Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light

doi:10.6023/cjoc202301006

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2269-2292.DOI: 10.6023/cjoc202301006 Previous Articles Next Articles

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可见光媒介的C—S键构建反应研究进展

吴敏^a, 刘博^b, 袁佳龙^a, 付强^a, 汪锐^a^,^*(), 娄大伟^b^,^*(), 梁福顺^c^,^*()

^a吉林化工学院石油化工学院吉林 132022
^b吉林化工学院化学与制药工程学院吉林 132022
^c辽宁大学化学院沈阳 110036

收稿日期:2023-01-07 修回日期:2023-02-20 发布日期:2023-03-30
通讯作者: 汪锐, 娄大伟, 梁福顺
基金资助:
吉林化工学院科学技术研究(2020021); 吉林化工学院重大科技(2020010); 吉林化工学院博士启动(2021016); 兴辽英才计划(XLYC1902111); 辽宁省教育厅重点(LZD202005); 吉林省产业技术研究与开发(2020C028-1); 吉林省科技发展计划(202002008JC)

Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light

Min Wu^a, Bo Liu^b, Jialong Yuan^a, Qiang Fu^a, Rui Wang^a(), Dawei Lou^b(), Fushun Liang^c()

^aInstitute of Petrochemical Technology, Jilin Institute of Chemical Technology, Jilin 132022
^bSchool of Chemistry and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, Jilin 132022
^cCollege of Chemistry, Liaoning University, Shenyang 110036

Received:2023-01-07 Revised:2023-02-20 Published:2023-03-30
Contact: Rui Wang, Dawei Lou, Fushun Liang
Supported by:
Science and Technology Research Project of Jilin Institute of Chemical Technology(2020021); Major Scientific and Technological Projects of Jilin Institute of Chemical Technology(2020010); Doctoral Start-up Foundation of Jilin Institute of Chemical Technology(2021016); Liaoning Revitalization Talents Program(XLYC1902111); Key Projects of Department of Education of Liaoning Province(LZD202005); Research and Development Project for Industrial Technology of Jilin Province(2020C028-1); Science and Technology Development of Jilin Province(202002008JC)

The construction of C—S bond is of great significance in organic synthesis, in viewing that organic compounds containing C—S bonds are widely present in various natural products, drugs and functional materials. At present, transition metal-catalyzed C—S bond formation reactions have been well developed. However, in recent years, the visible-light-mediated C—S bond formation reactions have received more and more attention due to the characteristics of milder conditions, greener and higher reactivity. According to the classification of the reaction mechanisms, the methods of C—S bond construction based on photo-mediated redox catalysis, electron donor-acceptor complexes and energy transfer are summarized and a future perspective is made.

Key words: visible-light medium, C—S bond formation, photo-redox catalysis, electron donor-acceptor complex

Cite this article

Min Wu, Bo Liu, Jialong Yuan, Qiang Fu, Rui Wang, Dawei Lou, Fushun Liang. Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2269-2292.

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Fig. & Tab. 48

Figure 1. Representative compounds containing C—S bonds

Scheme 1. Mechanism of photochemical reaction involving visible light

Scheme 2. Visible-light-induced 3-sulfenylation of N-methyl- indoles with arylsulfonyl chlorides

Scheme 3. Visible-light-mediated catalytic synthesis of 3-sul- fanylindolizines and 1,3-bis-(sulfanyl)indolizines

Scheme 4. Photoredox catalyzed anti-Markovnikov hydrothiolation of olefins

Scheme 5. Visible light-promoted redox catalysis for thiol-ene click reaction

Scheme 6. Visible-light-mediated defluorinated cross-coupling of thiols with gem-difluoroalkenes

Scheme 7. Synthsis of arylsulfides facilitated by photoredox catalysis

Scheme 8. Iridium-catalyzed cross-coupling between aryl halides and mercaptan

Scheme 9. Cercosporin-photocatalyzed C—S coupling for the selective synthesis of aryl sulfides

Scheme 10. Photocatalytic decarboxylative thiolation of carboxylic acids using fluorinated disulfides

Scheme 11. Synthesis of β-amidovinyl sulfones via visible-light photoredox catalysis

