碳-碳不饱和键的催化不对称氢-膦(磷)官能化反应研究进展

doi:10.6023/cjoc202405046

摘要/Abstract

手性含膦(磷)化合物广泛应用于医药、农业、材料以及不对称催化合成等领域, 因此, 发展高效方法用于合成结构多样的手性含膦(磷)化合物引起许多化学工作者的关注. 在已发展的众多合成策略中, 碳-碳不饱和键的催化不对称氢-膦(磷)官能化反应是一类高效且原子经济的方法. 利用该方法可以高效地合成多种类型的手性含膦(磷)化合物, 包括含有碳手性、轴手性、磷手性以及同时含有碳手性和磷手性中心的含膦(磷)化合物. 主要介绍了近十年碳-碳不饱和键的催化不对称氢-膦(磷)官能化反应的研究进展, 从反应机理、合成应用、存在的挑战以及未来的发展等方面进行了阐释与讨论.

关键词: 不对称催化, 碳-碳不饱和键, 氢-膦(磷)官能化, 手性含膦(磷)化合物, 膦(磷)试剂

Phosphine/Phosphorus-containing chiral compounds have a wide range of applications in pharmaceuticals industry, agriculture, functionalized materials, and asymmetric catalysis. Accordingly, the development of efficient methods for the synthesis of structurally diverse phosphine/phosphorus-containing chiral compounds has attracted the attention of chemists. Among the multitude of synthetic strategies developed, catalytic asymmetric hydrogen-phosphine/phosphorus functiona- lization of unsaturated carbon-carbon bonds stands out as a particularly efficient and atom economical method. Utilizing this strategy, a wide array of phosphine/phosphorus-containing chiral compounds can be synthesized with remarkable efficiency. The state-of-the-art studies on catalytic asymmetric hydrogen-phosphine/phosphorus functionalization of unsaturated carbon- carbon bonds in past decade are summarized. Mechanistic insights, synthetic applications, as well as challenges and opportunities of this field are elucidated and discussed.

Key words: asymmetric catalysis, unsaturated carbon-carbon bond, hydrogen-phosphine/phosphorus functionalization, chiral phosphine/phosphorus-containing compound, phosphine/phosphorus reagent

引用此文

孙婷珈, 孙国银, 孙威, 彭雪松, 廖娟, 游勇, 袁伟成. 碳-碳不饱和键的催化不对称氢-膦(磷)官能化反应研究进展[J]. 有机化学, 2024, 44(12): 3647-3677.

Tingjia Sun, Guoyin Sun, Wei Sun, Xuesong Peng, Juan Liao, Yong You, Weicheng Yuan. Advances in Catalytic Asymmetric Hydrogen-Phosphine/Phosphorus Functionalization of Unsaturated Carbon-Carbon Bonds[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3647-3677.

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图/表 51

图1. 含膦(磷)的生物活性分子及手性配体

Figure 1. Selected phosphine/phosphorus-containing bioactive molecules and chiral ligands

图式1. 碳-碳不饱和键的催化不对称氢-膦(磷)官能化反应用于构建手性含膦(磷)化合物

Scheme 1. Catalytic asymmetric hydrogen-phosphine/phosphorus functionalization for the synthesis of chiral phosphine/phosphorus- containing compounds

图式2. 催化不对称氢膦化反应的开创性工作

Scheme 2. Pioneering works of catalytic asymmetric hydrophosphination reaction

图式3. 用于催化不对称氢-膦(磷)官能化反应的各种膦(磷)试剂

Scheme 3. Various phosphine/phosphorus reagents for catalytic asymmetric hydrogen-phosphine/phosphorus functionalization

图式4. 镍催化α,β-不饱和酮与伯膦烷的不对称氢膦化

Scheme 4. Ni-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones and primary phosphines

图式5. 钳形钯络合物催化α,β-不饱和酮与仲膦烷的不对称氢膦化

Scheme 5. Pincer-Pd-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones and secondary phosphines

图式6. NHC-铜催化二芳基膦与α,β-不饱和酮的不对称氢膦化

Scheme 6. NHC-copper-catalyzed asymmetric hydrophosphination of diarylphosphines and α,β-unsaturated ketones

