α-氨基烷基自由基在可见光催化中的应用

doi:10.6023/cjoc202005055

摘要/Abstract

可见光催化具有成本低及环境友好等特点, 符合绿色化学的要求, 近年来在有机合成领域引起了广泛关注. 其中α-氨基烷基自由基因其具有活性高和易获得等优点, 在可见光催化中占据着重要的位置. 主要综述了该活性自由基在可见光催化中的发展和应用, 并对其未来研究进行了展望.

关键词: 可见光催化, α-氨基烷基自由基, 有机合成, 绿色化学

Because of its low cost and environmental friendliness, visible light catalysis has been widely used in organic synthesis in recent years. Among them, α-aminoalkyl radical plays an important role because of its high activity and accessibility. The development and application of this active radical in visible light catalysis are mainly summarized and its outlook in the future is given.

Key words: visible light catalysis, α-aminoalkyl radical, organic synthesis, green chemistry

引用此文

赵赫, 程冬萍, 许孝良. α-氨基烷基自由基在可见光催化中的应用[J]. 有机化学, 2021, 41(2): 642-660.

He Zhao, Dongping Cheng, Xiaoliang Xu. Application of α-Aminoalkyl Radical in Visible Light Catalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 642-660.

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

分享此文

图/表 63

图1. 常见的几种可见光催化剂

Figure 1. Several common visible light catalysts

图式1. α-氨基烷基自由基的生成方式

Scheme 1. Formation of α-aminoalkyl radical

图式2. 叔胺α位芳基化产物的合成

Scheme 2. Synthesis of α-arylation products of tertiary amines

Scheme 3. 三乙胺与氯代苯并噻唑的反应

. Reaction of triethylamine with chlorobenzothiazole

Scheme 4. α-氨基烷基自由基与苯并噻唑的偶联反应

. Coupling reaction of α-aminoalkyl radical with benzothiazole

Scheme 5. 苄胺杂环类化合物的合成

. Synthesis of benzylamine heterocyclic compounds

Scheme 6. 卤代芳烃与氨基羧酸的脱羧偶联反应

. Decarboxylation coupling reaction of haloarenes with amino carboxylic acid

Scheme 7. 手性苄胺类化合物的合成

. Synthesis of chiral benzylamine

Scheme 8. 手性苄胺类化合物的合成

. Synthesis of chiral benzylamine

图式9. 叔胺和卤代芳烃的三重催化交叉偶联

Scheme 9. Triple catalytic cross-coupling of tertiary amines with haloarenes

图式10. 氨甲基类化合物的合成

Scheme 10. Synthesis of aminomethyl compounds

Scheme 11. 芳基磺酸酯与氨基羧酸的脱羧偶联反应

. Decarboxylation coupling reaction of arylsulfonate with amino carboxylic acid

图式12. 固体磷酸作为催化剂的偶联反应

Scheme 12. Coupling reaction using solid phosphoric acid as catalyst

图式13. 染料敏化半导体参与的烷基化反应

Scheme 13. Alkylation catalyzed by dye-sensitized semiconductor

图式14. JAK2抑制剂LY2784544的合成

Scheme 14. Synthesis of JAK2 inhibitor LY2784544

Scheme 15. α-环丁基胺的合成

. Synthesis of α-cyclobutylamine

Scheme 16. 叔丁基溴与α-氨基烷基自由基的反应

. Reaction of t-butyl bromide with α-aminoalkyl radical

Scheme 17. 基于极性匹配原则下的选择性C(sp3)—H烷基化反应

. Selective C(sp3)—Halkylation via polarity-match- based cross-coupling

图式18. 手性膦酸与DPZ的协同催化反应

Scheme 18. Synergistic catalytic reaction of chiral phosphonic acid and DPZ

Scheme 19. 手性膦酸与DPZ的协同催化反应

. Synergistic catalytic reaction of chiral phosphonic acid and DPZ

Scheme 20. 手性氨基叔醇类衍生物的合成

. Synthesis of chiral amino tertiary alcohol derivatives

图式21. 叔胺与乙烯基砜的反应

Scheme 21. Reaction of vinyl sulphone with tertiary amines

Scheme 22. α-氨基烷基自由基与乙烯基卤化物的反应

. Reaction of α-aminoalkyl radical with vinyl halides 关键性作用的过程为通过烯丙基钯中间体的还原消除来产生烯丙基自由基中间体.

