可见光媒介的C—S键构建反应研究进展

doi:10.6023/cjoc202301006

有机化学 ›› 2023, Vol. 43 ›› Issue (7): 2269-2292.DOI: 10.6023/cjoc202301006 上一篇下一篇

综述与进展

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)

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摘要/Abstract

含有C—S键的有机化合物广泛存在于各种天然产物、药物以及功能材料之中. 因此, C—S键的构建在有机合成领域有着重要意义. 目前, 基于过渡金属催化实现C—S键构建的合成方法已有广泛的应用. 然而, 近几年可见光媒介的C—S键构建反应, 由于条件更加温和、绿色以及反应活性高等特点而受到了越来越多的关注. 根据反应机制分类, 总结了近几年基于光媒介的氧化还原催化、电子给-受体复合物以及能量转移等策略实现的C—S键构建的方法, 并对其前景进行了展望.

关键词: 可见光媒介, C—S键构建, 光氧化还原催化, 电子给-受体复合物

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

引用此文

吴敏, 刘博, 袁佳龙, 付强, 汪锐, 娄大伟, 梁福顺. 可见光媒介的C—S键构建反应研究进展[J]. 有机化学, 2023, 43(7): 2269-2292.

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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图/表 48

图1. 有代表性的含有C—S键的化合物

Figure 1. Representative compounds containing C—S bonds

图式1. 可见光参与的光化学反应机制

Scheme 1. Mechanism of photochemical reaction involving visible light

图式2. 可见光诱导的芳基磺酰氯和N-甲基吲哚的3-位硫醚化反应

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

图式3. 可见光介导催化合成3-硫醚吲嗪和1,3-双(硫醚)吲嗪

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

图式4. 光氧化还原催化烯烃的反马氢硫醚化反应

Scheme 4. Photoredox catalyzed anti-Markovnikov hydrothiolation of olefins

图式5. 可见光促进的氧化还原催化实现硫醇-烯点击反应

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

图式6. 可见光介导的硫醇与偕二氟烯烃的脱氟交叉偶联

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

图式7. 光氧化还原催化芳基硫化物的合成

Scheme 7. Synthsis of arylsulfides facilitated by photoredox catalysis

图式8. 铱催化芳基卤化物和硫醇之间交叉偶联构建C—S键

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

图式9. 尾孢菌素作为光催化剂实现的C—S构建选择性合成芳基硫醚

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

图式10. 利用氟代二硫醚实现羰基羧酸的光催化脱羧硫醇化

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

图式11. 可见光光氧化还原催化合成β-酰胺基砜

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

图式12. 可见光媒介无金属催化芳基亚磺酸盐合成乙烯基砜

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

图式13. 光氧化还原催化介导的官能团化亚砜的合成

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

图式14. 在有氧环境中可见光催化芳烃和硫酚直接C—H硫醚化

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

图式15. 有机光氧化还原催化烯烃和炔烃的硫化

Scheme 15. Organophotoredox-catalyzed sulfurization of alkenes and alkynes

图式16. 光氧化还原催化烯烃的氟磺酰化

Scheme 16. Photoredox catalyzed fluorosulfonylation of olefins fluorosulfonylation of olefins

