C—H键不对称羟基化反应的研究进展

doi:10.6023/cjoc202412014

摘要/Abstract

手性醇类衍生物是存在于许多生物活性物质及天然产物中的一类重要的分子; 同时也是一类重要的有机合成中间体, 可用于合成许多重要的有机化合物. 仿生催化是继生物催化后较为新兴的催化不对称羟基化的反应方式, 这一类反应主要以新颖配体的设计及在不对称催化反应中的应用为创新点. 因此, 发展高效、绿色的方法合成手性醇类化合物具有重要的研究意义. 总结了近二十年来C—H键不对称羟基化的研究进展, 论文根据反应所使用的催化剂类型, 将不对称羟基化反应进行了分类总结, 主要分为生物催化、仿生催化两大类, 其中仿生催化区分了不同类型的手性配体.

关键词: 不对称羟基化, 对映选择性, 酶催化, 仿生催化, 手性配体

Chiral alcohol derivatives are an important class of molecules that exist in many bioactive substances and natural products, and are also an important class of organic synthetic intermediates used to synthesize many important organic compounds. Biomimetic catalysis has been emerging as a very powerful tool for catalytic asymmetric hydroxylation after biocatalysis, and this type of reaction is mainly innovative in the design of novel ligands and their application in asymmetric catalytic reactions. Therefore, it is of great significance to develop efficient, green and stereoselective methods for the synthesis of chiral alcohols. In this paper, the asymmetric hydroxylation of C—H bonds over the past two decades is summarized, and such reactions are classified and summarized according to the types of catalysts, which are mainly divided into two categories of biocatalysis and biomimetic catalysis.

Key words: asymmetric hydroxylation, enantioselectivity, enzymatic catalysis, biomimetic catalysis, chiral ligands

引用此文

武烨, 陈春霞, 彭进松. C—H键不对称羟基化反应的研究进展[J]. 有机化学, 2025, 45(8): 2726-2745.

Ye Wu, Chunxia Chen, Jinsong Peng. Research Progress of C—H Bond Asymmetric Hydroxylation[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2726-2745.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 48

图1. 含有手性醇结构单元的天然活性物质

Figure 1. Natural active substances containing chiral alcohol structural units

图式1. P450-CAM催化1R-(＋)-樟脑的羟基化反应

Scheme 1. P450-CAM-catalyzed hydroxylation of 1R-(＋)- camphor

图式2. P450-CAM 催化烷烃不对称羟基化反应的机理

Scheme 2. Mechanism of asymmetric hydroxylation of alkanes catalyzed by P450-CAM

图式3. P450催化肉豆蔻酸三个位点的羟基化反应

Scheme 3. P450-catalyzed the hydroxylation of myristate at three sites

图式4. 使用突变体催化底物19和20的不对称羟基化

Scheme 4. Asymmetric hydroxylation of substrates 19 and 20 was catalyzed by mutants

图式5. LG-23突变体催化六种类固醇的不对称羟基化反应

Scheme 5. LG-23 mutants catalyze asymmetric hydroxylation of six steroids

图式6. 大肠杆菌P450PL2-4对β-卤代芳烃的不对称羟基化反应

Scheme 6. Asymmetric hydroxylation of β-halogenated aromatics by E. coli P450PL2-4

图式7. H216O2或H218O2存在下对乙苯和1-苯基乙醇进行不对称羟基化反应的双模式机制

Scheme 7. Bimodal mechanism of asymmetric hydroxylation of ethylbenzene and 1-phenylethanol in the presence of H216O2 or H218O2

图式8. 丝状真菌酶催化内酯底物的不对称羟基化反应

Scheme 8. Symmetric hydroxylation of lactone substrates catalyzed by filamentous fungal enzymes

图式9. 非血红素加氧酶催化氨基酸的C—H键不对称羟基化反应

Scheme 9. Non-heme oxygenase-catalyzed C—H asymmetric hydroxylation of amino acids

图式10. 基于α-KG依赖性酶共识机制进行的羟基化反应机理

Scheme 10. Hydroxylation process based on the consensus mechanism of α-KG dependent enzymes

图式11. 使用β-环糊精-Mn-porphyrin催化剂对甾体底物进行区域和立体选择性羟基化反应

Scheme 11. Regionally and stereoselectively hydroxylation of steroid substrates was performed using β-cyclodextrin-Mn-porphyrin catalysts

