过渡金属催化C—S键活化与转化研究进展

doi:10.6023/cjoc202309012

摘要/Abstract

C—S键的活化, 对于药物分子、高性能聚合物和复合材料的制备以及生物医学、环境保护等领域具有重要作用, 过渡金属催化C—S键的活化与转化更是具有广泛的应用前景. 根据有机硫化物中碳原子的杂化类型进行分类, 综述了近十年来过渡金属催化C(sp)/C(sp²)/C(sp³)—S键活化与转化的研究进展, 采用不同的过渡金属催化剂, 着重讨论了底物适用性和反应机理, 并对该领域存在的挑战以及未来发展趋势进行了讨论和展望.

关键词: C—S键活化, 过渡金属催化, 有机硫化物

The activation of C—S bond plays a crucial role in the preparation of drug molecules, high-performance polymers and composite materials, as well as in biomedical, environmental protection and other fields. Transition-metal-catalyzed C—S bond activation and transformations have a wide range of application prospects. Herein, the recent advances in transition-metal-catalyzed C(sp)/C(sp²)/C(sp³)—S bond activation and transformations are summarized according to the hybridization types of carbon atoms in organosulfur compounds. Various transition metal catalysts are utilized. The substrate applicability and reaction mechanisms are emphatically discussed. Finally, the challenges and future development trends of this research field are discussed and prospected.

Key words: C—S bond activation, transition metal catalysis, organosulfur compounds

引用此文

郭凯杰, 符昕姝, 李靖, 陈艳, 胡美丽, 堵锡华, 谢屿阳, 何燕. 过渡金属催化C—S键活化与转化研究进展[J]. 有机化学, 2024, 44(4): 1124-1150.

Kaijie Guo, Xinshu Fu, Jing Li, Yan Chen, Meili Hu, Xihua Du, Yuyang Xie, Yan He. Recent Advances in Transition-Metal-Catalyzed C—S Bond Activation and Transformations[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1124-1150.

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图/表 38

图1. C—S键断裂的多种途径

Figure 1. C—S bond cleavage strategies

图2. 过渡金属催化C—S键活化反应模型

Figure 2. Modeling of transition-metal-catalyzed C—S bond activation reaction

图式1. 过渡金属铑催化炔基硫醚和末端炔烃构筑烯炔硫醚

Scheme 1. Transition metal rhodium-catalyzed alkynyl sulfides and terminal alkynes for the synthesis of alkenyl sulfides

图式2. 过渡金属钯催化β-烷硫基二烯酮衍生物构筑2-环戊烯酮的环化反应

Scheme 2. Transition metal palladium-catalyzed cyclization of β-alkylthio derivatives for the synthesis of 2-cyclopentenones

图式3. 过渡金属钯催化2-(甲硫基)苯并呋喃-3-羧酸酯和2-羟基苯基硼酸的交叉偶联和分子内酯交换过程

Scheme 3. Transition metal palladium-catalyzed the cross-coupling of (2-methylthio-3-ester)benzofurans with 2-hydroxyphenylboronic acids and sequential intramolecular transesterification process

图式4. 过渡金属钯催化苯炔与烯酮二硫代缩醛的环化反应

Scheme 4. Transition metal palladium-catalyzed cyclization of benzyne and enone dithioacetal

图式5. 过渡金属钯催化芳基硫醚与芳基锌试剂的交叉偶联反应

Scheme 5. Transition metal palladium-catalyzed the cross-coupling of aryl sulfides with arylzinc reagents

图式6. 过渡金属钯催化芳基锍盐与四芳基硼酸钠的交叉偶联反应

Scheme 6. Transition metal palladium-catalyzed the cross- coupling of arylsulfonium salt and sodium tetrarylborates

图式7. 过渡金属钯催化α-(3-丁烯酰基)烯酮二硫代缩醛的脱硫环化反应

Scheme 7. Transition metal palladium-catalyzed desulfurative carbocyclizations reaction of α-(3-butenoyl) ketene dithioacetals