图式17. 可见光诱导叔胺直接C(sp3)—H硫氰化

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

图式18. 可见光媒介的C(sp3)—H硫代羰基化合成硫代内酰胺

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

图式19. 两种不同的光诱导过程实现的α-溴代肉桂醛的氨基硫化反应合成咪唑[2,1-b]噻唑

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

图式20. 可见光驱动有机光催化多组分串联实现C(sp3)—H活化、烷基化以及三氟甲硫基化

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

图式21. 可见光促进硫醇与芳基卤化物之间C—S交叉偶联

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

图式22. 可见光驱动基于电子给-受体复合物和氢原子转移策略实现的C—S键构建

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

图式23. 光驱动电子给-受体复合物引发的异氰化物、炔烃和亚磺酸三组分反应合成C6-多官能化菲啶类衍生物

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

图式24. 可见光诱导分子内电荷转移实现吲哚并链接炔酮类化合物的自由基螺环化反应

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

图式25. 可见光诱导给电子给-受体复合物引发氨基酸衍生物Katritzky盐的脱氨硫酯化反应

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

图式26. 氢键给-受体复合物驱动的烯烃的氢化和芳磺酰化

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

图式27. 可见光诱导的硫酚与N-羟基邻苯二甲酰亚胺酯间形成的电子给-受体复合物用于C—S键构建

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

图式28. 光诱导电子转移C—S交叉偶联反应合成硫代色满衍生物

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

图式29. 可见光驱动电子给-受体复合物诱导的重氮苯四氟硼酸盐的磺酰化

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

图式30. 可见光驱动电子给-受体复合物促进苯乙烯与杂环硫醇的羟基硫化合成β-羟基硫化物

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

图式31. 可见光促进的查尔酮与2?巯基苯并咪唑的[3＋2]环化反应合成苯并咪唑[2,1?b]噻唑

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

图式32. 光断裂硫酯的C(非酰基)—S键用于苯乙烯的区域选择性的吡啶硫酯化

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

图式33. 可见光诱导炔烃的高区域和立体选择性的氧磺酰化反应合成(E)?β-苯氧基乙烯基砜

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

图式34. 光活化电子给-受体复合物实现的噻蒽鎓盐参与的磺酰化反应

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

图式35. 芳烃自由基C—H砜基化反应及其在生物活性分子和DNA编码分子中的应用

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

图式36. 通过光活化电子给-受体复合物实现噻蒽鎓盐芳基硫醚化

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

图式37. 可见光敏化芳基磺酰叠氮化合物在四氢呋喃中实现的磺酰化环化和叠氮磺酰化环化

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

图式38. 光催化经由双电子和能量转移引发有机硫代硫酸盐可控亚砜化和硫醚化反应

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

图式39. 能量转移引发的二硫化物-烯烃反应

Scheme 39. Energy transfer disulfide-olefin reaction

图式40. 镍/光双重催化碳-杂原子交叉偶联反应

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

图式41. 能量转移引发的未活化烯烃的硫化、磺基化反应

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

图式42. 光氧化还原/镍双催化芳基溴化物的硫醚化反应

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

图式43. 光氧化还原介导的镍催化硫醇与芳基或杂芳基碘化物的交叉偶联

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

图式44. 光化学双催化合成炔基硫化物

Scheme 44. Photochemical dual-catalytic synthesis of alkynyl sulfides

图式45. 镍/光氧化还原双催化亚硫酸盐脱氧实现C—S键偶联

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

图式46. NHC和可见光催化的醛和二硫化物对烯烃的硫醚化和酰化

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