Scheme 23. α-氨基烷基自由基在烯丙位的取代反应

. Allylic substitution reaction of α-aminoalkyl radical 2.5 α-氨基烷基自由基与炔烃的偶联反应

图式24. α-氨基烷基自由基与炔基卤化物的反应

Scheme 24. Reaction of α-aminoalkyl radical with alkynyl halide

图式25. α-氨基烷基自由基对α,β-不饱和酮的加成

Scheme 25. Addition reaction of α,β-unsaturated ketone with α-aminoalkyl radical

图式26. α-硅烷基胺与α,β-不饱和酮类物质的加成

Scheme 26. Addition reaction of α,β-unsaturated ketone with α-silylamine

图式27. α-氨基烷基自由基与α,β-不饱和酮类物质的加成

Scheme 27. Addition reaction of α,β-unsaturated ketone with α-aminoalkyl radical

图式28. α-氨基烷基自由基与α,β-不饱和酮类物质的不对称加成

Scheme 28. Asymmetric addition reaction of α,β-unsaturated ketone with α-aminoalkyl radical

Scheme 29. α-氨基烷基自由基与α,β-不饱和酮类物质的不对称加成

. Asymmetric addition reaction of α,β-unsaturated ketone with α-aminoalkyl radical

Scheme 30. α-硅烷基胺在非均相光催化中的反应

. Reaction of α-silylamine in heterogeneous photocatalysis

Scheme 31. α-氨基烷基自由基在非均相光催化中的反应

. Reaction of α-aminoalkyl radical in heterogeneous photocatalysis

图式32. α-硅烷基胺的手性加成反应

Scheme 32. Chiral addition reaction of α-silylamine

图式33. 大环类化合物的合成方法

Scheme 33. Synthesis of macrocyclic compounds

图式34. N,N-二甲基苯胺与马来酰亚胺的反应

Scheme 34. Reaction of N-dimethylaniline with maleimide

Scheme 35. 能量转移实现的加成反应

. Addition reaction by energy transfer process

Scheme 36. 通过EDA配合物实现的加成反应

. Addition reaction achieved by EDA complex

图式37. 一种非天然氨基酸的合成方法

Scheme 37. Synthesis of an unnatural amino acid

图式38. α-氨基烷基自由基与烯基羧酸酯的反应

Scheme 38. Reaction of α-aminoalkyl radical with alkenyl carboxylate

图式39. 分子内的加成反应

Scheme 39. Intramolecular addition reaction

图式40. α-氨基烷基自由基与烯基腈的反应

Scheme 40. Reaction of α-aminoalkyl radical with vinyl nitrile

Scheme 41. α-氨基烷基自由基与Baylis-Hillman衍生物的反应

. Reaction of α-aminoalkyl radical with Baylis- Hillman derivative

Scheme 42. α-氨基烷基自由基与联烯的反应

. Reaction of α-aminoalkyl radical with allene

Scheme 43. α-氨基烷基自由基与烯基吡啶的反应

. Reaction of α-aminoalkyl radical with alkenyl pyridine

图式44. 2-乙烯基氮杂环化合物与α-氨基烷基自由基的反应

Scheme 44. Reaction of α-aminoalkyl radical with 2-vinylazaarenes

Scheme 45. α-氨基烷基自由基与烯烃的反应

. Reaction of α-aminoalkyl radical with alkenes

图式46. 氨基羧酸与烯烃的反应

Scheme 46. Reaction of alkenes with amino carboxylic acid

Scheme 47. 分子内的自由基环化反应

. Intramolecular radical cyclization

Scheme 48. 奎宁作为HAT催化剂的加成反应

. Addition reaction of quinuclidine as HAT catalyst

图式49. 氮取代螺结构化合物的合成

Scheme 49. Synthesis of N-heterospirocycles

