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

doi:10.6023/cjoc202203006

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 1883-1903.DOI: 10.6023/cjoc202203006 Previous Articles Next Articles

ACCOUNT

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)

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

Cite this article

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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Fig. & Tab. 42

Figure 1. Absorption spectra of the representative substrate and product

Scheme 1. Mechanisms of homogeneous photocatalysis

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

Scheme 3. Extended substrate scope

Scheme 4. Oxidative mechanism of N,N-dimethylaniline

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 19. Reaction mechanism

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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