图式47. 金属光氧化还原催化氨基酸衍生物的脱羧硫化

Scheme 47. Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis

参考文献 85

[1]	Ciamician, G. Science 1912, 36, 385. pmid: 17836492
[2]	(a) Zhu, H.-Z.; Dronamraju, V.; Xie, W.; More, S. S. Med. Chem. Res. 2021, 30, 305. doi: 10.1007/s00044-020-02687-1
	(b) Wang, N.-Z.; Saidhareddy, P.; Jiang, X.-F. Nat. Prod. Rep. 2020, 37, 246. doi: 10.1039/C8NP00093J
	(c) Nicastro, H. L.; Ross, S. A.; Milner, J. A. Cancer Prev. Res. 2015, 8, 181. doi: 10.1158/1940-6207.CAPR-14-0172
	(d) Jacob, C. Nat. Prod. Rep. 2006, 23, 851. doi: 10.1039/b609523m
[3]	(a) Feng, M.-H.; Tang, B.-Q.; Liang, S. H.; Jiang, X.-F. Curr. Top. Med. Chem. 2016, 16, 1200. doi: 10.2174/1568026615666150915111741
	(b) Mustafa, M.; Winum, J. Y. Expert Opin. Drug Discovery 2022, 17, 501. doi: 10.1080/17460441.2022.2044783
[4]	(a) Boyd, D. A. Angew. Chem., Int. Ed. 2016, 55, 15486. doi: 10.1002/anie.201604615
	(b) Rahate, A. S.; Nemade, K. R.; Waghuley, S. A. Rev. Chem. Eng. 2013, 29, 471.
[5]	(a) Su, Y.; Zhou, X.-J.; He, C.-L.; Zhang, W.; Ling, X.; Xiao, X. J. Org. Chem. 2016, 81, 4981. doi: 10.1021/acs.joc.6b00475
	(b) Yang, Y.; Zhang, S.; Tang, L.; Hu, Y.-B.; Zha, Z.-G.; Wang, Z. Green Chem. 2016, 18, 2609. doi: 10.1039/C6GC00313C
	(c) Yu, J.-Q.; Ding, K.-L. Acta Chim. Sinica 2015, 73, 1223 (in Chinese). doi: 10.6023/A1512E001
	(余金权, 丁奎岭, 化学学报, 2015, 73, 1223.) doi: 10.6023/A1512E001
	(d) Sun, F.-L.; Liu, X.-M.; Chen, X.-Z.; Qian, C.; Ge, X. Chin. J. Org. Chem. 2017, 37, 2211 (in Chinese). doi: 10.6023/cjoc201703038
	(孙丰莉, 刘学民, 陈新志, 钱超, 葛新, 有机化学, 2017, 37, 2211.) doi: 10.6023/cjoc201703038
[6]	(a) Varun, B. V.; Prabhu, K. R. J. Org. Chem. 2014, 79, 9655. doi: 10.1021/jo501793q
	(b) Hostier, T.; Ferey, V.; Ricci, G.; Gomez Pardo, D.; Cossy, J. Chem. Commun. 2015, 51, 13898. doi: 10.1039/C5CC05421D
[7]	(a) Carril, M.; SanMartin, R.; Dominguez, E.; Tellitu, I. Chem.-Eur. J. 2007, 13, 5100. doi: 10.1002/(ISSN)1521-3765
	(b) Kabir, M. S.; Linn, M. L. V.; Monte, A.; Cook, J. M. Org. Lett. 2008, 10, 3363. doi: 10.1021/ol801149n
	(c) Zhu, W.; Ma, D.-W. J. Org. Chem. 2004, 70, 2696. doi: 10.1021/jo047758b
[8]	(a) Ranjit, S.; Duan, Z.; Zhang, P.; Liu, X. Org. Lett. 2010, 12, 4134. doi: 10.1021/ol101729k
	(b) Nilsson, M.; Kulonen, E.; Sunner, S.; Frank, V.; Brunvoll, J.; Bunnenberg, E.; Djerassi, C.; Records, R. Acta Chem. Scand. 1966, 20, 423. doi: 10.3891/acta.chem.scand.20-0423
	(c) Suzuki, H.; Abe, H. Tetrahedron Lett. 1995, 36, 6239. doi: 10.1016/0040-4039(95)01095-Y
	(d) Qin, Y.-C.; Peng, Q. Chin. J. Org. Chem. 2011, 31, 1169 (in Chinese).
	(秦元成, 彭强, 有机化学, 2011, 31, 1169.)
[9]	Wang, H.-B.; Wang, L.; Shang, J.-S.; Li, X.; Wang, H.-Y.; Gui, J.; Lei, A.-W. Chem. Commun. 2012, 48, 76. doi: 10.1039/C1CC16184A