. scheme 12 Visible-light-mediated metal-free synthesis of vinyl sulfones from aryl sulfonates

Scheme 13. Photoredox-mediated synthesis of functionalized sulfoxides from terminal alkynes

Scheme 14. Direct C—H thiolation of arenes with thiophenols via aerobic visible-light catalysis

Scheme 15. Organophotoredox-catalyzed sulfurization of alkenes and alkynes

Scheme 16. Photoredox catalyzed fluorosulfonylation of olefins fluorosulfonylation of olefins

Scheme 17. Visible-light-induced direct C(sp3)—H thiocyanation of tertiary amines

Scheme 18. Visible-light-mediated C(sp3)—H thiocarbonylation for the preparation of thiolactams

Scheme 19. Aminothiolation of α?bromocinnamaldehydes to access imidazo[2,1?b]thiazoles by incorporation of two distinct photo-induced processes

Scheme 20. Visible-light-driven organophotocatalyzed multicomponent approach for tandem C(sp3)—H activation and alkylation followed by trifluoromethylthiolation

Scheme 21. Visible light-promoted C—S cross coupling between thiols and aryl halides

Scheme 22. Visible-light-driven C—S bond formation based on electron donor-acceptor excitation and hydrogen atom transfer combined system

Scheme 23. Photo-driven synthesis of C6-polyfunctionalized phenanthridines from three-component reactions of isocyanides, alkynes, and sulfinic acids by electron donor-acceptor complex

Scheme 24. Visible-light-induced intramolecular charge transfer for radical spirocyclization of indole-linked alkynyl ketones

Scheme 25. Visible-light-induced deaminative thioesterification of amino acid derived Katritzky salts via electron donor-acceptor complex formation

Scheme 26. Hydrogenation and arylsulfonylation of alkenes driven by hydrogen bond donor-acceptor complex

Scheme 27. Visible light-induced electron donor-acceptor complex formed between thiophenol and N-hydroxyphthalimide ester for C—S bond construction

Scheme 28. Synthesis of thiochroman derivatives by photoinduced electron transfer C—S cross-coupling reaction

Scheme 29. Visible light-driven electron donor-acceptor complex-induced diazobenzene tetrafluorobenzene

Scheme 30. Synthesis of β-hydroxysulfides via visible-light- driven and EDA complex-promoted hydroxysulfenylation of styrenes with heterocyclic thiols

Scheme 31. Vsible-light-promoted [3＋2] cyclization of chalcones with 2?mercaptobenz-Zimidazoles to synthesize of imidazo[2,1?b]thiazoles

Scheme 32. Photocleavage of C(non-acyl)—S bond of thioesters for regioselective pyridylthioesterification of styrenes

Scheme 33. Visible light-induced highly regioselective and stereoselective oxysulfonylation of alkynes for the synthesis of (E)?β-phen- oxy vinylsulfones

Scheme 34. Thianthrenium-enabled sulfonylation via electron donor-acceptor complex photoactivation

Scheme 35. Radical C—H sulfonylation of arenes and its application in bioactive molecules and DNA coding molecules

Scheme 36. Thenylthiation with thianthrenium salts via electron donor-acceptor photoactivation

Scheme 37. Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF

Scheme 38. Controllable sulfoxidation and sulfenylation with organic thiosulfate salts via dual electron- and energy-transfer photocatalysis

Scheme 39. Energy transfer disulfide-olefin reaction

Scheme 40. Carbon-heteroatom cross-coupling via nickel/photo dual catalysis

Scheme 41. Sulfidation and sulfonation reactions of unactivated olefins initiated by energy transfer process

Scheme 42. Photoredox/nickel dual-catalyzed thioetherification of aryl bromides

Scheme 43. Photoredox mediated nickel catalyzed cross- coupling of thiols with aryl and heteroaryl iodides

Scheme 44. Photochemical dual-catalytic synthesis of alkynyl sulfides

Scheme 45. Deoxygenative C—S bond coupling of sulfinates via nickel/photoredox dual catalysis

Scheme 46. Sulfur etherification and acylation of olefins by aldehydes and disulfides catalyzed by NHC and visible light

Scheme 47. Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis

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可见光媒介的C—S键构建反应研究进展

Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light

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