图式7. 钯催化二芳基膦与α,β-不饱和酰胺的不对称氢膦化

Scheme 7. Pd-catalyzed asymmetric hydrophosphination of diarylphosphines and α,β-unsaturated amides

图式8. 钯催化二芳基膦与β,γ-不饱和的α-酮类化合物的不对称氢膦化

Scheme 8. Pd-catalyzed asymmetric hydrophosphination of diarylphosphines and β,γ-unsaturated α-ketoesters

图式9. 铜(I)催化α,β-不饱和磷硫化合物的不对称氢膦化

Scheme 9. Copper-catalyzed asymmetric 1,4-hydrophosphination of α,β-unsaturated phosphine sulfides

图式10. 手性1,2-双膦类化合物的合成及其在铑催化不对称氢化反应中的应用

Scheme 10. Synthesis of chiral 1,2-bisphosphines and their application in Rh-catalyzed asymmetric hydrogenation

图式11. 铜催化α,β-不饱和酰胺的不对称氢膦化

Scheme 11. Copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated amides

图式12. 铜催化α,β-不饱和酰胺的不对称氢膦化反应机理

Scheme 12. Proposed mechanism of copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated amides

图式13. 锰催化α,β-不饱和化合物的不对称氢膦化

Scheme 13. Manganese-catalyzed asymmetric hydrophosphination of α,β-unsaturated compounds

图式14. 锰催化α,β-不饱和化合物的不对称氢膦化反应机理

Scheme 14. Proposed mechanism of manganese-catalyzed asymmetric hydrophosphination of α,β-unsaturated compounds

图式15. 镍催化α,β-不饱和酮与二芳基膦氢的不对称氢膦化

Scheme 15. Nickel-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones and diarylphosphines

图式16. 钯催化偕二氟联烯与二芳基膦氢的不对称氢膦化

Scheme 16. Pd-catalyzed asymmetric hydrophosphination of gem-difluoroallenes and diarylphosphines

图式17. 铜催化烯基异喹啉的不对称氢膦化

Scheme 17. Copper-catalyzed asymmetric hydrophosphination of alkenyl isoquinolines

图式18. 锰络合物催化末端烯基氮杂芳烃的不对称氢膦化

Scheme 18. Manganese-catalyzed asymmetric hydrophosphination of terminal alkenyl aza-heteroarenes

图式19. 钯催化二芳基膦氢与α,β,γ,δ-不饱和化合物的催化不对称1,6-氢膦化

Scheme 19. Palladium-catalyzed asymmetric 1,6-hydrophosphination of diarylphosphines and α,β,γ,δ-unsaturated compounds

图式20. 钯催化醌类化合物与二芳基膦氢的不对称1,6-氢膦化

Scheme 20. Pd-catalyzed asymmetric 1,6-hydrophosphination of benzoquinones and diarylphosphines

图式21. 钯催化非手性杂双环烯烃与二芳基膦氢的不对称氢膦化

Scheme 21. Pd-catalyzed asymmetric hydrophosphination of achiral heterobicyclic alkenes and diarylphosphines

图式22. 钯催化环丙烯类化合物与二芳基膦烷的不对称氢膦化

Scheme 22. Pd-catalyzed asymmetric hydrophosphination of cyclopropenes and diarylphosphines

图式23. 镧金属催化环丙烯类化合物与二芳基膦烷的不对称氢膦化

Scheme 23. La-catalyzed asymmetric hydrophosphinylation of cyclopropenes and diarylphosphines

图式24. 铜催化环丙烯类化合物与二芳基膦烷的不对称氢膦化

Scheme 24. Cu-catalyzed asymmetric hydrophosphination of cyclopropenes and diarylphosphines

图式25. 手性膦-烯配体的合成及其在过渡金属催化中的应用

Scheme 25. Synthesis of chiral phosphine-olefin ligands and their application in transition metal-catalysis

图式26. 钯催化内炔与仲膦烷的不对称氢膦化

Scheme 26. Pd-catalyzed asymmetric hydrophosphination of internal alkynes and secondary phosphines

