Electrochemical Stereoselective Synthesis of (Z)-Allyl Aryl Selenides and Sulfides from Baylis-Hillman Acetates

被引：2

作者：

Sun, Li ^{[1
,2
]}

Xia, Mengcan ^{[1
,2
]}

Yu, Guorui ^{[1
,2
]}

Liu, Sheng ^{[1
,2
]}

Wu, Yafei ^{[1
,2
]}

Zhao, Kun ^{[3
]}

Mao, Biming ^{[1
,2
]}

机构：

[1] Shandong First Med Univ & Shandong Acad Med Sci, Sch Pharmaceut Sci, Jinan 250117, Shandong, Peoples R China

[2] Shandong First Med Univ & Shandong Acad Med Sci, Inst Mat Med, Jinan 250117, Shandong, Peoples R China

[3] Shandong Univ, Cheeloo Coll Med, Sch Pharmaceut Sci, Key Lab Chem Biol,Minist Educ,Dept Pharmaceut, Jinan 250011, Shandong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 05期

关键词：

Electrochemistry; Morita-Baylis-Hillman Adducts; Se-Se Bond Activation; Stereoselective Synthesis; (Z)-Allyl Aryl Selenides and Sulfides; H BOND FUNCTIONALIZATION; C-S; DISULFIDES; SELENATION; CHEMISTRY;

D O I：

10.1002/adsc.202301289

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

This research presents a method for the oxidative selenylation and thiolylation of Morita-Baylis-Hillman adducts through constant-current electrolysis in an undivided cell at room temperature. The reaction enables direct production of trisubstituted (Z)-allyl aryl selenides and sulfides with yields of 27-98%. A wide variety of different functionalities are well tolerated under these reaction conditions. This strategy could be carried out on gram scale and several synthetic transformations were accomplished for the construction of other allyl selenide derivatives. Control experiments and mechanistic studies indicate a radical or an ionic addition pathway for this electrochemical transformation.

引用

页码：1152 / 1157

页数：6

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