Application of α-Aminoalkyl Radical in Visible Light Catalysis

doi:10.6023/cjoc202005055

Abstract

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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 63

Figure 1. Several common visible light catalysts

Scheme 1. Formation of α-aminoalkyl radical

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

. Reaction of triethylamine with chlorobenzothiazole

. Coupling reaction of α-aminoalkyl radical with benzothiazole

. Synthesis of benzylamine heterocyclic compounds

. Decarboxylation coupling reaction of haloarenes with amino carboxylic acid

. Synthesis of chiral benzylamine

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

Scheme 10. Synthesis of aminomethyl compounds

. Decarboxylation coupling reaction of arylsulfonate with amino carboxylic acid

Scheme 12. Coupling reaction using solid phosphoric acid as catalyst

Scheme 13. Alkylation catalyzed by dye-sensitized semiconductor

Scheme 14. Synthesis of JAK2 inhibitor LY2784544

. Synthesis of α-cyclobutylamine

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

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

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

. Synergistic catalytic reaction of chiral phosphonic acid and DPZ

. Synthesis of chiral amino tertiary alcohol derivatives

Scheme 21. Reaction of vinyl sulphone with tertiary amines

. 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.

. 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

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

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

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

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

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

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

. Reaction of α-silylamine in heterogeneous photocatalysis

. Reaction of α-aminoalkyl radical in heterogeneous photocatalysis

Scheme 32. Chiral addition reaction of α-silylamine

Scheme 33. Synthesis of macrocyclic compounds

Scheme 34. Reaction of N-dimethylaniline with maleimide

. Addition reaction by energy transfer process

. Addition reaction achieved by EDA complex

Scheme 37. Synthesis of an unnatural amino acid

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

Scheme 39. Intramolecular addition reaction

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

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

. Reaction of α-aminoalkyl radical with allene

. Reaction of α-aminoalkyl radical with alkenyl pyridine

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

. Reaction of α-aminoalkyl radical with alkenes

Scheme 46. Reaction of alkenes with amino carboxylic acid

. Intramolecular radical cyclization

. Addition reaction of quinuclidine as HAT catalyst

Scheme 49. Synthesis of N-heterospirocycles

Scheme 50. Reaction of α-aminoalkyl radical with azodicarboxylate

Scheme 51. Reaction of α-aminoalkyl radical with isocyanate

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

. Addition reaction of α-aminoalkyl radical to imine

. Reaction of α-silylamine with imine

Scheme 56. Chiral addition reaction of α-aminoalkyl radical

. Chiral addition reaction of α-aminoalkyl radical

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

. Addition reaction of α-aminoalkyl radicals to alkynes

. Addition of aromatic ring

. α-Aminoalkyl radical as halogen atom transfer reagent

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

References 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

α-氨基烷基自由基在可见光催化中的应用