Synthesis of aryltriethoxysilanes via rhodium(I)-catalyzed cross-coupling of aryl electrophiles with triethoxysilane

被引：55

作者：

Murata, Miki ^{[1
]}

Yamasaki, Hiyruki ^{[1
]}

Ueta, Tsukasa ^{[1
]}

Nagata, Masayuki ^{[1
]}

Ishikura, Masanori ^{[1
]}

Watanabe, Shinji ^{[1
]}

Masuda, Yuzuru ^{[1
]}

机构：

[1] Kitami Inst Technol, Dept Mat Sci, Kitami, Hokkaido 0908507, Japan

来源：

TETRAHEDRON | 2007年 / 63卷 / 19期

关键词：

arylsilanes; hydrosilane; silylation; rhodium catalyst;

D O I：

10.1016/j.tet.2007.02.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The general and efficient silylation of aryl halides has been developed utilizing triethoxysilane and a rhodium catalyst, The substrate scope is broad and includes ortho-, meta-, and para-substituted electron-rich and -deficient aryl iodides. In addition, the silylation of aryl bromides and fluoroalkanesulfonates proceeded in the presence of tetra-n-butylammonium iodide. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4087 / 4094

页数：8

共 57 条

[1] Palladium-catalyzed amination of aryl nonaflates
Anderson, KW
Mendez-Perez, M
Priego, J
Buchwald, SL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) : 9563 - 9573
[2] [Anonymous], TOUAGOUSEI KENKYU NE
[3] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls
Baudoin, O
Guénard, D
Guéritte, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 9268 - 9271
[4] Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis
Broutin, PE
Cerna, I
Campaniello, M
Leroux, F
Colobert, F
[J]. ORGANIC LETTERS, 2004, 6 (24) : 4419 - 4422
[5] Reactions of hydrosilanes with transition-metal complexes: Formation of stable transition-metal silyl compounds
Corey, JY
Braddock-Wilking, J
[J]. CHEMICAL REVIEWS, 1999, 99 (01) : 175 - 292
[6] Palladium-catalyzed silylation of aryl bromides leading to functionalized aryldimethylsilanols
Denmark, SE
Kallemeyn, JM
[J]. ORGANIC LETTERS, 2003, 5 (19) : 3483 - 3486
[7] Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes
Denmark, SE
Amishiro, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 6997 - 7003
[8] Hypervalent siloxane derivatives. An alternative to Stille and Suzuki couplings
DeShong, P
Handy, CJ
Mowery, ME
[J]. PURE AND APPLIED CHEMISTRY, 2000, 72 (09) : 1655 - 1658
[9] Catalytic C-H bond functionalization: Synthesis of arylsilanes by dehydrogenative transfer coupling of arenes and triethylsilane
Ezbiansky, K
Djurovich, PI
LaForest, M
Sinning, DJ
Zayes, R
Berry, DH
[J]. ORGANOMETALLICS, 1998, 17 (08) : 1455 - 1457
[10] CATIONIC TRANSITION-METAL COMPLEXES .1. SYNTHESIS AND REACTIONS OF BIS(DIENE)-RHODIUM AND BIS(DIENE)-IRIDIUM TETRAFLUOROBORATES
GREEN, M
KUC, TA
TAYLOR, SH
[J]. JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1971, (14): : 2334 - &

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