图式50. α-氨基烷基自由基与偶氮二羧酸酯的反应

Scheme 50. Reaction of α-aminoalkyl radical with azodicarboxylate

图式51. α-氨基烷基自由基与异氰酸酯的反应

Scheme 51. Reaction of α-aminoalkyl radical with isocyanate

Scheme 52. β-氨基羟胺类化合物的合成 Synthesis of β-amino hydroxylamines

图式53. α-氨基烷基自由基对亚胺的加成

Scheme 53. Addition reaction of α-aminoalkyl radical to imine

Scheme 54. α-氨基烷基自由基对亚胺的加成

. Addition reaction of α-aminoalkyl radical to imine

Scheme 55. α-硅烷基胺与亚胺的反应

. Reaction of α-silylamine with imine

图式56. α-氨基烷基自由基的手性加成反应

Scheme 56. Chiral addition reaction of α-aminoalkyl radical

Scheme 57. α-氨基烷基自由基的手性加成反应

. Chiral addition reaction of α-aminoalkyl radical

Scheme 58. α-氨基烷基自由基对咪唑并吡啶的加成反应

. Addition reaction of α-aminoalkyl radical to imidazole pyridine 3.3 碳碳叁键上的加成

Scheme 59. α-氨基烷基自由基与炔类物质的加成反应

. Addition reaction of α-aminoalkyl radicals to alkynes

Scheme 60. 芳香环上的加成

. Addition of aromatic ring

Scheme 61. α-氨基烷基自由基作为卤原子转移试剂

. α-Aminoalkyl radical as halogen atom transfer reagent

图式62. α-氨基烷基自由基作为中间体参与的Povarov反应

Scheme 62. Povarov reaction involving α-aminoalkyl radical as intermediates

参考文献 79

[1]	Schmittel M.; Burghart A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550. doi: 10.1002/(ISSN)1521-3773
[2]	Houmam.A. Chem. Rev. 2008, 108, 2180. doi: 10.1021/cr068070x
[3]	Ruiz Espelt, L.; McPherson, I.S.; Wiensch, E.M.; Yoon, T.P. J. Am. Chem. Soc. 2015, 137, 2452. doi: 10.1021/ja512746q
[4]	Dai X.; Cheng D.; Guan B.; Mao W.; Xu X.; Li X. J. Org. Chem. 2014, 79, 7212. doi: 10.1021/jo501097b
[5]	Shi L.; Xia W.J. Chem. Soc. Rev. 2012, 41, 7687. doi: 10.1039/c2cs35203f
[6]	Xuan J.; Xiao W.J. Angew. Chem., Int. Ed. 2012, 51, 6828. doi: 10.1002/anie.201200223
[7]	McNally A.; Prier C.K.; MacMillan D. W. C.Science 2011, 334, 1114. doi: 10.1126/science.1213920
[8]	Miyake Y.; Nakajima K.; Nishibayashi Y. J. Am. Chem. Soc. 2012, 134, 3338. doi: 10.1021/ja211770y
[9]	Chen J.R.; Hu X.Q.; Lu L.Q.; Xiao W.J. Acc. Chem. Res. 2016, 49, 1911. doi: 10.1021/acs.accounts.6b00254
[10]	Yoon U.C.; Mariano P.S. Acc. Chem. Res. 1992, 25, 233. doi: 10.1021/ar00017a005
[11]	Cho D.W.; Yoon U.C.; Mariano P.S. Acc. Chem. Res. 2011, 44, 204. doi: 10.1021/ar100125j
[12]	Nakajima K.; Nojima S.; Nishibayashi Y. Acc. Chem. Res. 2016, 49, 1946. doi: 10.1021/acs.accounts.6b00251
[13]	McNally A.; Prier C.K.; MacMillan D. W. C.Science 2011, 334, 1114. doi: 10.1126/science.1213920