图式27. 钴催化丙烯酸乙酯与磷氧化合物的不对称氢-磷官能化

Scheme 27. Cobalt-catalyzed asymmetric hydrophosphinylation of ethyl acrylate and phosphine oxides

图式28. 钴催化含咪唑导向基团的α,β-不饱和酰胺与磷氧化合物的不对称氢-磷官能化

Scheme 28. Cobalt-catalyzed asymmetric hydrophosphinylation of imidazolyl-directed α,β-unsaturated amides and phosphine oxides

图式29. 钯和镍催化1,3-二烯与磷氧化合物的不对称氢磷官能化

Scheme 29. Pd- and Ni-catalyzed asymmetric hydrophosphinylation of 1,3-dienes and phosphine oxides

图式30. 钯催化联烯与磷氧化合物的不对称氢-磷官能化

Scheme 30. Pd-catalyzed asymmetric hydrophosphinylation of allenes and phosphine oxides

图式31. 钯催化亚甲基环丙烷类化合物与磷氧化合物的不对称氢-磷官能化

Scheme 31. Pd-catalyzed asymmetric hydrophosphinylation of methylenecyclopropanes and phosphine oxides

图式32. 镍催化2-氮杂二烯与磷氧化合物的不对称氢-磷官能化

Scheme 32. Ni-catalyzed asymmetric hydrophosphinylation of 2-azadienes and phosphine oxides

图式33. 钯催化炔烃与磷氧化合物的不对称氢-磷官能化

Scheme 33. Pd-catalyzed asymmetric hydrophosphinylation of alkynes and phosphine oxides

图式34. 新型含膦手性环状单膦配体的合成

Scheme 34. Synthesis of novel P-chiral monophosphorus ligands

图式35. 钯催化炔烃与磷氧化合物的不对称氢?磷官能化

Scheme 35. Pd-catalyzed asymmetric hydrophosphorylation of alkynes and phosphine oxides

图式36. 镍催化非活化炔烃与磷氧化合物的不对称氢?磷官能化

Scheme 36. Ni-catalyzed asymmetric hydrophosphinylation of unactivated alkynes and phosphine oxides

图式37. 镍催化共轭烯炔与磷氧化合物的不对称氢?磷官能化

Scheme 37. Ni-catalyzed asymmetric hydrophosphinylation of conjugated enynes and phosphine oxides

图式38. 铜盐与手性磷酸共催化炔烃与磷氧化合物的不对称氢?磷官能化

Scheme 38. Cu/CPA-catalyzed asymmetric hydrophosphinylation of alkynes and phosphine oxides

图式39. 铜催化磷硫化合物与α,β-不饱和硫代酰胺不对称氢-磷官能化

Scheme 39. Copper-catalyzed asymmetric hydrophosphinylation of α,β-unsaturated thioamides and phosphinothioates

图式40. 手性氮杂环卡宾催化二芳基膦烷与α-溴代肉桂醛的不对称氢膦化

Scheme 40. NHC-catalyzed asymmetric hydrophosphination of diarylphosphines and α-bromoenals

图式41. 手性双功能方酰胺催化邻亚甲基醌类化合物与磷氧化合物的不对称氢?磷官能化

Scheme 41. Chiral bifunctional squaramide catalyzed asymmetric hydrophosphinylation of o-QMs methides and phosphine oxides

图式42. 手性双功能季磷盐催化对亚甲基醌类化合物与磷氧化合物的不对称氢?磷官能化

Scheme 42. Chiral bifunctional phosphonium salt catalyzed asymmetric hydrophosphinylation of p-QMs methides and phosphine oxides

图式43. 手性双功能硫脲催化对甲苯磺酰基取代的吲哚类化合物的不对称氢?磷官能化

Scheme 43. Chiral bifunctional thiourea catalyzed enantioselective hydrophosphinylation of sulfonyl indoles

图式44. 金鸡纳碱衍生的手性双功能催化剂催化磷氧化物与查尔酮类化合物的不对称氢-磷官能化

Scheme 44. Chiral bifunctional diaminomethylenemalononitrile catalyzed asymmetric hydrophosphonylation of phosphine oxides and chalcones