图式12. 水溶性Mn-porphyrin催化烯烃不对称环氧化和不对称羟基化反应

Scheme 12. Asymmetric epoxidation of olefin and hydroxylation catalyzed by water-soluble Mn-porphyrin

图式13. Mn-porphyrin催化3,4-二氢喹诺酮底物不对称羟基化反应

Scheme 13. Mn-porphyrin catalyzed asymmetric hydroxylation of 3,4-dihydroquinolones

图式14. M(P3)Cl催化苄位不对称羟基化反应

Scheme 14. M(P3)Cl catalyzed asymmetric hydroxylation at benzyl site

图式15. Fe-porphyrin催化的烯丙基不对称羟基化反应

Scheme 15. Asymmetric hydroxylation of allyl catalyzed by Fe-porphyrins

图式16. Ru(P5)(CO)催化苄位不对称羟基化反应

Scheme 16. Ru(P5)(CO) catalyzed asymmetric hydroxylation at the benzylic site

图式17. Ru(P4)(CO)(EtOH)催化苄基C—H键不对称羟基化反应

Scheme 17. Ru(P4)(CO)(EtOH)-catalyzed asymmetric hydroxylation of benzyl C—H bond

图式18. Os(TMP)(CO)催化的区域选择性羟化反应

Scheme 18. Regional selective hydroxylation catalyzed by Os- (TMP)(CO)

图式19. Mn(III)-Salen络合物催化苄位C—H键不对称羟基化反应

Scheme 19. Asymmetric benzyl C—H hydroxylation catalyzed by Mn(III)-Salen complex

图式20. 凹型Mn(III)-Salen手性催化剂

Scheme 20. Chiral concave Mn(III)-Salen catalyst

图式21. Fe(III)-Salan催化β-酮酯不对称羟基化反应

Scheme 21. Fe(III)-Salan catalyzed asymmetric hydroxylation of β-ketoesters

图式22. Zr(lV)-Salan催化β-酮酯的不对称羟基化反应

Scheme 22. Zr(lV)-Salan catalyzed asymmetric hydroxylation of β-ketoesters

图式23. 改进的Zr(lV)-Salan催化β-酮酯的不对称羟基化反应

Scheme 23. Modified Zr(lV)-Salan catalyzed asymmetric hydroxylation of β-ketoesters

图式24. Zr(lV)-Salan催化β-酮酯的不对称羟基化反应的反应机理

Scheme 24. Reaction mechanism of asymmetric hydroxylation of β-keto esters catalyzed by Zr(lV)-Salan

图式25. 新型硝基取代Ti-Salalen催化苄位C—H不对称羟基化

Scheme 25. The novel nitro-substituted Ti-Salalen-catalyzes the asymmetric hydroxylation of benzyl C—H

图2. Ti-Salalen催化剂二聚体结构

Figure 2. The catalyst structure of Ti-Salalen dimer

图式26. Mn-Salen催化的炔丙位叔C(sp3)—H键的不对称羟基化

Scheme 26. Asymmetric hydroxylation of tertiary propargyl C(sp3)—H bonds catalyzed by Mn-Salen

图式27. 氨基吡啶基过渡金属催化剂

Scheme 27. Transition metal catalysts based on aminopyridines

图式28. Fe-氨基吡啶催化烷基C—H键羟基化反应

Scheme 28. Fe-aminopyridine catalyzes the hydroxylation of alkyl C—H bond

Entry	Product	Isolated yield/% (rsm^a)
1		46 (26)
2		53 (43)
3		60 (18)
4		43 (33)
5		52 (21)
6		57 (27)
7		43 (42)
8		33 (67) 90*^,^b(8)
9		52 (20)
10		92*

表1. 催化剂98对不同类型底物的适用范围

Table 1. Range of 98 for different types of substrates

图式29. EWG影响下C—H键反应活性顺序

Scheme 29. Order of C—H bond reactivity under the influence of EWG

图式30. 顺-1,2-二甲基环己烷立体特异性羟基化反应

Scheme 30. Stereospecific tertiary C—H hydroxylation of cis-1,2-dimethyl cyclohexane