[14]	Singh A.; Arora A.; Weaver J.D. Org. Lett. 2013, 15, 5390. doi: 10.1021/ol402751j
[15]	Dong J.; Xia Q.; Lv X.; Yan C.; Song H.; Liu Y.; Wang Q. Org. Lett. 2018, 20, 5661. doi: 10.1021/acs.orglett.8b02389
[16]	Zuo Z.; MacMillan D. W. C.J. Am. Chem. Soc. 2014, 136, 5257. doi: 10.1021/ja501621q
[17]	Zuo Z.; Ahneman D.T.; Chu L.; Terrett J.A.; Doyle A.G.; Mac- Millan, D. W. C.Science 2014, 345, 437.
[18]	Zuo Z.; Cong H.; Li W.; Choi J.; Fu G.C.; MacMillan D. W. C.J. Am. Chem. Soc. 2016, 138, 1832. doi: 10.1021/jacs.5b13211
[19]	Tellis J.C.; Primer D.N.; Molander G.A. Science 2014, 345, 433.
[20]	El Khatib, M.; Serafim, R. A. M.; Molander, G.A. Angew. Chem., Int. Ed. 2016, 55, 254. doi: 10.1002/anie.201506147
[21]	Shaw.M.H.; Shurtleff, V. W.; Terrett, J. A.; MacMillan, D. W. C.Science 2016, 352, 1304. doi: 10.1126/science.aaf6635
[22]	Remeu C.; Kelly C.B.; Patel N.R.; Molander G.A. ACS Catal. 2017, 7, 6065. doi: 10.1021/acscatal.7b01973
[23]	Fan, L-L.; Jia, J.; Hou, H.; Lefebvre, Q.; Rueping, M.Chem.-Eur. J. 2016, 22, 16437. doi: 10.1002/chem.201604452
[24]	Cheng W.M.; Sang R.; Fu Y. ACS Catal. 2017, 7, 907. doi: 10.1021/acscatal.6b03215
[25]	Ren L.; Cong H. Org. Lett. 2018, 20, 3225. doi: 10.1021/acs.orglett.8b01077
[26]	Douglas J.J.; Cole K.P.; Stephenson C. R. J.J. Org. Chem. 2014, 79, 11631. doi: 10.1021/jo502288q
[27]	Pratt C.J.; Aycock R.A.; King M.D.; Jui N.T. Synlett 2020, 31, 51. doi: 10.1055/s-0039-1690197
[28]	Zhou W.; Cao G.M.; Shen G.; Zhu X.; Gui Y.; Ye J.; Sun L.; Liao L.J.; Yu D.G. Angew. Chem., Int. Ed. 2017, 56, 15683. doi: 10.1002/anie.201704513
[29]	Le C.; Liang Y.F.; MacMillan D.W. C. Nature 2017, 547, 79.
[30]	Li J.; Kong M.; Qiao B.; Lee R.; Zhao X.; Jiang Z. Nat. Commun. 2018, 9, 2445. doi: 10.1038/s41467-018-04885-3
[31]	Zeng G.; Li Y.; Qiao B.; Zhao X.; Jiang Z. Chem. Commun. 2019, 55, 11362. doi: 10.1039/C9CC05304B
[32]	Liu Y.; Liu X.; Li J.; Zhao X.; Qiao B. Jiang Z. Chem. Sci. 2018, 9, 8094. doi: 10.1039/C8SC02948B
[33]	Noble A.; MacMillan D. W. C.J. Am. Chem. Soc. 2014, 136, 11602. doi: 10.1021/ja506094d
[34]	Noble A.; McCarver S.J.; MacMillan D. W. C.J. Am. Chem. Soc. 2015, 137, 624. doi: 10.1021/ja511913h
[35]	Xuan J.; Zeng T.-T.; Feng Z.J.; Deng Q.H.; Chen J.R.; Lu L.Q.; Xiao W.J.; Alper H. Angew. Chem., Int. Ed. 2015, 54, 1625. doi: 10.1002/anie.201409999