图式45. 手性噁唑硼烷类催化剂催化α,β-不饱和羰基化合物和磷氧化合物的不对称氢?磷官能化

Scheme 45. Chiral oxazaborolidines-catalyzed asymmetric hydrophosphinylation of α,β-unsaturated carbonyl compounds and phosphine oxides

图式46. 手性噁唑硼烷催化α,β-不饱和羰基化合物的不对称氢?磷官能化反应机理

Scheme 46. Proposed mechanism of chiral oxazaborolidines- catalyzed asymmetric hydrophosphinylation of α,β-unsaturated ketones

图式47. 手性布朗斯特碱催化1-烯基磷氧化物与磷氧化合物的不对称氢?磷官能化

Scheme 47. Chiral Br?nsted base-catalyzed asymmetric hydrophosphinylation of 1-alkenylphosphine and phosphine oxides

图式48. 手性双(胍)亚胺基磷催化1,1-乙烯基杂环氮氧化物与磷氧化合物的不对称氢?磷官能化

Scheme 48. Chiral bis(guanidino)iminophosphorane catalyzed asymmetric hydrophosphinylation of 1,1-vinylazaheterocycle N-oxides and phosphine oxides

图式49. 手性Br?nsted酸催化2-乙烯基氮杂芳烃与磷氧化合物的不对称氢?磷官能化

Scheme 49. Chiral Br?nsted acid-catalyzed asymmetric hydrophosphinylation of 2-vinylazaarenes and phosphine oxides

图式50. 有机催化剂催化硝基烯与磷硫化合物的不对称氢?磷官能化

Scheme 50. Organocatalytic asymmetric hydrophosphinylation of nitroalkenes and phosphine sulfides

