炔烃的自由基砜基化反应研究进展

doi:10.6023/cjoc202210015

摘要/Abstract

近年来, 利用亚磺酸钠、磺酰肼、亚磺酸、磺酰氯、二甲基亚砜(DMSO)或双(二氧化硫)-1,4-二氮杂双环[2.2.2]辛烷加合物(DABSO)为砜基源, 在光催化、电催化、金属催化和氧化体系中易形成砜自由基的特点, 由砜自由基介导炔烃的双官能化反应合成烯基砜取得了快速的发展. 按照构建C—X键的不同, 分类总结了各种反应体系, 并对存在的难点和未来发展的方向进行了展望.

关键词: 砜自由基, 炔烃, 双官能化, 自由基加成

With sodium sulfinates, sulfonyl hydrazides, sulfinic acids, sulfonyl chlorides, dimethyl sulfoxide (DMSO) or 1,4- diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate (DABSO) as the sulfonyl source, which is easily formation of sulfone radical mediated by photocatalysis, electrocatalysis, metal catalysis and oxidant systems. Direct sulfone radical initiated difunctionalization of alkynes provides an efficient pathway for the synthesis of highly functionalized vinyl sulfones. According to the construction of C—X bond, the progress of involved sulfonation method in recent years is reviewed, and the difficulties and future development of this strategy are prospected.

Key words: sulfone radical, alkyne, difunctionalization, radical addition

引用此文

马佳敏, 李姣兄, 孟千森, 曾祥华. 炔烃的自由基砜基化反应研究进展[J]. 有机化学, 2023, 43(6): 2040-2052.

Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.

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图/表 27

图1. 含烯基砜结构的分子

Figure 1. Molecules containing vinyl sulfone unit

图式1. 砜自由基介导的炔烃双官能化反应机理

Scheme 1. Sulfone radical mediated difunctionalization of alkynes

图式2. 炔烃的碘砜化反应

Scheme 2. Methods for iodo sulfonation of alkynes

图式3. 水中发生碘砜化反应

Scheme 3. Methods for iodosulfonation reaction in water

图式4. 炔烃的溴砜化反应

Scheme 4. Methods for bromosulfonation of alkynes

图式5. 合成(Z)-β-氯代烯基砜的方法

Scheme 5. Methods for synthesis of (Z)-β-chlorovinyl sulfones

图式6. 铁催化合成β-氯代烯基砜

Scheme 6. Iron-catalyzed synthesis of β-chlorovinyl sulfones

图式7. 光催化合成β-氯代烯基砜

Scheme 7. Photo-catalyzed synthesis of β-chlorovinyl sulfones

图式8. 三组分法合成β-氯代烯基砜

Scheme 8. Three-components for synthesis of β-chlorovinyl sulfones

图式9. 氢砜化炔烃

Scheme 9. Methods for hydrosulfonation of alkynes

图式10. 铜催化炔烃的氢砜化反应

Scheme 10. Copper-catalyzed hydrosulfonation of alkynes

图式11. 炔烃的氧砜基化反应

Scheme 11. Oxysulfonation of alkynes

图式12. 炔烃在水溶液中的氧砜基化反应

Scheme 12. Oxysulfonation of alkynes in water

图式13. 光或电促进炔烃的氧砜基化反应

Scheme 13. Photo or electro-promoted oxysulfonation of alkynes

图式14. 炔烃的氧砜基化反应

Scheme 14. Oxysulfonation of alkynes

图式15. 炔烃的双砜基化反应

Scheme 15. Disulfonation of alkynes

图式16. 炔烃的硫醚砜基化反应

Scheme 16. Thiosulfonation of alkynes

图式17. 炔烃的亚砜砜基化反应

Scheme 17. Sulfinosulfonation of alkynes

图式18. 炔烃的硒砜基化反应

Scheme 18. Selenosulfonation of alkynes

图式19. 光催化炔烃的硒砜基化反应

Scheme 19. Photo-catalyzed selenosulfonation of alkynes

图式20. 炔烃的胺砜基化反应

Scheme 20. Aminosulfonation of alkynes

图式21. 砜自由基介导炔烃的胺基环化反应

Scheme 21. Sulfonyl radical-promoted aminocyclization of alkynes

图式22. 炔烃的肟砜基化反应

Scheme 22. Oximosulfonation of alkynes

图式23. 炔烃的叠氮砜化反应

Scheme 23. Azidosulfonylation of alkynes

图式24. 炔烃的碳砜基化反应

Scheme 24. Carbosulfonation of alkynes

图式25. 炔烃的同碳碳砜基化反应

Scheme 25. Geminal carbosulfonation of alkynes

图式26. 光催化炔烃的环化反应

Scheme 26. Photo-catalyzed cyclization of alkynes

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