[36]	Xie J.; Shi S.; Zhang T.; Mehrkens N.; Rudolph M.; Hashmi A. S. K.Angew. Chem., Int. Ed. 2015, 54, 6046. doi: 10.1002/anie.201412399
[37]	Kohls P.; Jadhav D.; Pandey G.; Reiser O. Org. Lett. 2012, 14, 672. doi: 10.1021/ol202857t
[38]	Espelt L.R.; Wiensch E.M.; Yoon T.P. J. Org. Chem. 2013, 78, 4107. doi: 10.1021/jo400428m
[39]	Miyake Y.; Ashida Y.; Nakajima K.; Nishibayashi Y. Chem. Commun. 2012, 48, 6966. doi: 10.1039/c2cc32745g
[40]	Nakajima K.; Kitagawa M.; Ashida Y.; Miyake Y.; Nishibayashi Y. Chem. Commun. 2014, 50, 8900. doi: 10.1039/C4CC03000A
[41]	Miyazawa K.; Koike T.; Akita M. Adv. Synth. Catal. 2014, 356, 2749. doi: 10.1002/adsc.201400556
[42]	Murphy J.J.; Bastida D.; Paria S.; Fagnoni M.; Melchiorre P. Nature 2016, 532, 218. doi: 10.1038/nature17438 pmid: 27075098
[43]	Lin S.X.; Sun G.J.; Kang Q. Chem. Commun. 2017, 53, 7665. doi: 10.1039/C7CC03650G
[44]	Cai Y.F.; Yu R.T.; Fan, L-L.; Hou, H.; Lefebvre, Q.; Rueping, M.ACS Catal. 2018, 8, 9471. doi: 10.1021/acscatal.8b02937
[45]	Xi Z.W.; Yang L.; Wang D.Y.; Pu C.D.; Shen Y.M.; Wu C.D.; Peng X.G. J. Org. Chem. 2018, 83, 11886. doi: 10.1021/acs.joc.8b01651
[46]	Ruiz Espelt, L.; McPherson, I.S.; Wiensch, E.M.; Yoon, T.P. J. Am. Chem. Soc. 2015, 137, 2452. doi: 10.1021/ja512746q
[47]	McCarver S.J.; Qiao J.X.; Carpenter J.; Borzilleri R.M.; Poss M.A.; Eastgate M.D.; MacMillan D. W. C.Angew. Chem., Int. Ed. 2017, 56, 728. doi: 10.1002/anie.v56.3
[48]	Ju X.; Li D.; Li W.; Yu W. Adv. Synth.Catal. 2012, 354, 3561.
[49]	Guo J.T.; Yang D.C.; Guan Z.; He Y.H. J. Org. Chem. 2017, 82, 1888. doi: 10.1021/acs.joc.6b03034
[50]	Hsu C.W.; Sundén H. Org. Lett. 2018, 20, 2051. doi: 10.1021/acs.orglett.8b00597
[51]	Aycock R, A.; Pratt, C, J.; Jui, N, T.ACS Catal. 2018, 9115.
[52]	Miyake Y.; Nakajima K.; Nishibayashi Y. J. Am. Chem. Soc. 2012, 134, 3338. doi: 10.1021/ja211770y
[53]	Mizoguchi H.; Oikawa H.; Oguri H. Nat. Chem. 2014, 6, 57. doi: 10.1038/nchem.1798 pmid: 24345948
[54]	Zhu S.; Das A.; Bui L.; Zhou H.; Curran D.P.; Rueping M. J. Am. Chem. Soc. 2013, 135, 1823. doi: 10.1021/ja309580a
[55]	Dai X.; Cheng D.; Guan B.; Mao W.; Xu X.; Li X. J. Org. Chem. 2014, 79, 7212. doi: 10.1021/jo501097b
[56]	Dai X.; Mao R.; Guan B.; Xu X.; Li X. RSC Adv. 2015, 5, 55290. doi: 10.1039/C5RA10491B
[57]	Hepburn H.B.; Melchiorre P. Chem. Commun. 2016, 52, 3520. doi: 10.1039/C5CC10401G