图式31. 催化剂101催化烷基C—H键氧化反应

Scheme 31. 101 catalyzed aliphatic C—H oxidation

图式32. 催化剂102~104催化的C—H键氧化反应

Scheme 32. C—H bond oxidation catalyzed by 102-104

图式33. (＋)-新薄荷脑新戊酸酯136选择性氧化反应

Scheme 33. Selective oxidation of (＋)-neomenthol neopentanoate 136

图式34. 反式雄酮醋酸酯138的催化氧化

Scheme 34. Selective oxidation of (＋)-neomenthol neopentanoate 138

Entry	Cat.	Conv/%	Total yield (isolated yield)/%	C6/C7/C12/C14
1	107c	85	70 (50)	75/5/23/—
2	107d	86	80 (71)	11/1/88/—
3	108c	83	60 (49)	82/12/3/3
4	108d	50	48 (33)	22/6/69/3

表2. 反式雄酮醋酸酯的氧化

Table 2. Oxidation of trans-androsterone acetate

图式35. (a)极性反转概念示意图; (b)基于氢原子转移机制进行的C—H键羟基化反应

Scheme 35. (a) Schematic diagram of the polarity reversal concept; (b) C—H hydroxylation mechanism entailing hydrogen atom transfer

图式36. Mn催化氟化乙醇溶液中的苄位不对称羟基化反应

Scheme 36. Mn catalyzed asymmetric benzyl hydroxylation in fluorinated ethanol

图式37. 螺旋环烃的高对映选择性氧化反应

Scheme 37. Highly enantioselective oxidation of helicoidal hydrocarbons

图式38. 螺环底物中的苄位C—H不对称氧化反应

Scheme 38. Enantioselective benzyl C—H oxidation of spirocycles

图式39. Mn催化氢化茚苄位C—H不对称羟基化反应及机理

Scheme 39. Mn-catalyzed asymmetric benzyl hydroxylation of indene derivatives and mechanism

图式40. (－)-降龙涎香醚及其衍生物C—H氧化反应

Scheme 40. C—H oxidation of (－)-norambergris ether and its derivatives

图式41. 雌酮-3-醋酸酯、17α-和17β-雌二醇-3-醋酸酯底物的C—H键羟基化反应

Scheme 41. C—H hydroxylation of estrone 3-acetate, 17α- and 17β-estradiol 3-acetate substrates

图式42. 未活化亚甲基的C—H键不对称氧化

Scheme 42. Asymmetric oxidation of C—H bonds of unactivated methylene

图式43. 未活化叔C(sp3)—H键非导向对映选择性羟基化反应

Scheme 43. Nondirected enantioselective hydroxylation of the unactivated tertiary C—H bond

