Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

被引：76

作者：

Talero, Alexander Garay ^{[1
]}

Martins, Bruna Simoes ^{[1
]}

Burtoloso, Antonio C. B. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 22期

基金：

巴西圣保罗研究基金会;

关键词：

DIAZO-CARBONYL-COMPOUNDS; H INSERTION REACTIONS; SULFUR YLIDES; FORMAL SYNTHESIS; SULFONIUM; ARYLATION; BONDS; FUNCTIONALIZATION; CYCLOPROPANATION; DECOMPOSITION;

D O I：

10.1021/acs.orglett.8b03126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, mild, and versatile synthesis of the challenging alpha-aryl-beta-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible beta-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into alpha-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.

引用

页码：7206 / 7211

页数：6

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