[58]	Yin Y.; Dai Y.; Jia H.; Li J.; Bu L.; Qiao B.; Zhao X.; Jiang Z. J. Am. Chem. Soc. 2018, 140, 6083. doi: 10.1021/jacs.8b01575
[59]	Chu L.; Ohta C.; Zuo Z.; MacMillan D. W. C.J. Am. Chem. Soc. 2014, 136, 10886. doi: 10.1021/ja505964r
[60]	Miyazawa K.; Koike T.; Akita M. Adv. Synth. Catal. 2014, 356, 2749. doi: 10.1002/adsc.201400556
[61]	McManus J.B.; Onuska N.P.; Nicewicz D.A. J. Am. Chem. Soc. 2018, 140, 9056. doi: 10.1021/jacs.8b04890
[62]	Grübel M.; Jandl C.; Bach T. Synlett 2019, 30, 1825. doi: 10.1055/s-0039-1690006
[63]	Ashley M.A.; Yamauchi C.; Chu J.C.; Otsuka S.; Yorimitsu H.; Rovis T. Angew. Chem., Int. Ed. 2019, 58, 4002. doi: 10.1002/anie.v58.12
[64]	Flodén N.J.; Trowbridge A.; Willcox D.; Walton S.M.; Kim Y.; Gaunt M.J. J. Am. Chem. Soc. 2019, 141, 8426. doi: 10.1021/jacs.9b03372
[65]	Miyake Y.; Nakajima K.; Nishibayashi Y. Chem.-Eur. J. 2012, 18, 16473. doi: 10.1002/chem.201203066
[66]	Zhou H.; Lu P.; Gu X.; Li P. Org. Lett. 2013, 15, 5646. doi: 10.1021/ol402573j
[67]	Itoh K.; Kato R.; Kinugawa D.; Kamiya H.; Kudo R.; Hasegawa M.; Fujii H.; Suga H. Org. Biomol. Chem. 2015, 13, 8919. doi: 10.1039/C5OB01277E
[68]	Uraguchi D.; Kinoshita N.; Kizu T.; Ooi T. J. Am. Chem. Soc. 2015, 137, 13768. doi: 10.1021/jacs.5b09329
[69]	Fava E.; Millet A.; Nakajima M.; Loescher S.; Rueping M. Angew. Chem., Int. Ed. 2016, 55, 6776. doi: 10.1002/anie.201511235
[70]	Han B.; Li Y.; Yu Y.; Gong L. Nat. Commun. 2019, 10, 3804. doi: 10.1038/s41467-019-11688-7
[71]	Proctor R. S. J.; Davis H.J.; Phipps R.J. Science 2018, 360, 419. doi: 10.1126/science.aar6376
[72]	Liu X.; Liu Y.; Chai G.; Qiao B.; Zhao X.; Jiang Z. Org. Lett. 2018, 20, 6298. doi: 10.1021/acs.orglett.8b02791
[73]	Ji J.; Zhu Z.; Xiao L.; Zhu X.; Le Z. Org. Chem. Front. 2019, 6, 3693. doi: 10.1039/C9QO00935C
[74]	Zhang P.; Xiao T.; Xiong S.; Dong X.; Zhou L. Org. Lett. 2014, 16, 3264. doi: 10.1021/ol501276j
[75]	Miyake Y.; Ashida Y.; Nakajima K.; Nishibayashi Y. Chem.-Eur. J. 2014, 20, 6120. doi: 10.1002/chem.201304731
[76]	Nakajima K.; Ashida Y.; Nojima S.; Nishibayashi Y. Chem. Lett. 2015, 44, 545. doi: 10.1246/cl.150019
[77]	Constantin T.; Zanini M.; Regni A.; Sheikh N.S.; Julia F.; Leonori D. Science 2020, 367, 1021. doi: 10.1126/science.aba2419
[78]	Zhou X.S.; Yan D.M.; Chen J.R. Chem 2020, 6, 823. doi: 10.1016/j.chempr.2020.03.007
[79]	Li J.; Gu Z.; Zhao X.; Qiao B.; Jiang Z. Chem. Commun. 2019, 55, 12916. doi: 10.1039/C9CC07380A