图式8. α-酰基烯酮二硫代缩醛和异腈合成5-羟基-α,β-不饱和γ-内酰胺

Scheme 8. α-Acyl ketene dithioacetals and isocyanides for the synthesis of 5-hydroxy-α,β-unsaturated γ-lactams

图式9. 过渡金属钯催化芳基硼酸和Yagupolskii-Umemoto试剂的芳基化反应

Scheme 9. Transition metal palladium-catalyzed arylation of arylboronic acids with Yagupolskii-Umemoto reagents

图式10. 过渡金属钯催化末端炔烃和杂芳基硫醚的偶联反应

Scheme 10. Transition metal palladium-catalyzed carbothiolation of terminal alkynes and azolyl sulfides

图式11. 过渡金属钯催化四取代α-氧代烯酮二硫代缩醛与丙二烯酸酯的[4+1]环化反应

Scheme 11. Transition metal palladium-catalyzed the [4+1] annulation of tetrasubstituted α-oxo ketene dithioacetals and allenoates

图式12. 过渡金属钯催化叔丁基异腈插入杂芳基硫醚中C(sp2)—S键的羰基化反应

Scheme 12. Transition metal palladium-catalyzed the carbonylation of tert-butyl isocyanides into the C(sp2)—S bonds of heteroaryl sulfides

图式13. 过渡金属钯催化芳基二甲基锍的烷氧羰基化反应

Scheme 13. Transition metal palladium-catalyzed alkoxycarbonylation of aryldimethylsulfoniums

图式14. 过渡金属钯催化杂芳基硫醚和末端炔烃的偶联反应

Scheme 14. Transition metal palladium-catalyzed carbothiolation of terminal alkynes with heteroaryl sulfides

图式15. 过渡金属钯催化二乙烯基硫醚C—S键活化羰基化反应

Scheme 15. Transition metal palladium-catalyzed carbonylative C—S bond activation of divinyl sulfides

图式16. 过渡金属钯催化不饱和烯烃的分子内环化反应

Scheme 16. Tr ansition metal palladium catalyzes the intramolecular cyclization of alkenes

图式17. 过渡金属钯催化芳基硫醚的Buchwald-Hartwig胺化和C—S复分解

Scheme 17. Transition metal palladium-catalyzed Buchwald-Hartwig amination and C—S metathesis of aryl sulfides

图式18. 过渡金属镍催化格氏试剂和含硫底物的交叉偶联反应

Scheme 18. Transition metal nickel-catalyzed the cross-coupling of sulfur-functionalities and Grignard reagents

图式19. 过渡金属镍催化芳基甲基亚砜和芳基锌试剂的Negishi型交叉偶联

Scheme 19. Transition metal nickel-catalyzed Negishi-type cross-coupling of aryl methyl sulfoxides and arylzinc reagents

图式20. 过渡金属镍催化芳基二甲基锍三氟甲磺酸盐和锌粉合成无盐芳基三氟甲磺酸锌

Scheme 20. Transition metal nickel-catalyzed aryldimethylsulfonium triflates and zinc powder for the synthesis of salt-free arylzinc triflates

图式21. 过渡金属镍催化炔烃和2-(三氟甲基)-1,3-苯并噻唑合成2-(三氟甲基)喹啉

Scheme 21. Transition metal nickel-catalyzed alkyne and 2-(trifluoromethyl)-1,3-benzothiazole for the synthesis of 2-(trifluoromethyl)- quinoline

图式22. 过渡金属镍催化惰性C(sp2)—S键断裂合成含硫多环化合物

Scheme 22. Transition metal nickel-catalyzed non-activated C(sp2)—S bond cleavage for the synthesis of sulfur-containing polycyclic compounds

图式23. 过渡金属镍催化芳基碘和硫代乙酸酯的羰基化合成硫酯

Scheme 23. Transition metal nickel-catalyzed carbonylation of aryl iodides and thioacetates for the synthesis of thioesters