图式44. HFIP溶剂辅助的杂芳香底物远程C—H键羟基化反应

Scheme 44. HFIP-assisted distant C—H hydroxylation of heteroaromatic substrates

参考文献 76

[1]	(a) Han, Y.-Q.; Shi, B.-F. Acta Chim. Sinica 2023, 81, 1522 (in Chinese).
	(韩叶强, 史炳锋, 化学学报, 2023, 81, 1522.) doi: 10.6023/A23070336
	(b) Huang, J.-X.; Liu, M.; Xu, H.; Dai, H.-X. Acta Chim. Sinica 2024, 82, 565 (in Chinese).
	(黄佳鑫, 刘敏, 徐辉, 戴辉雄, 化学学报, 2024, 82, 565.) doi: 10.6023/A24040136
[2]	Shul’pin, G. B. Catalysts 2016, 6, 50.
[3]	(a) Nakayama, M.; Fukuoka, Y.; Nozaki, H.; Matsuo, A.; Hayashi, S. Chem. Lett. 2006, 9, 1243. pmid: 14978831
	(b) Christoffers, J.; Werner, T.; Frey, W.; Baro, A. Chem.-Eur. J. 2004, 10, 1042. doi: 10.1002/chem.200305486 pmid: 14978831
[4]	Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. J. Nat. Prod. 2000, 63, 79. pmid: 10650083
[5]	Zhou, Y.-H.; Li, X.-B.; Zhang, J.-Z.; Li, L.; Zhang, M.; Chang, W.-Q.; Wang, X.-N.; Lou, H.-X. J. Asian Nat. Prod. Res. 2016, 18, 409.
[6]	Davis, F. A.; Clark, C.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1994, 59, 1184.
[7]	Crout, D. H. G.; Lee, E. R.; Pearson, D. P. J. J. Chem. Soc., Chem. Commun. 1990, 331.
[8]	Yang, F. Ph.D. Dissertation, Dalian University of Techonology, Dalian, 2019 (in Chinese).
	(杨帆, 博士论文, 大连理工大学, 大连, 2019.)
[9]	Huang, Z.-X.; Lim, H. N.; Mo, F.-Y.; Young, M. C.; Dong, G.-B. Chem. Soc. Rev. 2015, 44, 7764.
[10]	Acocella, M. R.; Mancheño, O. G.; Bella, M.; Jørgensen, K. A. J. Org. Chem. 2004, 69, 8165. pmid: 15527315
[11]	Kille, S.; Zilly, F. E.; Acevedo, J. P.; Reetz, M. T. Nat. Chem. 2011, 3, 738.
[12]	Xiao, X.; Xu, K.; Gao, Z.-H.; Zhu, Z.-H.; Ye, C.; Zhao, B.; Luo, S.; Ye, S.; Zhou, Y.-G.; Xu, S.; Zhu, S.-F.; Bao, H.; Sun, W.; Wang, X.; Ding, K. Sci. China: Chem. 2023, 66, 1553.
[13]	(a) Sundén, H.; Engqvist, M.; Casas, J.; Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2004, 43, 6532.
	(b) Tang, X.-F.; Zhao, J.-N.; Wu, Y.-F.; Feng, S.-H.; Yang, F.; Yu, Z.-Y.; Meng, Q.-W. Adv. Synth. Catal. 2019, 361, 5245.
[14]	Sun, Q.-S.; Sun, W. Chin. J. Org. Chem. 2020, 40, 3686 (in Chinese).
	(孙强盛, 孙伟, 有机化学, 2020, 40, 3686.) doi: 10.6023/cjoc202006008
[15]	Talsi, E. P.; Samsonenko, D. G.; Ottenbacher, R. V.; Bryliakov, K. P. ChemCatChem 2017, 9, 4580.
[16]	Wei, Y.-F.; Ang, E. L.; Zhao, H.-M. Curr. Opin. Chem. Biol. 2018, 43, 1.
[17]	Maryniak, D. M.; Kadkhodayan, S.; Crull, G. B.; Bryson, T. A.; Dawson, J. H. Tetrahedron 1993, 49, 9373.
[18]	(a) Groves, J. T.; McClusky, G. A. J. Am. Chem. Soc. 1976, 98, 859.
	(b) Groves, J. T. J. Chem. Educ. 1985, 62, 928.
[19]	(a) Huang, X.-Y.; Groves, J. T. JBIC, J. Biol. Inorg. Chem. 2017, 22, 185.
	(b) Cho, K.-B.; Hirao, H.; Shaik, S.; Nam, W. Chem. Soc. Rev. 2016, 45, 1197.
[20]	Urlacher, V.; Schmid, R. D. Curr. Opin. Biotechnol. 2002, 13, 557.
[21]	Peters, M. W.; Meinhold, P.; Glieder, A.; Arnold, F. H. J. Am. Chem. Soc. 2003, 125, 13442.
