Platinum oxide catalyzed hydrosilylation of unsymmetrical internal aryl alkynes under ortho-substituent regiocontrol

被引:61
作者
Hamze, A [1 ]
Provot, O [1 ]
Alami, M [1 ]
Brion, JD [1 ]
机构
[1] Univ Paris 11, Fac Pharm, CNRS, UMR 8076,BioCIS,Lab Chim Therapeut, F-92296 Chatenay Malabry, France
关键词
D O I
10.1021/ol052245s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] PtO2- and H2PtCl6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed and compared. The regioselectivity of the H-Si bond addition was found to be controlled by the ortho substituent rather than the nature of the platinum catalyst. Arylallcynes with an ortho substituent, regardless of its electronic nature, directed the silyl substituent mainly to the a-position. PtO2 proved to be a versatile and powerful catalyst compared to H2PtCl6 since it prevents the alkyne reduction.
引用
收藏
页码:5625 / 5628
页数:4
相关论文
共 34 条
[1]  
Alami M, 2002, ANGEW CHEM INT EDIT, V41, P1578, DOI 10.1002/1521-3773(20020503)41:9<1578::AID-ANIE1578>3.0.CO
[2]  
2-C
[3]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].
ALAMI, M ;
FERRI, F ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406
[4]   Radical transfer hydrosilylation/cyclization using silylated cyclohexadienes [J].
Amrein, S ;
Timmermann, A ;
Studer, A .
ORGANIC LETTERS, 2001, 3 (15) :2357-2360
[5]   Regio- and stereoselective hydrosilylation of terminal alkynes using Grubbs' first-generation olefin-metathesis catalyst [J].
Aricó, CS ;
Cox, LR .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (18) :2558-2562
[6]   Lewis acid-catalyzed trans-hydrosilylation of alkynes [J].
Asao, N ;
Sudo, T ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7654-7655
[7]  
Benkeser R. A., 1966, PURE APPL CHEM, V13, P133
[8]   STEREOCHEMISTRY OF ADDITION OF SILICOCHLOROFORM TO ACETYLENES - A COMPARISON OF CATALYST SYSTEMS [J].
BENKESER, RA ;
BURROUS, ML ;
SWISHER, JV ;
NELSON, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (21) :4385-&
[9]   VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].
BLUMENKOPF, TA ;
OVERMAN, LE .
CHEMICAL REVIEWS, 1986, 86 (05) :857-873
[10]   Hydrosilylation of alkynes catalyzed by platinum on carbon [J].
Chauhan, M ;
Hauck, BJ ;
Keller, LP ;
Boudjouk, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :1-13