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：71
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
收藏
页码：7206 / 7211
页数：6
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