图式24. 过渡金属铑催化芳基甲基硫醚衍生物与芳基环硼氧烷的交叉偶联反应

Scheme 24. Transition metal rhodium-catalyzed the cross-coupling of aryl methyl thioether derivatives and aryl boroxines

图式25. 过渡金属铑催化烷基芳基硫醚中C(sp2)—S键断裂的异硼基化反应

Scheme 25. Transition metal rhodium-catalyzed ipso-borylation of alkyl aryl sulfides via C(sp2)—S bond cleavage

图式26. 过渡金属铁催化α-氧代烯酮二硫代缩醛和β-酮酯及其类似物合成多取代呋喃衍生物

Scheme 26. Transition metal iron-catalyzed α-oxo ketene dithioacetals with β-ketoesters and analogues for the synthesis of tetrasubstituted furans

图式27. 过渡金属铁催化硫醚合成芳基硅烷

Scheme 27. Transition metal iron-catalyzed sulfides for the synthesis of arylsilanes

图式28. 过渡金属铜、L-脯氨酸催化2-(2-溴苯基)-4,5-二芳基-1H-咪唑和乙基黄原酸钾合成双(2-(4,5-二芳基-1H-咪唑2-基)苯基)硫烷衍生物

Scheme 28. Transition metal copper/L-proline-catalyzed 2-(2-bromophenyl)-4,5-diaryl-1H-imidazole with potassium ethylxanthate for the synthesis of bis(2-(4,5-diaryl-1H-imidazol-2-yl)phenyl)sulfane derivatives

图式29. 过渡金属钯、铜催化末端炔烃和芳基硫鎓盐的Sonogashira交叉偶联反应

Scheme 29. Transition metal palladium/copper-catalyzed Sonogashira cross-coupling of terminal alkynes with arylsulfonium salts

图式30. 过渡金属钯催化砜类化合的连续催化芳基化反应

Scheme 30. Transition metal palladium-catalyzed sequential catalytic arylations of sulfone compounds

图式31. 过渡金属钯催化芳基酰胺衍生物与烷基二苯并噻吩盐的直接邻位烷基化反应

Scheme 31. Transition metal palladium-catalyzed direct ortho alkylation of aromatic amide derivatives and alkyl dibenzothiophenium salts

图式32. 过渡金属钯催化芳基卤化物与硫醚、硫酯的分子间转硫醚化反应

Scheme 32. Transition metal palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters

图式33. 过渡金属钯催化芳基重氮盐或芳胺与4-甲硫基-2-丁酮的直接羰基硫甲基化反应

Scheme 33. Transition metal palladium-catalyzed direct carbonylative thiomethylation of aryldiazonium salts or aromatic amines with 4-methylthio-2-butanone

图式34. 过渡金属铁催化链状α-氧代烯酮二硫代缩醛与醇的串联Friedel-Crafts烷基化水解反应

Scheme 34. Transition metal iron-catalyzed tandem Friedel-Crafts alkylation-hydrolysis reaction of chain α-oxo ketene dithioacetals with alcohols

图式35. 过渡金属铑催化苄基硫醚和芳基羧酸的交叉偶联反应

Scheme 35. Transition metal rhodium-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids

图式36. 过渡金属钯、铜催化末端炔烃和(2-溴乙基)二苯基锍三氟甲磺酸盐的Sonogashira交叉偶联反应

Scheme 36. Transition metal palladium/copper-catalyzed Sono- gashira cross-coupling of terminal alkynes with (2-bromoethyl)- diphenylsulfonium triflate