[22]	Bell, S. G.; Spence, J. T. J.; Liu, S.; George, J. H.; Wong, L.-L. Org. Biomol. Chem. 2014, 12, 2479.
[23]	Li, A.-T.; Acevedo-Rocha, C. G.; D'Amore, L.; Chen, J.-F.; Peng, Y.-Q.; Garcia-Borràs, M.; Gao, C.-H.; Zhu, J.-M.; Rickerby, H.; Osuna, S.; Zhou, J.-H.; Reetz, M. T. Angew. Chem., Int. Ed. 2020, 59, 12499.
[24]	Cui, H.-B.; Xie, L.-Z.; Wan, N.-W.; He, Q.; Li, Z.; Chen, Y.-Z. Green Chem. 2019, 21, 4324.
[25]	Kluge, M.; Ullrich, R.; Scheibner, K.; Hofrichter, M. Green Chem. 2012, 14, 440.
[26]	Mazur, M.; Gładkowski, W.; Pawlak, A.; Obmińska-Mrukowicz, B.; Maciejewska, G.; Wawrzeńczyk, C. Molecules 2019, 24, 666.
[27]	Pavon, J. A.; Fitzpatrick, P. F. Biochemistry 2006, 45, 11030.
[28]	Kovaleva, E. G.; Lipscomb, J. D. Nat. Chem. Biol. 2008, 4, 186. doi: 10.1038/nchembio.71 pmid: 18277980
[29]	Kal, S.; Que, L. JBIC, J. Biol. Inorg. Chem. 2017, 22, 339.
[30]	Hanauske-Abel, H. M.; Günzler, V. J. Theor. Biol. 1982, 94, 421. pmid: 6281585
[31]	Lu, H.-J.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899.
[32]	Yang, J.; Gabriele, B.; Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057.
[33]	Srour, H.; Maux, P. L.; Simonneaux, G. Inorg. Chem. 2012, 51, 5850.
[34]	Halterman, R. L.; Jan, S.-T.; Nimmons, H. L.; Standlee, D. J.; Khan, M. A. Tetrahedron 1997, 53, 11257.
[35]	Burg, F.; Gicquel, M.; Breitenlechner, S.; Pöthig, A.; Bach, T. Angew. Chem., Int. Ed. 2018, 57, 2953.
[36]	Groves, J. T.; Viski, P. J. Am. Chem. Soc. 1989, 111, 8537.
[37]	John, T.; Groves.; Peter, V. J. Org. Chem. 1990, 55, 3628.
[38]	Konoike, T.; Araki, Y.; Kanda, Y. Tetrahedron Lett. 1999, 40, 6971.
[39]	Gross, Z.; Ini, S. Org. Lett. 1999, 1, 2077.
[40]	Zhang, R.; Yu, W.-Y.; Che, C.-M. Tetrahedron: Asymmetry 2005, 16, 3520.
[41]	Iida, T.; Ogawa, S.; Hosoi, K.; Makino, M.; Fujimoto, Y.; Goto, T.; Mano, N.; Goto, J.; Hofmann, A. F. J. Org. Chem. 2007, 72, 823.
[42]	Ogawa, S.; Hosoi, K.; Iida, T.; Wakatsuki, Y.; Makino, M.; Fujimoto, Y.; Hofmann, A. F. Eur. J. Org. Chem. 2007, 2007, 3555.
[43]	Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410.
[44]	Wen, Y.-Q.; Ren, W.-M.; Lu, X.-B. Chin. Chem. Lett. 2011, 22, 1285.
[45]	Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979.
[46]	Hamada, T.; Irie, R.; Mihara, J.; Hamachi, K.; Katsuki, T. Tetrahedron 1998, 54, 10017.
[47]	Gu, X.; Zhang, Y.; Xu, Z.-J.; Che, C.-M. Chem. Commun. 2014, 50, 7870.
[48]	Casalnuovo, A. L. WO 2003002255, 2003.
[49]	Chen, J.; Gu, H.-Y.; Zhu, X.-Y.; Nam, W.; Wang, B. Adv. Synth. Catal. 2020, 362, 2976.
[50]	Wartmann, C.; Nandi, S.; Neudörfl, J.-M.; Berkessel, A. Angew. Chem., Int. Ed. 2023, 62, e202306584.
[51]	Sun, S.; Yang, Y.; Zhao, R.; Zhang, D.; Liu, L. J. Am. Chem. Soc. 2020, 142, 19346.
[52]	Cao, M.; Wang, H.; Hou, F.; Zhu, Y.; Liu, Q.; Tung, C.-H.; Liu, L. J. Am. Chem. Soc. 2024, 146, 18396.
[53]	Talsi, E. P.; Bryliakov, K. P. Coord. Chem. Rev. 2012, 256, 1418.
