Citation: Yuan Jin-Wei, Qu Ling-Bo. KMnO₄-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids[J]. Chinese Chemical Letters, ;2017, 28(5): 981-985. doi: 10.1016/j.cclet.2017.01.016 shu

KMnO₄-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids

Yuan Jin-Wei ^, ,
Qu Ling-Bo

School of Chemistry & Chemical Engineering, Henan University of Technology, Academician Workstation for Natural Medicinal Chemistry of Henan Province, Zhengzhou 450001, China

Corresponding author: Yuan Jin-Wei, yuanjinweigs@126.com
Received Date: 7 December 2016
Revised Date: 12 January 2017
Accepted Date: 16 January 2017
Available Online: 2 May 2017

Figures(4)

Direct C-H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnO₄ as the sole and efficient oxidative system. This method provides an efficient protocol to construct regioselectively 2-arylquinoline N-oxides via radical cross-coupling reaction in moderated to good yields under mild conditions.
- Quinoline N-oxide,
- Arylboronic acid,
- KMnO₄-mediated,
- