有机硒参与的硒环化反应研究进展

doi:10.6023/cjoc202008009

有机化学 ›› 2021, Vol. 41 ›› Issue (3): 1012-1030.DOI: 10.6023/cjoc202008009 上一篇下一篇

综述与进展

有机硒参与的硒环化反应研究进展

许颖¹, 李晨¹, 孟建萍¹, 黄玉玲¹, 付纪源¹, 刘冰¹, 刘颖杰¹, 陈宁¹^,^*()

1 哈尔滨商业大学药学院哈尔滨 150076

收稿日期:2020-08-08 修回日期:2020-09-09 发布日期:2020-09-30
通讯作者: 陈宁
基金资助:
黑龙江省自然科学基金优秀青年项目(YQ2019B004); 黑龙江省自然基金面上目(H2017001); 哈尔滨商业大学青年创新人才(2016QN056); 哈尔滨商业大学青年创新人才(2019CX38); 哈尔滨商业大学青年后备人才(2019CX36); 黑龙江省自然基金联合引导(LH2020H068); 黑龙江省自然基金联合引导(LH2020H070)

Recent Progress in the Selenocyclization Reactions with Organic Selenides

Ying Xu¹, Chen Li¹, Jianping Meng¹, Yuling Huang¹, Jiyuan Fu¹, Bing Liu¹, Yingjie Liu¹, Ning Chen¹^,^*()

1 School of Pharmacy, Harbin University of Commerce, Harbin 150076

Received:2020-08-08 Revised:2020-09-09 Published:2020-09-30
Contact: Ning Chen
About author:
* Corresponding author. E-mail: liuyj691@nenu.edu.cn
Supported by:
Outstanding Youth Project of Natural Science Foundation of Heilongjiang Province(YQ2019B004); General Project of Natural Foundation of Heilongjiang Province(H2017001); Youth Innovation Talent Project of Harbin University of Commerce(2016QN056); Youth Innovation Talent Project of Harbin University of Commerce(2019CX38); Youth Reserve Talent Program of Harbin University of Commerce(2019CX36); Natural Foundation Co-pilot Project of Heilongjiang Province(LH2020H068); Natural Foundation Co-pilot Project of Heilongjiang Province(LH2020H070)

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摘要/Abstract

有机硒化物是一类重要的分子, 在药物、农用化学品、有机材料以及催化等领域有着广泛的应用, 在有机分子中引入硒原子在合成化学中具有重要意义. 杂环化合物是构成多种生物活性分子的重要骨架, 因此, 合成含硒杂环衍生物的研究备受关注. 分别描述了近年来快速发展的金属催化、电化学驱动、可见光驱动、有机分子催化以及其它类型的硒环化反应, 并对部分反应的适用范围和机理进行了讨论.

关键词: 有机硒化物, 杂环化合物, 硒环化, 催化

Organic selenides are a kind of important molecules, which are widely used in medicine, agricultural chemicals, organic materials and catalysis, the introduction of selenium atom into organic molecules is of great significance in the synthetic chemistry. Heterocyclic compounds are key skeletons involved in a variety of bioactive molecules, therefore, the development of new methods for the synthesis of selenium-containing heterocyclic derivatives has attracted much attentions. The recent progress in this rapidly growing area, including metal catalysis, electrochemical catalysis, visible-light catalysis, organocatalysis, and other selenocyclization types, is highlighted with an emphasis on the scope and the mechanisms of these different reactions.

Key words: organic selenide, heterocyclic compound, selenocyclization, catalysis

引用此文

许颖, 李晨, 孟建萍, 黄玉玲, 付纪源, 刘冰, 刘颖杰, 陈宁. 有机硒参与的硒环化反应研究进展[J]. 有机化学, 2021, 41(3): 1012-1030.

Ying Xu, Chen Li, Jianping Meng, Yuling Huang, Jiyuan Fu, Bing Liu, Yingjie Liu, Ning Chen. Recent Progress in the Selenocyclization Reactions with Organic Selenides[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1012-1030.