参考文献 59

[1]	(a) Hecker S.-J.; Erion M.-D. J. Med. Chem. 2008, 51, 2328. doi: 10.1021/jm701260b pmid: 2066973
	(b) Sheng X.-C.; Pyun H.-J.; Chaudhary K.; Wang J.; Doerffler E.; Fleury M.; Kim C.-U. Bioorg. Med. Chem. Lett. 2009, 19, 3453. pmid: 2066973
	(c) Zhang Y.-P.; You Y.; Yin J.-Q.; Wang Z.-H.; Zhao J.-Q.; Li Q.; Yuan W.-C. Eur. J. Org. Chem. 2023, 26, e202300728. pmid: 2066973
	(d) Wiemer A.-J. ACS Pharmacol. Transl. Sci. 2020, 3, 613. pmid: 2066973
	(e) Jia X.; Schols D.; Meier C. J. Med. Chem. 2020, 63, 6003. pmid: 2066973
	(f) Atherton F. R.; Hassall C. H.; Lambert R. W. J. Med. Chem. 1986, 29, 29. pmid: 2066973
	(g) Lavielle G.; Hautefaye P.; Schaeffer C.; Boutin J. A.; Cudennec C. A.; Pierre A. J. Med. Chem. 1991, 34, 1998. pmid: 2066973
[2]	(a) Xu G.-Q.; Senanayake C.-H.; Tang W.-J. Acc. Chem. Res. 2019, 52, 1101.
	(b) Li W.-B.; Zhang J.-L. Chem. Soc. Rev. 2016, 45, 1657.
[3]	(a) Yao Q.-L.; Wang A.-J.; Pu J.-Z.; Tang Y.-M. Chin. J. Org. Chem. 2014, 34, 292 (in Chinese).
	(姚秋丽, 王安俊, 蒲家志, 唐瑜敏, 有机化学, 2014, 34, 292.) doi: 10.6023/cjoc201309008
	(b) Li Z.; Duan W.-L. Chin. J. Org. Chem. 2016, 36, 1805 (in Chinese).
	(李振, 段伟良, 有机化学, 2016, 36, 1805.) doi: 10.6023/cjoc201602018
	((c) Zhu R.-Y.; Liao K.; Yu J.-S.; Zhou J. Acta Chim. Sinica 2020, 78, 193 (in Chinese).
	(朱仁义, 廖奎, 余金生, 周剑, 化学学报, 2020, 78, 193.) doi: 10.6023/A20010002
	(d) Li H.; Yin L. Chin. J. Org. Chem. 2022, 42, 3183 (in Chinese).
	(李晖, 殷亮, 有机化学, 2022, 42, 3183.) doi: 10.6023/cjoc202208002
	(e) Luo C.; Yin Y.-L.; Jiang Z.-Y. Chin. J. Org. Chem. 2023, 43, 1963 (in Chinese).
	(罗诚, 尹艳丽, 江智勇, 有机化学, 2023, 43, 1963.) doi: 10.6023/cjoc202212024
	(f) Ding K.; Su B. Eur. J. Org. Chem. 2024, 27, e202301160.
[4]	(a) Feng J.-J.; Chen X.-F.; Shi M.; Duan W.-L. J. Am. Chem. Soc. 2010, 132, 5562.
	(b) Huang Y.-H.; Pullarkat S. A.; Li Y.-X.; Leung P.-H. Chem. Commun. 2010, 46, 6950.
[5]	Wang C.-Y.; Huang K.-S.; Ye J.; Duan W.-L. J. Am. Chem. Soc. 2021, 143, 5685.
[6]	Hao X.-Q.; Zhao Y.-W.; Yang J.-J.; Niu J.-L.; Gong J.-F. Song M.-P. Organometallics 2014, 33, 1801.
[7]	Li C.; Bian Q.-L.; Xu S.; Duan W.-L. Org. Chem. Front. 2014, 1, 541.
[8]	Song Y.-C.; Dai G.-F.; Xiao F.-H.; Duan W.-L. Tetrahedron Lett. 2016, 57, 2990.
[9]	Chen Y.-R.; Feng J.-J.; Duan W.-L. Tetrahedron Lett. 2014, 55, 595.
[10]	Chew R. J.; Lu Y.-P.; Jia Y.-X.; Li B.-B.; Wong E. H. Y.; Goh R.; Li Y.-X.; Huang Y.-H.; Pullarkat S. A.; Leung P.-H. Chem.- Eur. J. 2014, 20, 14514.
[11]	Chew R. J.; Sepp K.; Li B.-B.; Li Y.-X.; Zhu P.-C.; Tan N. S.; Leung P.-H. Adv. Synth. Catal. 2015, 357, 3297.
[12]	Chew R. J.; Teo K. Y.; Huang Y.-H.; Li B.-B.; Li Y.-X.; Pullarkat S. A.; Leung P.-H. Chem. Commun. 2014, 50, 8768.