[10]	Wang, P.-F.; Wang, X.-Q.; Dai, J.-J.; Feng, Y.-S.; Xu, H.-J. Org. Lett. 2014, 16, 4586. doi: 10.1021/ol502144c
[11]	Lan, M.-T.; Wu, W.-Y.; Huang, S.-H.; Luo, K.-L.; Tsai, F.-Y. RSC Adv. 2011, 1,1151.
[12]	Liu, T.-J.; Yi, C.-L.; Chan, C.-C.; Lee, C.-F. Chem.-Asian J. 2013, 8, 1029. doi: 10.1002/asia.v8.5
[13]	(a) Zhu, J.-Y.; Chen, Y.; Lin, F.; Wang, B.-S.; Chen, Z.-W.; Liu, L.-X. Org. Biomol. Chem. 2015, 13, 3711. doi: 10.1039/C4OB02586E pmid: 34306801
	(b) Brigham, C. E.; Malapit, C. A.; Lalloo, N.; Sanford, M. S. ACS Catal. 2020, 10, 8315. doi: 10.1021/acscatal.0c02950 pmid: 34306801
[14]	Tavares Junior, J.; da Silva, C. D. G.; Dos Santos, B. F.; Souza, N. S.; Oliveira, A. R. D.; Kupfer, V. L.; Rinaldi, A. W.; Domingues, N. L. C. Org. Biomol. Chem. 2019, 17, 10103. doi: 10.1039/c9ob02171j pmid: 31755516
[15]	Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2008, 74, 3189. doi: 10.1021/jo802731j
[16]	Timpa, S. D.; Pell, C. J.; Ozerov, O. V. J. Am. Chem. Soc. 2014, 136, 14772. doi: 10.1021/ja505576g
[17]	(a) Shang, R.; Liu, L. Sci. China: Chem. 2011, 54, 1670. pmid: 29178797
	(b) Ganley, J. M.; Yeung, C. S. J. Org. Chem. 2017, 82, 13557. doi: 10.1021/acs.joc.7b02712 pmid: 29178797
	(c) Becht, J. M.; Le Drian, C. J. Org. Chem. 2011, 76, 6327. doi: 10.1021/jo200344w pmid: 29178797
[18]	(a) Wimmer, A.; Konig, B. Beilstein J. Org. Chem. 2018, 14, 54. doi: 10.3762/bjoc.14.4
	(b) Gao, J.; Feng, J.; Du, D. Chem.-Asian. J. 2020, 15, 3637. doi: 10.1002/asia.v15.22
[19]	(a) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1. pmid: 20532341
	(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r pmid: 20532341
	(c) Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102. doi: 10.1039/b913880n pmid: 20532341
	(d) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148. doi: 10.1002/cptc.201700008 pmid: 20532341
	(e) Xue, D.; Song, G.-Y. Chin. J. Org. Chem. 2022, 42, 2275 (in Chinese). doi: 10.6023/cjoc202202018 pmid: 20532341
	(宋戈洋, 薛东, 有机化学, 2022, 42, 2275.) doi: 10.6023/cjoc202202018 pmid: 20532341
[20]	Yan, D.-M.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58, 378. doi: 10.1002/anie.v58.2
[21]	Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2012, 48, 11686. doi: 10.1039/c2cc36866h
[22]	Penteado, F.; Gomes, C. S.; Monzon, L. I.; Perin, G.; Silveira, C. C.; Lenardão, E. J. Eur. J. Org. Chem. 2020, 2020, 2110. doi: 10.1002/ejoc.202000162
[23]	Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2013, 78, 2046. doi: 10.1021/jo3020825
[24]	Zhao, G.-Y.; Kaur, S.; Wang, T. Org. Lett. 2017, 19, 3291. doi: 10.1021/acs.orglett.7b01441
[25]	Wang, J.-L.; Huang, B.-B.; Yang, C.; Xia, W.-J. Chem. Commun. 2019, 55, 11103. doi: 10.1039/C9CC05293C
[26]	Wang, X.; Cuny, G. D.; Noel, T. Angew. Chem., Int. Ed. 2013, 52, 7860 doi: 10.1002/anie.v52.30