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图/表 57

图1. 含硒的杂环生物活性分子

Figure 1. Selenium-containing heterocyclic bioactive molecules

图式1. CuI催化硒烯炔和碲烯炔的环化

Scheme 1. CuI catalyzed selenoenyne cyclization and telluroenyne cyclization

图式2. 钯催化炔基苯酚衍生物环化

Scheme 2. Palladium catalyzed cyclization of alkynylphenol derivatives

图式3. 铁(III)催化炔基茴香醚的环化反应

Scheme 3. Iron(III) catalyzed cyclization of anisoles

图式4. CuI催化2-炔基苯胺的环化

Scheme 4. CuI catalyzed cyclization of 2-alkynylanilines

图式5. 铜(II)催化高炔丙基硒醚的环化

Scheme 5. Copper(II) catalyzed cyclization of high propargyl selenide

图式6. 铁盐催化芳基丙酸酯和芳基丙酰胺的环化

Scheme 6. Cyclization of arylpropionates and arylpropionamides catalyzed by iron salt

图式7. 铁盐催化芳基丙酸酯和芳基丙酰胺的环化的可能机理

Scheme 7. Proposed mechanism of arylpropionates or arylpropionamides cyclization catalyzed by iron salt

图式8. CuO催化1,3-二烯基溴化物的环化

Scheme 8. CuO catalyzed cyclization of 1,3-diene bromide

图式9. CuO催化1,3-二烯基二溴化物的环化

Scheme 9. CuO catalyzed cyclization of 1,3-diene dibromides

图式10. 铜催化官能化氮化物的环化

Scheme 10. Cyclization of functionalized nitrides catalyzed by copper

图式11. 铁(III)催化芳基炔醇的环化

Scheme 11. Iron(III) catalyzed cyclization of arylalkynol

图式12. 铜(I)催化亲代硒化试剂合成三唑

Scheme 12. Synthesis of triazole by copper(I) catalyzed parent selenide

图式13. 铜(I)催化合成5-硒基-1,2,3-三唑

Scheme 13. Copper(I) promoted formation of 1,2,3-triazoles

图式14. 铜(I)催化生成1,2,3-三唑的可能机理

Scheme 14. Possible mechanism of copper(I) promoted formation of 1,2,3-triazoles

图式15. 铜(I)催化形成吲哚嗪

Scheme 15. Copper(I) catalyzed formation of indolizines

图式16. CuI催化炔基苯酚的环化

Scheme 16. CuI catalyzed cyclization of alkynylphenol

图式17. 铜催化炔丙醇的环化

Scheme 17. Copper catalyzed cyclization of propargyl alcohol

图式18. 乙酸铜(II)促进1,2,3-三唑的生成

Scheme 18. Copper(II) acetate-promoted formation of 1,2,3- triazoles

图式19. 乙酸铜(II)促进1,2,3-三唑的生成的机理

Scheme 19. Mechanism of copper(II) acetate-promoted formation of 1,2,3-triazoles

图式20. AgNO2催化炔基茴香醚的环化

Scheme 20. AgNO2 catalyzed cyclization of anisole

图式21. 自由基串联环化的可能途径

Scheme 21. Possible way of free radical cascade cyclization

图式22. 铜催化烯烃的硒二氟甲基化反应

Scheme 22. Copper-catalyzed selenodifluoromethylation of alkenes

图式23. 硒二氟甲基化反应的可能机理

Scheme 23. Proposed mechanism of selenodifluoromethylation

图式24. 铜催化β,γ-不饱和烯基腙和二苯基二硒醚的硒胺基化反应

Scheme 24. Copper-catalyzed sulfenoamination of β,γ-unsa- turated hydrazones with diphenyl diselenide

图式25. Pd(OAc)2/CuI催化的二溴乙烯基)胺与二硒醚的环化

Scheme 25. Cyclization of dibromovinyl amine and diselenide catalyzed by Pd(OAc)2/CuI

图式26. 光诱导促进烯烃环化

Scheme 26. Light-induced promotion of olefins cyclization

图式27. 光诱导促进硒环化

Scheme 27. Photoinduced promotion of selenium cyclization

图式28. 蓝光下曙红Y存在下形成螺环化合物

Scheme 28. Formation of spiro-compounds in the presence of eosyn Y under blue light

