Palladium/Me3SiOTf-catalyzed bis-silylation of α,β-unsaturated carbonyl compounds without involving oxidative addition of disilane

被引：60

作者：

Ogoshi, S ^{[1
]}

Tomiyasu, S ^{[1
]}

Morita, M ^{[1
]}

Kurosawa, H ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 39期

关键词：

D O I：

10.1021/ja0272944

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of a catalytic amount of Me3SiOTf and palladium(0), the addition of disilane to α,β-unsaturated carbonyl compounds proceeds under very mild conditions via η3-siloxyallylpalladium generated by the reaction of enone, enal, or aromatic aldehyde with palladium and Me3SiOTf. Copyright © 2002 American Chemical Society.

引用

页码：11598 / 11599

页数：2

共 22 条

[1] THE CONJUGATE ADDITION OF A SILYL GROUP TO ENONES AND ITS REMOVAL WITH COPPER(II) BROMIDE - A PROTECTING GROUP FOR THE ALPHA-BETA-UNSATURATION OF ALPHA-BETA-UNSATURATED KETONES [J].

AGER, DJ ;

FLEMING, I ;

PATEL, SK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2520-2526

[2] SILICON-BASED PROTECTING GROUP FOR ALPHA-BETA-UNSATURATION OF ALPHA-BETA-UNSATURATED KETONES [J].

AGER, DJ ;

FLEMING, I .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (04) :177-178

[3] STEREOSELECTIVE ALKENE SYNTHESIS VIA (ALPHA-CHLOROALKYL)DIMETHYLPHENYLSILANES AND ALPHA-DIMETHYLPHENYLSILYL KETONES [J].

BARRETT, AGM ;

HILL, JM ;

WALLACE, EM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :386-389

[4] EFFECT OF A BETA-SILYL GROUP ON THE REGIOCHEMISTRY OF ENOLIZATION OF KETONES [J].

ENGEL, W ;

FLEMING, I ;

SMITHERS, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09) :1637-1641

[5] Conjugate addition of silyl groups to beta-unsubstituted enones, & Si-to-OH conversion: A synthesis of (+/-)-lavandulol [J].

Fleming, I ;

Lee, D .

TETRAHEDRON LETTERS, 1996, 37 (38) :6929-6930

[6] NICKEL-CATALYZED, CHLOROTRIALKYLSILANE-ASSISTED CONJUGATE ADDITION OF ALKENYLTRIBUTYLTIN REAGENTS TO ALPHA,BETA-UNSATURATED ALDEHYDES - EVIDENCE FOR A [1-((TRIALKYLSILYL)OXY)ALLYL]NICKEL(II) MECHANISM [J].

GRISSO, BA ;

JOHNSON, JR ;

MACKENZIE, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5160-5165

[7] PALLADIUM-CATALYZED ASYMMETRIC 1,4-DISILYLATION OF ALPHA,BETA-UNSATURATED KETONES - CATALYTIC ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY KETONES [J].

HAYASHI, T ;

MATSUMOTO, Y ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) :5579-5581

[8] Studies on organosilicon chemistry.: Part 145.: New method for introduction of a silyl group into α,β-enones using a disilane catalyzed by a copper(I) salt [J].

Ito, H ;

Ishizuka, T ;

Tateiwa, J ;

Sonoda, M ;

Hosomi, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (43) :11196-11197

[9] A PRACTICAL REVERSED-POLARITY ALTERNATIVE TO ORGANOCUPRATE CONJUGATE ADDITION CHEMISTRY - HALOCARBON COUPLING REACTIONS OF ENAL-DERIVED AND ENONE-DERIVED ALLYLNICKEL REAGENTS [J].

JOHNSON, JR ;

TULLY, PS ;

MACKENZIE, PB ;

SABAT, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6172-6177

[10] PALLADIUM-CATALYZED DISILANE METATHESIS REACTIONS OF 1,2-DISILACYCLOBUTANES [J].

KUSUKAWA, T ;

KABE, Y ;

NESTLER, B ;

ANDO, W .

ORGANOMETALLICS, 1995, 14 (05) :2556-2564

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