[27]	Jiang, M.; Li, H.-F.; Yang, H.-J.; Fu, H. Angew. Chem., Int. Ed. 2017, 56, 874 doi: 10.1002/anie.v56.3
[28]	Li, J.; Bao, W.-H.; Zhang, Y.; Rao, Y.-J. Eur. J. Org. Chem. 2019, 2019, 7175. doi: 10.1002/ejoc.201901444
[29]	Zubkov, M. O.; Kosobokov, M. D.; Levin, V. V.; Dilman, A. D. Org. Lett. 2022, 24, 2354. doi: 10.1021/acs.orglett.2c00549
[30]	Jeremy, D. G.; Mary, A. Z.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340. doi: 10.1021/jacs.5b07770
[31]	Jiang, H.; Chen, X.-J.; Zhang, Y.; Yu, S.-Y. Adv. Synth. Catal. 2013, 355, 809. doi: 10.1002/adsc.201200874
[32]	Meyer, A. U.; Jäger, S.; Hari, D. P.; König, B. Adv. Synth. Catal. 2015, 357, 2050. doi: 10.1002/adsc.v357.9
[33]	Kumar, J.; Ahmad, A.; Rizvi, M. A.; Ganie, M. A.; Khajuria, C.; Shah, B. A. Org. Lett. 2020, 22, 5661. doi: 10.1021/acs.orglett.0c02055
[34]	Liang, G.; Wang, J.-H.; Lei, A.; Cheng, Y.-Y.; Zhou, C.; Chen, Y.-J.; Ye, C.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2021, 23, 8082. doi: 10.1021/acs.orglett.1c03090 pmid: 34609892
[35]	Rahaman, R.; Hoque, M. T.; Maiti, D. K. Org. Lett. 2022, 24, 6885. doi: 10.1021/acs.orglett.2c02307
[36]	Wang, P.; Zhang, H.; Nie, X.; Xu, T.; Liao, S.-H. Nat. Commun. 2022, 13, 3370. doi: 10.1038/s41467-022-31089-7
[37]	Nie, X.-L.; Xu, T.-X.; Song, J.-S.; Devaraj, A.; Zhang, B.-L.; Chen, Y.; Liao, S.-H. Angew. Chem., Int. Ed. 2021, 60, 3956. doi: 10.1002/anie.v60.8
[38]	Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696. doi: 10.1016/j.tetlet.2015.10.048
[39]	Tan, W.; Wang, C.-H.; Jiang, X.-F. Chin. J. Chem. 2019, 37, 1234. doi: 10.1002/cjoc.v37.12
[40]	Chen, Z.-R.; Jin, W.-W.; Xia, Y.; Zhang, Y.-H.; Xie, M.-W.; Ma, S.-C.; Liu, C.-J. Org. Lett. 2020, 22, 8261. doi: 10.1021/acs.orglett.0c02907
[41]	Ghosh, K. G.; Das, D.; Garai, S.; Chandu, P.; Sureshkumar, D. J. Org. Chem. 2022, 87, 8611. doi: 10.1021/acs.joc.2c00783
[42]	(a) Mulliken, R. S. J. Phys. Chem. 1952, 56, 801. pmid: 23224836
	(b) Esrafili, M. D. J. Mol. Model. 2013, 19, 1417. doi: 10.1007/s00894-012-1691-x pmid: 23224836
	(c) Mulliken, R. S. J. Am. Chem. Soc. 1950, 72, 600. doi: 10.1021/ja01157a151 pmid: 23224836
[43]	(a) Andrews, L. J. Chem. Rev. 1954, 54, 713. doi: 10.1021/cr60171a001
	(b) Foster, R. J. Phys. Chem. 1980, 84, 2135. doi: 10.1021/j100454a006
[44]	Fox, M.; Younathan, J. N.; Fryxell, G. J. Org. Chem. 1983, 15, 3109.
[45]	Sankararaman, S.; Haney, W. A.; Kochi, J. K. J. Am. Chem. Soc. 1987, 109, 7824. doi: 10.1021/ja00259a035
[46]	(a) Crisenza, G. E. M.; Mazzarella, D.; Melchiorre, P. J. Am. Chem. Soc. 2020, 142, 5461. doi: 10.1021/jacs.0c01416 pmid: 32134647
	(b) Kale, M. J.; Avanesian, T.; Christopher, P. ACS Catal. 2013, 4, 116. doi: 10.1021/cs400993w pmid: 32134647
[47]	Rosokha, S. V.; Kochi, J. K. Acc. Chem. Res. 2008, 41, 641. doi: 10.1021/ar700256a
