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

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 50期

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

页码：6649 / 6652

页数：4

共 35 条

[1] Hydrodefluorination of perfluoroalkyl groups using silylium-carborane catalysts
Douvris, Christos
Ozerov, Oleg V.
[J]. SCIENCE, 2008, 321 (5893) : 1188 - 1190
[2] Synthesis of 2,6-diarylphenyldimethylsilyl cations:: Polar-π distribution of cation character
Duttwyler, Simon
Do, Quyen-Quyen
Linden, Anthony
Baldridge, Kim K.
Siegel, Jay S.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) : 1719 - 1722
[3] Application of the sila-Friedel-Crafts reaction to the synthesis of π-extended silole derivatives and their properties
Furukawa, Shunsuke
Kobayashi, Junji
Kawashima, Takayuki
[J]. DALTON TRANSACTIONS, 2010, 39 (39) : 9329 - 9336
[4] Development of a Sila-Friedel-Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives
Furukawa, Shunsuke
Kobayashi, Junji
Kawashima, Takayuki
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) : 14192 - +
[5] Strong counteranion effects on the catalytic activity of cationic silicon Lewis acids in Mukaiyama aldol and Diels-Alder reactions
Hara, K
Akiyama, R
Sawamura, M
[J]. ORGANIC LETTERS, 2005, 7 (25) : 5621 - 5623
[6] Trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide as a super Lewis acid catalyst for the condensation of trimethylhydroquinone with isophytol
Hasegawa, A
Ishihara, K
Yamamoto, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) : 5731 - 5733
[7] Catalytic Trimerization of Bis-silylated Diazomethane
Ibad, Muhammad Farooq
Langer, Peter
Reiss, Fabian
Schulz, Axel
Villinger, Alexander
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17757 - 17768
[8] Silylium-Arene Adducts: An Experimental and Theoretical Study
Ibad, Muhammad Farooq
Langer, Peter
Schulz, Axel
Villinger, Alexander
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) : 21016 - 21027
[9] gem-Disubstituent effect:: Theoretical basis and synthetic applications
Jung, ME
Piizzi, G
[J]. CHEMICAL REVIEWS, 2005, 105 (05) : 1735 - 1766
[10] Deoxygenative Reduction of Carbon Dioxide to Methane, Toluene, and Diphenylmethane with [Et2Al]+ as Catalyst
Khandelwal, Manish
Wehmschulte, Rudolf J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (29) : 7323 - 7326

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