Visible-Light-Promoted Cross-Coupling Reactions of 4-Alkyl-1,4-dihydropyridines with Thiosulfonate or Selenium Sulfonate: A Unified Approach to Sulfides, Selenides, and Sulfoxides

被引：66

作者：

Li, Jian ^{[1
,2
]}

Yang, Xin-Er ^{[1
,2
]}

Wang, Shan-Le ^{[1
,2
]}

Zhang, Long-Long ^{[1
,2
]}

Zhou, Xiao-Zhou ^{[3
]}

Wang, Shun-Yi ^{[1
,2
]}

Ji, Shun-Jun ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China

[3] Suzhou High Sch Jiangsu Prov, Suzhou 215000, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

基金：

中国国家自然科学基金;

关键词：

PHOTOREDOX CATALYSIS; DISULFIDES; ACTIVATION; ETHERS; 3-SULFENYLATION; SUBSTITUTION; PHOSPHORUS; COMPLEXES; INDOLES; ALKENES;

D O I：

10.1021/acs.orglett.0c01776

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, a visible-light-promoted cross-coupling of 4-alkyl-1,4-dihydropyridines with thio-/selenium sulfonates under transition-metal-free conditions is described. This strategy features easily available substrates, mild reaction conditions, high yields, and high chemoselectivity. A novel synthetic route for the construction of a sulfide or selenide C-sp3-S or C-sp3-Se bond under transition-metal-free conditions without an additive oxidant or base is developed. This method is well extended to the synthesis of a class of thiolated or selenylated glycosides that has not been explored before. Sulfoxides were also successfully chemoselectively observed via a facile variation of the atmosphere under photocatalyzed conditions.

引用

页码：4908 / 4913

页数：6

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