[54]	aOttenbacher, R. V.; Samsonenko, D. G.; Talsi, E. P.; Bryliakov, K. P. Org. Lett. 2012, 14, 4310.
	bShen, D.-Y.; Miao, C.-X.; Wang, S.-F.; Xia, C.-G.; Sun, W. Org. Lett. 2014, 16, 1108.
[55]	Kim, C.; Chen, K.; Kim, J.; Que, L. J. Am. Chem. Soc. 1997, 119, 5964.
[56]	Chen, M. S.; White, M. C. Science 2007, 318, 783.
[57]	Gomez, L.; Garcia-Bosch, I.; Company, A.; Benet-Buchholz, J.; Polo, A.; Sala, X.; Ribas, X.; Costas, M. Angew. Chem., Int. Ed. 2009, 48, 5720.
[58]	Meunier, B. Chem. Rev. 1992, 92, 1411.
[59]	Wang, B.; Miao, C.; Wang, S.; Xia, C.; Sun, W. Chem.-Eur. J. 2012, 18, 6750. doi: 10.1002/chem.201103802 pmid: 22532506
[60]	Font, D.; Canta, M.; Milan, M.; Cusso, O.; Ribas, X.; Gebbink, R. J. M. K.; Costas, M. Angew. Chem., Int. Ed. 2016, 55, 5776.
[61]	Canta, M.; Font, D.; Gomez, L.; Ribas, X.; Costas, M. Adv. Synth. Catal. 2014, 356, 818.
[62]	Dantignana, V.; Milan, M.; Cussó, O.; Company, A.; Bietti, M.; Costas, M. ACS Cent. Sci. 2017, 3, 1350.
[63]	Lee, M.; Sanford, M. S. J. Am. Chem. Soc. 2015, 137, 12796.
[64]	Ottenbacher, R. V.; Talsi, E. P.; Rybalova, T. V.; Bryliakov, K. P. ChemCatChem 2018, 10, 5323.
[65]	Qiu, B.; Xu, D.; Sun, Q.; Miao, C.; Lee, Y.-M.; Li, X.-X.; Nam, W.; Sun, W. ACS Catal. 2018, 8, 2479.
[66]	Qiu, B.; Xu, D.-Q.; Sun, Q.-S.; Lin, J.; Sun, W. Org. Lett. 2019, 21, 618.
[67]	Sun, Q.-S.; Sun, W. Org. Lett. 2020, 22, 9529.
[68]	Ottenbacher, R. V.; Samsonenko, D. G.; Nefedov, A. A.; Talsi, E. P.; Bryliakov, K. P. J. Catal. 2021, 399, 224.
[69]	Ottenbacher, R. V.; Samsonenko, D. G.; Nefedov, A. A.; Bryliakov, K. P. J. Catal. 2022, 415, 12.
[70]	Milan, M.; Bietti, M.; Costas, M. ACS Cent. Sci. 2017, 3, 196.
[71]	(a) Call, A.; Capocasa, G.; Palone, A.; Vicens, L.; Aparicio, E.; Choukairi Afailal, N.; Siakavaras, N.; López Saló, M. E.; Bietti, M.; Costas, M. J. Am. Chem. Soc. 2023, 145, 18094. pmid: 31881152
	(b) Cianfanelli, M.; Olivo, G.; Milan, M.; Klein Gebbink, R. J. M.; Ribas, X.; Bietti, M.; Costas, M. J. Am. Chem. Soc. 2020, 142, 1584. doi: 10.1021/jacs.9b12239 pmid: 31881152
[72]	Palone, A.; Casadevall, G.; Ruiz-Barragan, S.; Call, A.; Osuna, S.; Bietti, M.; Costas, M. J. Am. Chem. Soc. 2023, 145, 15742.
[73]	Vicens, L.; Bietti, M.; Costas, M. Angew. Chem., Int. Ed. 2021, 60, 4740.
[74]	(a) Breit, B.; Bigot, A. Chem. Commun. 2008, 48, 6498. pmid: 30426998
	(b) Smaltz, D. J.; Švenda, J.; Myers, A. G. Org. Lett. 2012, 14, 1812. pmid: 30426998
	(c) Abrams, D. J.; Provencher, P. A.; Sorensen, E. J. Chem. Soc. Rev. 2018, 47, 8925. doi: 10.1039/c8cs00716k pmid: 30426998
[75]	Ottenbacher, R. V.; Bryliakova, A. A.; Kurganskii, V. I.; Prikhodchenko, P. V.; Medvedev, A. G.; Bryliakov, K. P. Chem. Eur. J. 2023, 29, e202302772.
[76]	Chen, J.; Song, W.-X.; Yao, J.-P.; Wu, Z.-M.; Lee, Y.-M.; Wang, Y.; Nam, W.; Wang, B. J. Am. Chem. Soc. 2023, 145, 5456.