[13]	Xu Y.; Yang Z.-H.; Ding B.-Q.; Liu D.-L.; Liu Y.-G.; Sugiya M.; Imamoto T.; Zhang W.-B. Tetrahedron 2015, 71, 6832.
[14]	Yue W.-J.; Xiao J.-Z.; Zhang S.; Yin L. Angew. Chem., Int. Ed. 2020, 59, 7057.
[15]	Li Y.-B.; Tian H.; Yin L. J. Am. Chem. Soc. 2020, 142, 20098.
[16]	Pérez J. M.; Postolache R.; Reis M. C.; Sinnema E. G.; Vargová D.; Vries F.; Otten E.; Ge L.; Harutyunyan S. R. J. Am. Chem. Soc. 2021, 143, 20071.
[17]	Ge L.; Harutyunyan S. R. Chem. Sci. 2022, 13, 1307.
[18]	Postolache R.; Pérez J. M.; Reis M. C.; Ge L.; Sinnema E. G.; Harutyunyan S. R. Org. Lett. 2023, 25, 1611. doi: 10.1021/acs.orglett.2c04256 pmid: 36892214
[19]	Wang C.-Y.; Yin P.; Dai Y.-H.; Ye J.; Duan W.-L. J. Organomet. Chem. 2023, 983, 122552.
[20]	Ji D.-Q.; Qi Z.-S.; Li X.-W. Org. Lett. 2023, 25, 5957.
[21]	Yang Q.-J.; Zhou J.; Wang J. Chem. Sci. 2023, 14, 4413.
[22]	Sinnema E. G.; Ramspoth T.-F.; Bouma R. H.; Ge L.; Harutyunyan S. R. Angew. Chem., Int. Ed. 2024, 63, e202316785.
[23]	Lu J.-Z.; Ye J.-X.; Duan W.-L. Chem. Commun. 2014, 50, 698.
[24]	Huang J.; Zhao M.-X.; Duan W.-L. Tetrahedron Lett. 2014, 55, 629.
[25]	Huang Y.-H.; Li Y.-X.; Leung P.-H.; Hayashi T. J. Am. Chem. Soc. 2014, 136, 4865.
[26]	Sadeer A.; Ong Y. J.; Kojima T.; Foo C. Q.; Li Y.-X.; Pullarkat S.-A.; Leung P.-H. Chem.-Asian J. 2018, 13, 2829.
[27]	Lu Z.-W.; Zhang H.-Y.; Yang Z.-P.; Ding N.; Meng L.; Wang J. ACS Catal. 2019, 9, 1457.
[28]	Zhang Y.-L.; Jiang Y.-X.; Li M.-L.; Huang Z.-X.; Wang J. Chem. Catal. 2022, 2, 3163.
[29]	Lin X.-B.; An K.; Zhuo Q.-D.; Nishiura M.-Y.; Cong X.-F.; Hou Z.-M. Angew. Chem., Int. Ed. 2023, 62, e202308488.
[30]	Zhang S.; Jiang N.; Xiao J.-Z.; Lin G.-Q.; Yin L. Angew. Chem., Int. Ed. 2023, 62, e202218798.
[31]	Zhang Y.-D.; Zhu S.-F. Acta Chim. Sinica 2023, 81, 777 (in Chinese).
	(张艳东, 朱守非, 化学学报, 2023, 81, 777.) doi: 10.6023/A23040125
[32]	Ji D.-Q.; Jing J.-R.; Wang Y.; Qi Z.-S.; Wang F.; Zhang X.-P.; Wang Y.; Li X.-W. Chem 2022, 8, 3346.
[33]	Wu Z.-H.; Cheng A.-Q.; Yuan M.; Zhao Y.-X.; Yang H.-L.; Wei L.-H.; Wang H.-Y.; Wang T.; Zhang Z.-T.; Duan W.-L. Angew. Chem., Int. Ed. 2021, 60, 27241.
[34]	Yu X.-H.; Lu L.-Q.; Zhang Z.-H.; Shi D.-Q.; Xiao W.-J. Org. Chem. Front. 2023, 10, 133.
[35]	Nie S.-Z.; Davison R.-T.; Dong V.-M. J. Am. Chem. Soc. 2018, 140, 16450.
[36]	Long J.; Li Y.-Q.; Zhao W.-N.; Yin G.-Y. Chem. Sci. 2022, 13, 1390.
[37]	(a) Li G.-L.; Huo X.-H.; Jiang X.-Y.; Zhang W.-B. Chem. Soc. Rev. 2020, 49, 2060. pmid: 33301308
	(b) Blieck R.; Taillefer M.; Monnier F. Chem. Rev. 2020, 120, 13545. doi: 10.1021/acs.chemrev.0c00803 pmid: 33301308
