无外加光催化剂下可见光促进的可控有机反应进展

doi:10.6023/cjoc202203006

有机化学 ›› 2022, Vol. 42 ›› Issue (7): 1883-1903.DOI: 10.6023/cjoc202203006 上一篇下一篇

研究专题

无外加光催化剂下可见光促进的可控有机反应进展

高润烨^a^,^b, 左玲玲^b^,^e^,^*(), 王芳^b^,^e, 李传莹^a^,^*(), 蒋华江^b, 李品华^c^,^d^,^*(), 王磊^b^,^c^,^e^,^*()

^a浙江理工大学化学系杭州 310018
^b台州学院高等研究院药学院和医化学院台州 318000
^c淮北师范大学绿色和精准合成化学教育部重点实验室台州 235000
^d安徽工程大学化学与环境工程学院芜湖 241000
^e中国科学院上海有机化学研究所金属有机国家重点实验室上海 200032

收稿日期:2022-03-01 修回日期:2022-03-26 发布日期:2022-08-09
通讯作者: 左玲玲, 李传莹, 李品华, 王磊
基金资助:
国家自然科学基金(22071171); 浙江省自然科学基金(LZ22B020003); 浙江省万人计划(2019R51012)

Recent Advances in Controllable Organic Reactions Induced by Visible Light without External Photocatalyst

Runye Gao^a^,^b, Lingling Zuo^b^,^e(), Fang Wang^b^,^e, Chuanying Li^a(), Huajiang Jiang^b, Pinhua Li^c^,^d(), Lei Wang^b^,^c^,^e()

^aDepartment of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018
^bAdvanced Research Institute, Department of Pharmacy and Chemistry, Taizhou University, Taizhou, Zhejiang 318000
^cKey Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Huaibei Normal University, Huabei, Anhui 235000
^dCollege of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000
^eState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-03-01 Revised:2022-03-26 Published:2022-08-09
Contact: Lingling Zuo, Chuanying Li, Pinhua Li, Lei Wang
Supported by:
National Natural Science Foundation of China(22071171); Natural Science Foundation of Zhejiang Province(LZ22B020003); Ten Thousand People Plan of Zhejiang Province(2019R51012)

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摘要/Abstract

在无外加光敏化剂条件下, 实现近紫外及可见光诱导的有机合成反应, 引起了人们的极大兴趣和关注. 由于在反应体系中不需外加任何光敏化剂, 使得反应体系更加简单易行, 也为可见光诱导的有机反应预示了未来发展方向. 综述了近年来在外加无光敏化剂条件下, 可见光促进的有机合成反应. 包括: 底物/产物为吸光物质实现的有机光合成反应; 电子给体受体(EDA)配合物为吸光物质实现的有机光合成反应; 可见光照射弱化学键的均裂实现的有机光合成反应; 其它无外加光催化剂体系实现的有机光合成反应.

关键词: 有机合成, 有机光合成, 无外加光催化剂体系, 可见光诱导有机转化, 绿色合成

Near-ultraviolet and visible light-induced organic synthesis without photosensitizer has attracted much attention for the organic chemists. Since no photosensitizer is needed in the reaction, it makes the reaction system more simple and feasible, and indicates the future development direction for visible-light-induced organic transformations. Visible-light-promoted organic synthesis without photosensitizer is reviewed in this paper. It covers organic photosyntheses in which the substrate/product as a light-absorbing substance, the electron donor acceptor (EDA) complex as a light-absorbing substance, and the homolysis of weak covalent chemical bonds under the visible-light irradiation conditions. Moreover, other organic photosynthetic reactions without external photocatalyst are also discussed.

Key words: organic synthesis, organic photosynthesis, catalytic system without external photocatalyst, visible-light-induced organic transformations, green synthesis

引用此文

高润烨, 左玲玲, 王芳, 李传莹, 蒋华江, 李品华, 王磊. 无外加光催化剂下可见光促进的可控有机反应进展[J]. 有机化学, 2022, 42(7): 1883-1903.

Runye Gao, Lingling Zuo, Fang Wang, Chuanying Li, Huajiang Jiang, Pinhua Li, Lei Wang. Recent Advances in Controllable Organic Reactions Induced by Visible Light without External Photocatalyst[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1883-1903.

