds derived from alkynes

被引:27
作者
Arii, Hidekazu [1 ]
Kurihara, Takashi [1 ]
Mochida, Kunio [1 ]
Kawashima, Takayuki [2 ]
机构
[1] Gakushuin Univ, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
[2] Gunma Univ, Grad Sch Sci & Technol, Gunma 3768515, Japan
关键词
LEWIS-ACID CATALYST; B(C6F5)(3)-CATALYZED HYDROSILYLATION; REDUCTION; CATIONS; HYDRODEFLUORINATION; CO2;
D O I
10.1039/c4cc01648c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of dialkylbenzylsilane (1) with trityl tetrakis(pentafluorophenyl) borate (TPFPB) in the presence of terminal or internal alkynes (3) and 2,6-di-tert-butyl-4-methylpyridine gave the corresponding 1,2-dihydro-2-silanaphthalene derivatives (4) in 34-82% yields.
引用
收藏
页码:6649 / 6652
页数:4
相关论文
共 35 条
[21]   A Unique Transition Metal-Stabilized Silicon Cation [J].
Muether, Kristine ;
Froehlich, Roland ;
Mueck-Lichtenfeld, Christian ;
Grimme, Stefan ;
Oestreich, Martin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) :12442-12444
[22]   Self-regeneration of a silylium ion catalyst in carbonyl reduction [J].
Muether, Kristine ;
Oestreich, Martin .
CHEMICAL COMMUNICATIONS, 2011, 47 (01) :334-336
[23]   The X-ray structure of a vinyl cation [J].
Müller, T ;
Juhasz, M ;
Reed, CA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1543-1546
[24]  
Müller T, 2000, ANGEW CHEM INT EDIT, V39, P3074
[25]   σ-delocalization versus π-resonance in α-aryl-substituted vinyl cations [J].
Müller, T ;
Margraf, D ;
Syha, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10852-10860
[26]   Triethylsilyl Perfluoro-Tetraphenylborate, [Et3Si+][F20-BPh4-], a Widely Used Nonexistent Compound [J].
Nava, Matthew ;
Reed, Christopher A. .
ORGANOMETALLICS, 2011, 30 (17) :4798-4800
[27]   Hydrogen- and fluorine-bridged disilyl cations and their use in catalytic C-F activation [J].
Panisch, Robin ;
Bolte, Michael ;
Mueller, Thomas .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9676-9682
[28]   Onium ions. Part 57. Preparation and NMR study of silylated carboxonium ions [J].
Prakash, GKS ;
Bae, CS ;
Rasul, G ;
Olah, GA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1297-1301
[29]   The silylium ion problem, R3Si+.: Bridging organic and inorganic chemistry [J].
Reed, CA .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (06) :325-332
[30]   Conclusive evidence for an SN2-Si mechanism in the B(C6F5)3-catalyzed hydrosilylation of carbonyl compounds:: Implications for the related hydrogenation [J].
Rendler, Sebastian ;
Oestreich, Martin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) :5997-6000