Tri- and Tetrasubstituted Functionalized Vinyl Sulfides by Radical Allylation

被引：13
|
作者：
Debien, Laurent [1 ]
Braun, Marie-Gabrielle [1 ]
Quiclet-Sire, Beatrice [1 ]
Zard, Samir Z. [1 ]
机构：
[1] Ecole Polytech, Synth Organ Lab, CNRS, UMR 7652, F-91128 Palaiseau, France
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 24期
关键词：
INTRAMOLECULAR REACTIONS; REDUCTIVE LITHIATION; ALKENYL SULFIDES; ENOL THIOETHERS; CYCLIZATION; HYDROTHIOLATION; ALKYNES; THIOLS; ARYL; AMIDOALKYLATION;
D O I：
10.1021/ol403103u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.
引用
收藏
页码：6250 / 6253
页数：4
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