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图/表 42

图1. 底物和产物的吸收光谱

Figure 1. Absorption spectra of the representative substrate and product

图式1. 均相光催化机理

Scheme 1. Mechanisms of homogeneous photocatalysis

图式2. N-烷基/N-丙炔基苯胺与氧气的氧化甲酰化反应

Scheme 2. Oxidative formylation of N,N-dimethylanilines and N-alkyl-N-(prop-2-yn-1-yl)anilines with O2

图式3. 底物扩展范围

Scheme 3. Extended substrate scope

图式4. N,N-二甲基苯胺的氧化机理

Scheme 4. Oxidative mechanism of N,N-dimethylaniline

图式5. 8-氨基喹啉类化合物与CF3SO2Na选择性三氟甲基化反应和反应机理

Scheme 5. Trifluoromethylation of 8-aminoquinolines in the C5-position with CF3SO2Na and reaction mechanism

图式6. 水介质中烯炔酮与亚磺酸的自由基串联环反应

Scheme 6. Free radical tandem reaction of enynones and sulfonic acids in aqueous media

图式7. 可见光促进亚磺酸与N-炔丙基芳胺的自由基加成/环化/氧化串联反应

Scheme 7. Visible-light-induced sequence radical addition/cyclization/oxidation reaction of sulfonic acids and N-propargyl arylamines

图式8. 光诱导苯乙烯与三氟甲基亚磺酸钠的氧化三氟甲基化反应和建议机理

Scheme 8. Photoinduced oxidative trifluoromethylation of styrenes with CF3SO2Na and proposed mechanism

图式9. 可见光照射从苯乙烯合成α-碘代苯乙酮

Scheme 9. The synthesis of α-iodoacetophenones from styrenes under visible-light irradiation conditions

图式10. 钯催化/光协同催化N-取代苯胺与CF3SO2Na的邻位三氟甲基化反应和反应机理

Scheme 10. Visible-light-induced Pd-catalyzed ortho-trifluoro- methylation of acetanilides with CF3SO2Na and plausible mechanism

图式11. 可见光促进的喹喔啉-2(1H)-酮和唑类化合物的C—N偶联反应

Scheme 11. Visible-light photoredox catalyzed C—N coupling of quinoxaline-2(1H)-ones with azoles

图式12. 可见光驱动含氰基的1,5-烯炔与TMSN3和NIS/ NCS/NBS卤化环化反应

Scheme 12. Photo-driven haloazidation cyclization of 1,5-enynes having cyano groups with TMSN3 and NIS/NCS/NBS

图式13. 可见光催化的喹喔啉-2(1H)-酮C3-位二氟芳基甲基化反应

Scheme 13. Photoinitiated C3-difluoroaryl- methylation of quinoxalin-2(1H)-ones

图式14. 太阳光促进芳基偶氮与芳炔的[3+2]环加成反应和反应机理

Scheme 14. Sunlight-mediated [3+2] cycloaddition of azobenzenes with arynes and the possible reaction mechanism

图式15. 邻位辅助基团策略的[2+2]环加成反应

Scheme 15. [2+2] Cycloaddition based on neighboring group assistance strategy

图式17. [2+2]自环加成反应

Scheme 17. Homo-[2+2] photocycloaddition of the substrates

图式18. [2+2]交叉环加成反应吉布斯自由能

Scheme 18. Gibbs energy (in kJ•mol–1) for the crossed-[2+2]-cycloaddition

图式19. 反应机理

Scheme 19. Reaction mechanism

图式20. 太阳光辐照EDA配合物驱动醛与卤代烷的不对称α-烷基化反应和不对称催化机理

Scheme 20. Sunlight-irradiated and EDA-driven asymmetric α-alkylation of aldehydes with alkyl halides and asymmetric catalytic mechanism

图式21. 光照EDA络合物驱动亚磺酸、炔烃和异腈的三分子的自由基加成环化反应及EDA吸收光谱

Scheme 21. EDA-complex-induced three component radical addition/cyclization of isocyanides, alkynes and sulfinic acids by visible-light irradiation and EDA absorption spectra

图式22. 光照EDA络合物驱动亚磺酸、炔烃和异腈的反应机理

Scheme 22. Photo-driven reaction mechanism of isocyanides, alkynes, and sulfinic acids by EDA complex

图式23. 可见光驱动EDA催化烯酰胺与亚磺酸的加成环化反应和烯砜的氢化反应及EDA吸收光谱

Scheme 23. Visible-light-driven and EDA catalyzed cyclization of acrylamides and sulfonic acids and hydrogenation of vinylsulfones and their EDA absorption spectra