参考文献 53

[1]	(a) Wächtershäuser G. Trans. R. Soc. B 2006, 361, 1787. doi: 10.1098/rstb.2006.1904 pmid: 20704269
	(b) Harpp D. N.; Vines S. M.; Montillier J. P.; Chan T. H. J. Org. Chem. 1976, 41, 3987. doi: 10.1021/jo00887a012 pmid: 20704269
	(c) Grochowski M. R.; Li T.; Brennessel W. W.; Jones W. D. J. Am. Chem. Soc. 2010, 132, 12412. doi: 10.1021/ja104158h pmid: 20704269
[2]	(a) Boyd D. A. Angew. Chem., Int. Ed. 2016, 55, 15486. doi: 10.1002/anie.v55.50
	(b) Liu J.; Yang J.; Yang Q.; Wang G.; Li Y. Adv. Funct. Mater. 2005, 15, 1297. doi: 10.1002/(ISSN)1616-3028
	(c) Dondoni A. Angew. Chem., Int. Ed. 2008, 120, 9133. doi: 10.1002/ange.v120:47
[3]	(a) Natarajan A.; Guo Y.; Harbinski F.; Fan Y.-H.; Chen H.; Luus L.; Diercks J.; Aktas H.; Chorev M.; Halperin J. A. J. Med. Chem. 2004, 47, 4979. pmid: 19588965
	(b) Cole D. C.; Lennox W. J.; Lombardi S.; Ellingboe J. W.; Bernotas R. C.; Tawa G. J.; Mazandarani H.; Smith D. L.; Zhang G.; Coupet J.; Schechter L. E. J. Med. Chem. 2005, 48, 353. doi: 10.1021/jm049243i pmid: 19588965
	(c) Banerjee M.; Poddar A.; Mitra G.; Surolia A.; Owa T.; Bhattacharyya B. J. Med. Chem. 2005, 48, 547. pmid: 19588965
	(d) Feng E.; Huang H.; Zhou Y.; Ye D.; Jiang H.; Liu H. J. Comb. Chem. 2010, 12, 422. doi: 10.1021/cc9001839 pmid: 19588965
	(e) Gao G.-Y.; Colvin A. J.; Chen Y.; Zhang X. P. J. Org. Chem. 2004, 69, 8886. doi: 10.1021/jo048552d pmid: 19588965
	(f) Inamoto K.; Hasegawa C.; Hiroya K.; Doi T. Org. Lett. 2008, 10, 5147. doi: 10.1021/ol802033p pmid: 19588965
	(g) Jegelka M.; Plietker B. Org. Lett. 2009, 11, 3462. doi: 10.1021/ol901297s pmid: 19588965
	(h) Niu P.; Kang J.; Tian X.; Song L.; Liu H.; Wu J.; Yu W.; Chang J. J. Org. Chem. 2015, 80, 1018. doi: 10.1021/jo502518c pmid: 19588965
[4]	(a) Fang R.; Xu J.; Wang D.-W. Energy Environ. Sci. 2020, 13, 432. doi: 10.1039/C9EE03408K
	(b) Shi F.; Yu J.; Chen C.; Lau S. P.; Lv W.; Xu Z.-L. J. Mater. Chem. A 2022, 10, 19412. doi: 10.1039/D2TA02217F
	(c) Li M.; Chen H.; Wang Y.; Chen X.; Wu J.; Su J.; Wang M.; Li X.; Li C.; Ma L.; Li X.; Chen Y. J. Mater. Chem. A 2023, 11, 11721. doi: 10.1039/D3TA01803B
[5]	(a) Luque R. Curr. Org. Synth. 2011, 8, 1. doi: 10.2174/157017911794407665
	(b) Ornellas S. D.; Storr T. E.; Williams T. J.; Baumann C. G.; Fairlamb I. J. S. Curr. Org. Synth. 2011, 8, 79. doi: 10.2174/157017911794407656
	(c) Wang L.; He W.; Yu Z. Chem. Soc. Rev. 2013, 42, 599. doi: 10.1039/C2CS35323G
