In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates,Organic Letters

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In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates
Organic Letters ( IF 4.9 ) Pub Date : 2019-05-03 00:00:00 , DOI: 10.1021/acs.orglett.9b01046
Linlin Xing ₁ , Yong Zhang ₁ , Bing Li ₁ , Yunfei Du _{1,

2}

Affiliation

The reaction of diorganyl disulfides or diselenides with PhICl₂ in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramolecular chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones in good to excellent yields under metal-free conditions.

中文翻译：

RSCl / ArSeCl的原位形成及其在邻-（1-炔基）苯甲酸酯和（Z）-2-Alken-4-yanoates合成4-硫属异氰酸酯/吡喃酮中的应用

首次发现二有机基二硫化物或二硒化物与PhICl ₂在乙腈中的反应导致原位形成有机亚磺酰氯或亚硒基氯，这使炔的区域选择性分子内硫属半乳糖基酰氧基化反应导致形成4-硫属元素基异cumarins /吡喃酮。在无金属条件下的收率好至极好。

更新日期：2019-05-03

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