光催化下二芳基碘鎓盐参与的自由基芳基化反应研究进展

doi:10.6023/cjoc202106006

摘要/Abstract

二芳基高价碘盐在有机合成中被广泛应用. 总结了二芳基高价碘试剂在可见光诱导的自由基芳基化反应中的研究进展. 根据反应类型, 分为碳碳键的形成、碳硫键的形成和碳膦键的形成三部分进行综述.

Diaryliodonium salts have been widely applied in organic transformations. According to the reaction type, the use of diaryliodonium salts in visible light induced arylation reactions is summarized from the following three parts: C—C bond formation, C—S bond formation and C—P bond formation.

Key words: diaryliodonium salt, visible light, radical reaction

引用此文

孙媛媛, 宋敬城, 秦启学, 张恩选, 韩晴晴, 杨少慧, 王祖利, 岳姗, 董道青. 光催化下二芳基碘鎓盐参与的自由基芳基化反应研究进展[J]. 有机化学, 2021, 41(12): 4651-4660.

Yuanyuan Sun, Jingcheng Song, Qixue Qin, Enxuan Zhang, Qingqing Han, Shaohui Yang, Zuli Wang, Shan Yue, Daoqing Dong. Recent Progress in Radical Arylation Reaction with Diaryliodonium Salts under Photocatalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4651-4660.

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图/表 18

Scheme 1. Reactions triggered by diaryliodonium salts

Scheme 2. Arylation of arenes and heteroarenes

Scheme 3. Arylation of quinoline and pyridine N-oxides

Scheme 4. Arylation of vinyl arenes with diaryliodonium salts

Scheme 5. Oxyarylation reaction with diaryliodonium salts

Scheme 6. Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides

Scheme 7. Proposed mechanism for the synthesis of isoquinolines

Scheme 8. Photocatalytic acylarylation of unactivated alkenes

Scheme 9. Consecutive domino arylation of ortho-hydroxyaryl enaminones

Scheme 10. Three-component synthesis of N-aminosulfon-amides with sulfur dioxidesurrogates

Scheme 11. Three-component coupling of thiols, iodonium salts and SO2

Scheme 12. Sulfonylation of various imidazopyridines under visible-light

Scheme 13. Sulfoxidation and sulfenylation with organic thiosulfate salts

Scheme 14. Three-component synthesis of 3-arylsulfonylquinoline derivatives

Scheme 15. Visible-light mediated cyclization reported by Manolikakes group

Scheme 16. Visible light mediated access to azaspiro[4,5]-trienones with diaryiodonium salts

Scheme 17. Reaction of diaryliodonium salts with phosphites

Scheme 18. Arylation of tertiary phosphines with aryl(mesityl)- iodonium triflates.

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