[48]	Liu, B.; Lim, C.-H.; Miyake, G. M. J. Am. Chem. Soc. 2017, 139, 13616. doi: 10.1021/jacs.7b07390
[49]	Uchikura, T.; Hara, Y.; Tsubono, K.; Akiyama, T. ACS Org. Inorg. Au 2021, 1, 23. doi: 10.1021/acsorginorgau.1c00007
[50]	Li, Y.; Miao, T.; Li, P.; Wang, L. Org. Lett. 2018, 20, 1735. doi: 10.1021/acs.orglett.8b00171
[51]	Ho, H. E.; Pagano, A.; Rossi-Ashton, J. A.; Donald, J. R.; Epton, R. G.; Churchill, J. C.; James, M. J.; O'Brien, P.; Taylor, R. J. K.; Unsworth, W. P. Chem. Sci. 2019, 11, 1353. doi: 10.1039/C9SC05311E
[52]	Yang, M.-C.; Cao, T.-P.; Xu, T.-X.; Liao, S.-H. Org. Lett. 2019, 21, 8673. doi: 10.1021/acs.orglett.9b03284
[53]	Li, Y.; Ma, F.; Li, P.-H.; Miao, T.; Wang, L. Adv. Synth. Catal. 2019, 361, 1606. doi: 10.1002/adsc.v361.7
[54]	Cai, Y.; Nie, F.-Y.; Song, Q.-H. J. Org. Chem. 2021, 86, 12419. doi: 10.1021/acs.joc.1c01433
[55]	Sundaravelu, N.; Nandy, A.; Sekar, G. Org. Lett. 2021, 23, 3115. doi: 10.1021/acs.orglett.1c00806 pmid: 33826352
[56]	Liang, X.; Li, Y.-F.; Xia, Q.; Cheng, L.; Guo, J.-B.; Zhang, P.; Zhang, W.-H.; Wang, Q.-M. Green Chem. 2021, 23, 8865. doi: 10.1039/D1GC03239A
[57]	Chen, Z.-R.; Xue, F.; Liu, T.-X.; Wang, B.; Zhang, Y.-H.; Jin, W.-W.; Xia, Y.; Liu, C.-J. Green Chem. 2022, 24, 3250. doi: 10.1039/D2GC00121G
[58]	Chen, Z.-R.; Xue, F.; Zhang, Y.-H.; Jin, W.-W.; Wang, B.; Xia, Y.; Xie, M.-W.; Abdukader, A.; Liu, C.-J. Org. Lett. 2022, 24, 3149. doi: 10.1021/acs.orglett.2c00867
[59]	Wu, Q.; Zhao, Y.-H.; Chai, L.-L.; Li, H.-Y.; Li, H.-X. Org. Chem. Front. 2022, 9, 2977. doi: 10.1039/D2QO00155A
[60]	Xie, W.-J.; Ma, P.-J.; Zhang, Y.-J.; Xi, L.-Y.; Qiu, S.-Q.; Huang, X.; Yang, B.; Gao, Y.; Zhang, J.-M. Org. Lett. 2022, 24, 6099. doi: 10.1021/acs.orglett.2c02512
[61]	Granados, A.; Cabrera-Afonso, M. J.; Escolano, M.; Badir, S. O.; Molander, G. A. Chem. Catal. 2022, 2, 898.
[62]	Zhang, Y.; Xia, S.-D.; Shi, W.-X.; Lin, B.-Z.; Su, X.-C.; Lu, W.-W.; Wu, X.-Y.; Wang, X.; Lu, X.-J.; Yan, M.; Zhang, X.-J. Org. Lett. 2022, 24, 7961. doi: 10.1021/acs.orglett.2c03077
[63]	Cabrera-Afonso, M. J.; Granados, A.; Molander, G. A. Angew Chem., Int. Ed. 2022, 61, 1. doi: 10.1002/(ISSN)1521-3757
[64]	(a) Skourtis, S. S.; Liu, C.; Antoniou, P.; Virshup, A. M.; Beratan, D. N. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 8115. doi: 10.1073/pnas.1517189113
	(b) Scholes, G. D. Annu. Rev. Phys. Chem. 2003, 54, 57. doi: 10.1146/physchem.2003.54.issue-1
	(c) Scandola, F.; Indelli, M. T.; Chiorboli, C.; Bignozzi, C. A. Top. Curr. Chem. 1990, 158, 75.
[65]	(a) Garcia-Parajo, M. F.; Hernando, J.; Sanchez Mosteiro, G.; Hoogenboom, J. P.; van Dijk, E. M.; van Hulst, N. F. ChemPhys- Chem 2005, 6, 819.
	(b) Porter, G. B. Adv. Photochem. 1974, 9, 148.
[66]	Grosskopf, J.; Kratz, T.; Rigotti, T.; Bach, T. Chem. Rev. 2022, 122, 1626. doi: 10.1021/acs.chemrev.1c00272