图式29. 光催化合成苯并硒基苯类化合物

Scheme 29. Photocatalytic synthesis of benzoselenylbenzenes

图式30. 光诱导促进合成三烯酮

Scheme 30. Photo-induced synthesis of triketene

图式31. 光诱导促进合成三烯酮的机理

Scheme 31. Mechanism of photo-induced synthesis of triketene

图式32. 光诱导的炔系环己二烯酮与二硒醚环化

Scheme 32. Photoinduced cyclization of acetylenic cyclohexadienones and diselenides

图式33. 光诱导的炔系环己二烯酮与硒环化的机理

Scheme 33. Mechanism of photoinduced cyclization of acetylenic cyclohexadienone and selenium

图式34. 光催化烯烃与二硒醚的脱氢环化

Scheme 34. Photocatalytic dehydrogenation and cyclization of olefins and selenium compounds

图式35. 可能的机理

Scheme 35. Possible mechanism

图式36. 电化学合成二氢呋喃

Scheme 36. Electrochemical synthesis of dihydrofuran

图式37. 电化学合成噁唑啉

Scheme 37. Electrochemical synthesis of oxazoline

图式38. 电化学合成二氢呋喃和噁唑啉的可能机理

Scheme 38. Possible mechanism electrochemical synthesis of dihydrofuran and oxazoline

图式39. 电化学合成硒化噁唑啉和异噁唑啉衍生物

Scheme 39. Electrochemical synthesis of selenide oxazoline and isoxazoline derivatives

图式40. 电化学合成香豆素和喹啉酮类化合物

Scheme 40. Electrochemical synthesis of coumarin and quinolinone compounds

图式41. 电化学合成香豆素和喹啉酮类化合物的可能机理

Scheme 41. Possible mechanism electrochemical synthesis of coumarin and quinolinone compounds

图式42. 电化学合成螺环[4.5]三烯酮

Scheme 42. Electrochemical synthesis of spiro[4.5]trienones

图式43. 螺[4.5]三烯酮的电化学合成机理

Scheme 43. Mechanism for electrochemical synthesis of spiro- [4.5]trienones

图式44. 电化学合成含硒噻唑啉

Scheme 44. Electrochemical synthesis of selenium-containing thiazoline

图式45. 噻唑啉的电化学合成机理

Scheme 45. Mechanism for the electrochemical synthesis of thiazoline

图式46. 炔烃与硒的亲电环化

Scheme 46. Electrophilic cyclization of alkynes and selenium

图式47. 环丙醛的硒环化

Scheme 47. Selenium cyclization of cyclopropaldehyde

图式48. 炔烃化合物与碘的亲电环化

Scheme 48. Electrophilic cyclization of alkyne compounds with iodine

图式49. 碘催化甲磺酰基苯胺与二苯二硒醚的环化

Scheme 49. Iodine catalyzed cyclization of methanesulphonylaniline and diphenylselenide

图式50. 碘催化丙炔醇的环化

Scheme 50. Cyclization of propargyl alcohol catalyzed by iodine

图式51. DABCO催化烯胺的环化

Scheme 51. Cyclization of enamine catalyzed by 1,4-diaza- bicyclo[2.2.2] octane

图式52. 炔烃化合物与硒的环化

Scheme 52. Cyclization of alkyne compounds with selenium

图式53. 炔丙基芳基醚与二芳基二硒醚环化

Scheme 53. Cyclization of propargyl aryl ether and diaryl diselenide

图式54. 炔丙基芳基醚与二芳基二硒醚环化可能的机理

Scheme 54. Proposed mechanism cyclization of propargyl aryl ether and diaryl diselenide

图式55. 环化反应合成三烯酮

Scheme 55. Synthesis of triketene by cyclization

图式56. 合成三烯酮的可能机理

Scheme 56. Possible mechanism of synthesis of triketene

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有机硒参与的硒环化反应研究进展

Recent Progress in the Selenocyclization Reactions with Organic Selenides

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