[38]	Yang Z.-P.; Wang J. Angew. Chem., Int. Ed. 2021, 60, 27288.
[39]	Zhou J.; Meng L.; Lin S.-J.; Cai B.-H.; Wang J. Angew. Chem., Int. Ed. 2023, 62, e202303727.
[40]	Duan S.-Z.; Pan A.-L.; Du Y.; Zhu G.-L.; Tian X.; Zhang H.-B.; Walsh P. J.; Yang X.-D. ACS Catal. 2023, 13, 10887.
[41]	Dai Q.; Liu L.; Qian Y.-Y.; Li W.-B.; Zhang J.-L. Angew. Chem., Int. Ed. 2020, 59, 20645.
[42]	Xie X.-X.; Li S.-L.; Chen Q.-Y.; Guo H.; Yang J.-F.; Zhang J.-L. Org. Chem. Front. 2022, 9, 1589.
[43]	Yang Z.-P.; Gu X.-D.; Han L.-B.; Wang J. Chem. Sci. 2020, 11, 7451.
[44]	Liu X.-T.; Han X.-Y.; Wu Y.; Sun Y.-Y.; Gao L.; Huang Z.; Zhang Q.-W. J. Am. Chem. Soc. 2021, 143, 11309.
[45]	Wang W.-H.; Wu Y.; Qi P.-J.; Zhang Q.-W. ACS Catal. 2023, 13, 6994.
[46]	Zhang Y.-Q.; Han X.-Y.; Wu Y.; Qi P.-J.; Zhang Q.; Zhang Q.-W. Chem. Sci. 2022, 13, 4095.
[47]	(a) Ananikov V. P.; Makarov A. V.; Beletskaya I. P. Chem.-Eur. J. 2011, 17, 12623.
	(b) Ananikov V. P.; Beletskaya I. P. Chem.-Asian J. 2011, 6, 1423.
	(c) Khemchyan L. L.; Ivanova J. V.; Zalesskiy S. S.; Ananikov V. P.; Beletskaya I. P.; Starikova Z. A. Adv. Synth. Catal. 2014, 356, 771.
[48]	Cai B.-H.; Cui Y.; Zhou J.; Wang Y.-B.; Yang L.-M.; Tan B.; Wang J. Angew. Chem., Int. Ed. 2023, 62, e202215820.
[49]	Li Y.-B.; Li Y.; Yin L. Chin. Chem. Lett. 2024, 35, 109294.
[50]	Maiti R.; Yan J.-L.; Yang X.; Mondal B.; Xu J.; Chai H.-F.; Jin Z.-C.; Robin Chi Y.-G. Angew. Chem., Int. Ed. 2021, 60, 26616.
[51]	Gu X.; Yuan H.; Jiang J.; Wu Y.; Bai W.-J. Org. Lett. 2018, 20, 7229.
[52]	Chen Y.; Yu Z.-Y.; Jiang Z.-Y.; Tan J.-P.; Wu J.-H.; Lan Y.; Ren X.-Y.; Wang T.-L. ACS Catal. 2021, 11, 14168.
[53]	Jia Y.-Q.; Zhao J.-Q.; Wang Z.-H.; You Y.; Zhang Y.-P.; Jin X.; Zhou M.-Q.; Ge Z.-Z.; Yuan W.-C. Chem. Commun. 2022, 58, 12062.
[54]	Arai R.; Hirashima S.-I.; Nakano T.; Kawada M.; Akutsu H.; Nakashima K.; Miura T. J. Org. Chem. 2020, 85, 3872.
[55]	(a) Shi Y.-R.; Chen L.-R.; Gao Q.; Li J.-L.; Guo Y.-F.; Fan B.-M. Org. Lett. 2023, 25, 6495.
	(b) Qian J.-Y.; Zhao H.-Y.; Gao Q.; Chen L.-R.; Shi Y.-R.; Li J.-L.; Guo Y.-F.; Fan B.-M. Org. Chem. Front. 2023, 10, 5672.
	(c) Chen L.-R.; Wang G.-Y.; Nong X.-F.; Shao W.-D.; Li J.-L.; Guo Y.-F.; Fan B.-M. Chem.-Eur. J. 2024, e202401017.
[56]	Kondoh A.; Ishikawa S.; Terada M. Org. Biomol. Chem. 2020, 18, 7814.
[57]	Das S.; Hu Q.-P.; Kondoh A.; Terada M. Angew. Chem., Int. Ed. 2021, 60, 1417.
[58]	Wang B.-H.; Liu Y.-L.; Jiang C.-Y.; Cao Z.; Cao S.-S.; Zhao X.-W.; Ban X.; Yin Y.-L.; Jiang Z.-Y. Angew. Chem., Int. Ed. 2023, 62, e202216605.
[59]	Hirashima S.-I.; Hirota E.; Matsushima Y.; Noda N.; Nishimura Y.; Narushima T.; Nakashima K.; Miura T. Chem.-Asian J. 2022, 17, e202200989.