[67]	Xiao, W.-J.; Zhou, Q.-Q.; Zou, Y.-Q.; Lu, L.-Q. Angew. Chem., Int. Ed. 2018, 58, 1586. doi: 10.1002/anie.v58.6
[68]	Marzo, L.; Pagire, S. K.; Reiser, O.; Konig, B. Angew. Chem., Int. Ed. 2018, 57, 10034. doi: 10.1002/anie.v57.32
[69]	Zhu, S.; Pathigoolla, A.; Lowe, G.; Walsh, D. A.; Cooper, M.; Lewis, W.; Lam, H. W. Chem.-Eur. J. 2017, 23, 17598. doi: 10.1002/chem.v23.69
[70]	Li, Y.-M.; Wang, M.; Jiang, X.-F. ACS Catal. 2017, 7, 7587. doi: 10.1021/acscatal.7b02735
[71]	Teders, M.; Henkel, C.; Anhauser, L.; Strieth-Kalthoff, F.; Gomez- Suarez, A.; Kleinmans, R.; Kahnt, A.; Rentmeister, A.; Guldi, D.; Glorius, F. Nat. Chem. 2018, 10, 981. doi: 10.1038/s41557-018-0102-z
[72]	Escobar, R. A.; Johannes, J. W. Chem.-Eur. J. 2020, 26, 5168. doi: 10.1002/chem.v26.23
[73]	Gadde, K.; Mampuys, P.; Guidetti, A.; Ching, H. Y. V.; Herrebout, W. A.; Van Doorslaer, S.; Abbaspour Tehrani, K.; Maes, B. U. W. ACS Catal. 2020, 10, 8765. doi: 10.1021/acscatal.0c02159
[74]	(a) Gravatt, C. S.; Johannes, J. W.; King, E. R.; Ghosh, A. J. Org. Chem. 2022, 87, 8921. doi: 10.1021/acs.joc.2c00631
	(b) Huang, S.; Wang, M.; Jiang, X.-F. Chem. Soc. Rev. 2022, 51, 8351. doi: 10.1039/D2CS00553K
[75]	Xu, T.-X.; Cao, T.-P.; Yang, M.-C.; Xu, R.-T.; Nie, X.-L.; Liao, S.-H. Org. Lett. 2020, 22, 3692. doi: 10.1021/acs.orglett.0c01180
[76]	(a) Li, H.-Y.; Cheng, Z.-R.; Tung, C.-H.; Xu, Z.-H. ACS Catal. 2018, 8, 8237. doi: 10.1021/acscatal.8b02194
	(b) Song, T.-T.; Li, H.-Y.; Wei, F.; Tung, C.-H.; Xu, Z.-H. Tetrahedron Lett. 2019, 60, 916. doi: 10.1016/j.tetlet.2019.02.039
[77]	Jouffroy, M.; Kelly, C. B.; Molander, G. A. Org. Lett. 2016, 18, 876. doi: 10.1021/acs.orglett.6b00208
[78]	Oderinde, M. S.; Frenette, M.; Robbins, D. W.; Aquila, B.; Johannes, J. W. J. Am. Chem. Soc. 2016, 138, 1760. doi: 10.1021/jacs.5b11244 pmid: 26840123
[79]	Santandrea, J.; Minozzi, C.; Cruche, C.; Collins, S. K. Angew. Chem., Int. Ed. 2017, 56, 12255. doi: 10.1002/anie.201705903
[80]	Zhong, S.; Zhou, Z.-W.; Zhao, F.; Mao, G.-J.; Deng, G. J.; Huang, H.-W. Org. Lett. 2022, 24, 1865. doi: 10.1021/acs.orglett.2c00478
[81]	Du, H.-W.; Liu, M.-S.; Shu, W. Org. Lett. 2022, 24, 5519. doi: 10.1021/acs.orglett.2c01915
[82]	Wei, L.-D.; Wu, C.-J.; Tung, C.-H.; Wang, W.-G.; Xu, Z.-H. Org. Chem. Front. 2019, 6, 3224. doi: 10.1039/C9QO00817A
[83]	Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Chem. Rev. 2007, 107, 2725. doi: 10.1021/cr068352x
[84]	Blanka, L.; Fagnoni, M.; Protti, S.; Rueping, M. Synthesis 2019, 51, 1243. doi: 10.1055/s-0037-1611648
[85]	Wang, H.; Wu, Q.; Zhang, J.-D.; Li, H.-Y.; Li, H.-X. Org. Lett. 2021, 23, 2078. doi: 10.1021/acs.orglett.1c00235 pmid: 33635082

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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