图式24. 可见光诱导的脱羧环化/氢化串联反应

Scheme 24. Visible-light-induced decarboxylative cyclization/hydrogenation cascade reaction

图式25. 可见光诱导喹诺沙林-2(1H)-酮与烷基硼酸的化学选择性反应及EDA络合物(I)的生成

Scheme 25. Visible-light-induced chemoselective reactions of quinoxalin-2(1H)-ones with alkylboronic acids and the formation of EDA complex (I)

图式26. 太阳光驱动的高碘试剂催化的α-酮酸与溴乙炔的脱羧炔化反应

Scheme 26. Sunlight-driven decarboxylative alkynylation of α-keto acids with bromoacetylenes

图式27. 溴乙炔与α-酮酸的脱羧炔化反应机理

Scheme 27. Proposed mechanism for the decarboxylative alkynylation of α-keto acids with bromoacetylenes

图式28. 烯酰胺与酮酸的脱羧串联环化反应

Scheme 28. Decarboxylative tandem cyclization reaction of acrylamides with α-oxocarboxylic acids

图式29. α-羰基羧酸与苯基丙炔酸酯类化合物的脱羧酰化环化反应

Scheme 29. Decarboxylative acylarylation of phenyl propiolates with α-oxocarboxylic acids

图式30. 可见光促进的炔溴和芳胺的酰胺化反应及反应机理

Scheme 30. Visible-light-induced amidation of bromoalkynes with anilines and reaction mechanism

图式31. 可见光照射溴炔与醇的可控化学选择性偶联反应制备炔丙醇和α-酮酸酯

Scheme 31. Visible-light-irradiated controllable chemoselectivity in the coupling of bromoalkynes with alcohols to propargyl alcohols and α-ketoesters

图式32. 可见光诱导炔溴与醚类化合物的α[C(sp3)—H]-炔基化反应

Scheme 32. Visible-light-induced alkynylation of α[C(sp3)—H] of ethers with alkynyl bromides

图式33. 可见光照射下巯基自由基催化氧气氧化二芳基炔制备1,2-二酮类化合物及底物的吸收光谱

Scheme 33. Visible-light irradiated thiyl radical catalyzed oxidation of diarylalkynes to α-diketones by molecular oxygen and the spectrum of the substrate

图式34. 可见光促进的二硫/硒醚与2-炔基苯胺的氧化环化反应

Scheme 34. Visible-light-induced oxidative cyclization of 2-alkynylanilines with disulfides and diselenides

图式35. 可见光诱导溴炔与2,2'-二氨基二芳基二硫醚的Csp—SII偶联反应及反应机理

Scheme 35. Visible-light-induced Csp—SII coupling between bromoalkynes and 2,2'-diaminodiaryldisulfides and plausible reaction mechanism

图式36. 可见光诱导苯乙烯的羟基硫化和烷氧基硫化反应及反应机理

Scheme 36. Visible-light-induced hydroxysulfurization and alkoxysulfurization of styrenes and the reaction mechanism

图式37. 可见光照射丙炔酸酯经自由基环化生成香豆素及反应机理

Scheme 37. Photoinduced cyclization of propargyl esters to coumarins and the proposed mechanism

图式38. 丙炔酸苯酯和苯乙炔的光诱导串联环化合成萘并[2,1-c]香豆素

Scheme 38. Visible-light-induced tandem cyclization of alkynoates and phenylacetylenes to naphtho[2,1-c]coumarins

图式39. α-羰基酸和炔烃的光化学合成3-羟基菲[9,10-c]呋喃-1(3H)-酮和反应机理

Scheme 39. Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones from α-keto acids and alkynes and the proposed mechanism

图式40. 光诱导/铁催化N-芳基丙烯酰胺和二甲基亚砜的甲基化环化反应

Scheme 40. Visible-light-induced/iron-catalyzed methylation of N-arylacrylamides with DMSO

图式41. 偶氮苯与DMSO的N-甲基化和N-磺酰化反应

Scheme 41. Photoinduced N-methylation and N-sulfonylation of azobenzenes with DMSO

图式42. 可见光诱导邻(烯丙氧基)苯甲醛和芳亚磺酸的自由基环化反应和反应机理

Scheme 42. Visible-light-induced radical cyclization of arylsulfinic acids with o-(allyloxy)arylaldehydes and the mechanism

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无外加光催化剂下可见光促进的可控有机反应进展

Recent Advances in Controllable Organic Reactions Induced by Visible Light without External Photocatalyst

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