Alkynes as synthetic equivalents to stabilized wittig reagents:: Intra- and intermolecular carbonyl olefinations catalyzed by Ag(I), BF3, and HBF4

被引：157

作者：

Rhee, JU ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 12期

关键词：

D O I：

10.1021/ol050838x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4) and Lewis acid (BF3) catalyst systems is made. Notably, intermolecular coupling proceeds stereoselectively to afford the corresponding trisubstituted enones as single geometrical isomers. This transformation represents a completely atom economical alternative to the use of stabilized Wittig reagents in carbonyl olefination and may be viewed as a formal alkyne-carbonyl metathesis.

引用

页码：2493 / 2495

页数：3

共 48 条

[41] Organometallic compounds of copper and silver.: 15.: Synthesis and structure of alkynesilver(I) complexes of the [AgX(η2-cycloalkyne)] type (X = NO3, NO2, CN, BF4, OSO2CF3, CH3COO, CF3COO, hexafluoroacetyl acetonate; cycloalkyne = 3,3,6,6-tetramethyl-1-thia-4-cycloheptyne and 3,3,6,6-tetramethyl-1-thia-4-cycloheptyne-1,1-dioxide) [J].