	(d) Modha S. G.; Mehta V. P.; Eycken E. V. Chem. Soc. Rev. 2013, 42, 5042. doi: 10.1039/c3cs60041f
	(e) Lou J.; Wang Q.; Wu P.; Wang H.; Zhou Y. G.; Yu Z. Chem. Soc. Rev. 2020, 49, 4307. doi: 10.1039/C9CS00837C
	(f) Huang S.; Wang M.; Jiang X. Chem. Soc. Rev. 2022, 51, 8351. doi: 10.1039/D2CS00553K
	(g) Otsuka S.; Nogi K.; Yorimitsu H. Top. Curr. Chem. 2018, 376, 13.
[6]	(a) Li Y.; Wang H.; Wang Z.; Alhumade H.; Huang Z.; Lei A. Chem. Sci. 2023, 14, 372. doi: 10.1039/D2SC05507D
	(b) Tyagi A.; Taneja N.; Khan J.; Hazra C. K. Adv. Synth. Catal. 2023, 365, 1247. doi: 10.1002/adsc.v365.8
	(c) Liang D.; Wang M.; Bekturhun B.; Xiong B.; Liu Q. Adv. Synth. Catal. 2010, 352, 1593. doi: 10.1002/adsc.v352:10
	(d) Liu Y.; Wang M.; Yuan H.; Liu Q. Adv. Synth. Catal. 2010, 352, 884. doi: 10.1002/adsc.v352:5
	(e) Liu Y.; Liu J.; Wang M.; Liu J.; Liu Q. Adv. Synth. Catal. 2012, 354, 2678. doi: 10.1002/adsc.v354.14/15
	(f) Yu H.; Yu Z. Angew. Chem. 2009, 121, 2973. doi: 10.1002/ange.v121:16
	(g) Dong Y.; Wang M.; Liu J.; Ma W.; Liu Q. Chem. Commun. 2011, 47, 7380. doi: 10.1039/c1cc11382h
	(h) Verma R. K.; Verma G. K.; Shukla G.; Singh M. S. RSC Adv. 2012, 2, 2413. doi: 10.1039/c2ra00987k
	(i) Jin W.; Du W.; Yang Q.; Yu H.; Chen J.; Yu Z. Org. Lett. 2011, 13, 4272. doi: 10.1021/ol201620g
[7]	Yang K.; Li Q.; Li Z.; Sun X. Chem. Commun. 2023, 59, 5343. doi: 10.1039/D3CC00377A
[8]	Liebeskind L. S.; Srogl J.; Savarin C.; Polanco C. Pure Appl. Chem. 2002, 74, 115. doi: 10.1351/pac200274010115
[9]	Iwasaki M.; Fujino D.; Wada T.; Kondoh A.; Yorimitsu H.; Oshima K. Chem. Asian J. 2011, 6, 3190. doi: 10.1002/asia.v6.12
[10]	Arisawa M.; Igarashi Y.; Tagami Y.; Yamaguchi M.; Kabuto C. Tetrahedron Lett. 2011, 52, 920 doi: 10.1016/j.tetlet.2010.12.065
[11]	Shibata T.; Mitake A.; Akiyamac Y.; Stephen K. K. Chem. Commun. 2017, 53, 9016. doi: 10.1039/C7CC04997H
[12]	Beletskaya I. P.; Ananikov V. P. Chem. Rev. 2022, 122, 16110. doi: 10.1021/acs.chemrev.1c00836 pmid: 36112510
[13]	(a) Beletskaya I. P.; Alonso F.; Tyurin V. Coord Chem. Rev. 2019, 385, 137. doi: 10.1016/j.ccr.2019.01.012
	(b) Buchspies J.; Szostak M. Catalysts 2019, 9, 53. doi: 10.3390/catal9010053
	(c) Das P.; Linert W. Coord. Chem. Rev. 2016, 311, 1. doi: 10.1016/j.ccr.2015.11.010
	(d) Han F.-S. Chem. Soc. Rev. 2013, 42, 5270. doi: 10.1039/c3cs35521g
