Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)-C(sp2) Bond-Forming Reaction

被引：74

作者：

Trofimov, Boris A. ^{[1
]}

Schmidt, Elena Yu. ^{[1
]}

Ushakov, Igor' A. ^{[1
]}

Zorina, Nadezhda V. ^{[1
]}

Skital'tseva, Elena V. ^{[1
]}

Protsuk, Nadezhda I. ^{[1
]}

Mikhaleva, Al'bina I. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 28期

关键词：

alkynes; C-C bond formation; ketones; superbases; vinylation; C-H BONDS; ACTIVE METHINE COMPOUNDS; 1,3-DICARBONYL COMPOUNDS; ACETYLENE; ADJACENT;

D O I：

10.1002/chem.201000227

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkylaryl- and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 degrees C, 1 h) to give regio- and stereoselectively the (E)-beta-gamma-ethylenic ketones ((E)-3-buten-1-ones) in 61-84% yields and with approximately 100% stereoselectivity. This vinylation represents a new C(sp(3))-C(sp(2)) bond-forming reaction of high synthetic potential.

引用

页码：8516 / 8521

页数：6

共 32 条

[1]

BUKOWSKA M, 1983, POL J CHEM, V57, P867

[2] Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].