	(e) Hooshmand S. E.; Heidari B.; Sedghi R.; Varma R. S. Green chem. 2019, 21, 381. doi: 10.1039/c8gc02860e
	(f) Lennox A. J. J.; Lloyd-Jones G. C. Chem. Soc. Rev. 2014, 43, 412. doi: 10.1039/C3CS60197H
	(g) Lamblin M.; Nassar-Hardy L.; Hierso J.-C.; Fouquet E.; Felpin F.-X. Adv. Synth. Catal. 2010, 352, 33. doi: 10.1002/adsc.v352:1
[14]	Liu B.; Zheng G.; Liu X.; Xu C.; Liu J.; Wang M. Chem. Commun. 2013, 49, 2201. doi: 10.1039/c3cc37571d
[15]	Liu J.; Liu Y.; Du W.; Dong Y.; Liu J.; Wang M. J. Org. Chem. 2013, 78, 7293. doi: 10.1021/jo400984h
[16]	Dong Y.; Liu B.; Chen P.; Liu Q.; Wang M. Angew. Chem. 2014, 126, 3510. doi: 10.1002/ange.v126.13
[17]	Otsuka S.; Fujino D.; Murakami K.; Yorimitsu H.; Osuka A. Chem. Eur. J. 2014, 20, 13146. doi: 10.1002/chem.v20.41
[18]	Vasu D.; Yorimitsu H.; Osuka A. Synthesis 2015, 47, 3286. doi: 10.1055/s-00000084
[19]	Liu B.; Chang J.; Zheng G.; Song X.; Wang M. Eur. J. Org. Chem. 2015, 4611.
[20]	Chang J.; Liu B.; Yang Y.; Wang M. Org. Lett. 2016, 18, 3984. doi: 10.1021/acs.orglett.6b01780 pmid: 27498923
[21]	Wang S.-M.; Wang X.-Y.; Qin H.-L.; Zhang C.-P. Chem. Eur. J. 2016, 22, 6542. doi: 10.1002/chem.v22.19
[22]	Iwasaki M.; Topolovčan N.; Hu H.; Nishimura Y.; Gagnot G.; Na nakorn R.; Yuvacharaskul R.; Nakajima K.; Nishihara Y. Org. Lett. 2016, 18, 1642. doi: 10.1021/acs.orglett.6b00503
[23]	Wang Q.; Liu Z.; Lou J.; Yu Z. Org. Lett. 2018, 20, 6007. doi: 10.1021/acs.orglett.8b02253
[24]	Otsuka S.; Nogi K.; Yorimitsu H. Angew. Chem., Int. Ed. 2018, 57, 6653. doi: 10.1002/anie.v57.22
[25]	Minami H.; Nogi K.; Yorimitsu H. Org. Lett. 2019, 21, 2518. doi: 10.1021/acs.orglett.9b00067
[26]	Uno D.; Nogi K.; Yorimitsu H. Org. Lett. 2019, 21, 8295. doi: 10.1021/acs.orglett.9b03056
[27]	Xu J.-X.; Zhao F.; Wu X.-F. Org. Biomol. Chem. 2020, 18, 9796. doi: 10.1039/D0OB02043E
[28]	Delcaillau T.; Schmitt H. L.; Boehm P.; Falk E.; Morandi B. ACS Catal. 2022, 12, 6081. doi: 10.1021/acscatal.2c01178
[29]	Yang S.; Yu X.; Poater A.; Cavallo L.; Cazin C. S. J.; Nolan S. P.; Szostak M. Org. Lett. 2022, 24, 9210. doi: 10.1021/acs.orglett.2c03717
[30]	Mond J.; Langer C.; Quincke F. J. Chem. Soc., Trans. 1890, 57, 749. doi: 10.1039/CT8905700749
[31]	Wilke G. Angew. Chem., Int. Ed. 1988, 27, 185.
[32]	Stephan Enthaler, C. I. S. M. W. Catal. Lett. 2013, 143, 424. doi: 10.1007/s10562-013-0979-5
[33]	Yamamoto K.; Otsuka S.; Nogi K.; Yorimitsu H. ACS Catal. 2017, 7, 7623. doi: 10.1021/acscatal.7b02347
[34]	Yamada K.; Yanagi T.; Yorimitsu H. Org. Lett. 2020, 22, 9712. doi: 10.1021/acs.orglett.0c03782 pmid: 33300805
[35]	Inami T.; Kurahashi T.; Matsubara S. Synlett 2021, 32, 1948. doi: 10.1055/s-0037-1610785
[36]	Shibata T.; Sekine A.; Akino M.; Ito M. Chem. Commun., 2021, 57, 9048. doi: 10.1039/D1CC03226G
[37]	Mai W.-P.; Sui H.-D.; Lv M.-X.; Lu K. J. Chem. Res. 2021, 45, 890. doi: 10.1177/17475198211028114
[38]	Pan F.; Wang H.; Shen P.-X.; Zhao J.; Shi Z.-J. Chem. Sci. 2013, 4, 1573. doi: 10.1039/c3sc22242j
[39]	Uetake Y.; Niwa T.; Hosoya T. Org. Lett. 2016, 18, 2758. doi: 10.1021/acs.orglett.6b01250 pmid: 27210907
[40]	(a) Sherry B. D.; Fürstner A. Acc. Chem. Res. 2008, 41, 1500. doi: 10.1021/ar800039x
	(b) Czaplik W. M.; Mayer M.; Cvengros, Wangelin, J.; A. Jacobi von. ChemSusChem 2009, 2, 396. doi: 10.1002/cssc.v2:5
	(c) Piontek A.; Bisz E.; Szostak M. Angew. Chem., Int. Ed. 2018, 57, 11116. doi: 10.1002/anie.v57.35
[41]	Blanksby S. J.; Ellison G. B. Acc. Chem. Res. 2003, 36, 255. doi: 10.1021/ar020230d
[42]	Lou J.; Wang Q.; Wu K.; Wu P.; Yu Z. Org. Lett. 2017, 19, 3287. doi: 10.1021/acs.orglett.7b01431
[43]	Chen S.; Guo X.; Hou H.; Geng S.; Liu Z.; He Y.; Xue X.-S.; Feng Z. Angew. Chem., Int. Ed. 2023, 62, e202303470. doi: 10.1002/anie.v62.25
[44]	Zhang Y.; Li T.-J.; Lv L.; Liu J.-Q.; Wang X.-S. J. Heterocyclic. Chem. 2022, 59, 67. doi: 10.1002/jhet.v59.1
[45]	Tian Z.-Y.; Wang S.-M.; Jia S.-J.; Song H.-X.; Zhang C.-P. Org. Lett. 2017, 19, 5454. doi: 10.1021/acs.orglett.7b02764
[46]	Li Y.; Wang H.; Wang Z.; Alhumade H.; Huang Z.; Lei A. Chem. Sci. 2023, 14, 372. doi: 10.1039/D2SC05507D
[47]	Nambo M.; Crudden C. M. Angew. Chem., Int. Ed. 2014, 53, 742. doi: 10.1002/anie.v53.3
[48]	Simkó D. C.; Elekes P.; Pázmándi V.; Novák Z. Org. Lett. 2018, 20, 676. doi: 10.1021/acs.orglett.7b03813
[49]	Li Y.; Bao G.; Wu X.-F. Chem. Sci. 2020, 11, 2187. doi: 10.1039/C9SC05532K
[50]	Tian Q.; Xu S.; Zhang C.; Liu X.; Wu X.; Li Y. J.Org. Chem. 2021, 86, 8797. doi: 10.1021/acs.joc.1c00665
[51]	Yu H.; Zhao L.; Diao Q.; Li T.; Liao P.; Hou D.; Xin G. Synlett 2017, 28, 1828. doi: 10.1055/s-0036-1588982
[52]	Zhang X.-S.; Zhang Y.-F.; Li Z.-W.; Luo F.-X.; Shi Z.-J. Angew. Chem., Int. Ed. 2015, 54, 5478. doi: 10.1002/anie.v54.18
[53]	Ming X.-X.; Wu S.; Tian Z.-Y.; Song J.-W.; Zhang C.-P. Org. Lett. 2021, 23, 6795. doi: 10.1021/acs.orglett.1c02379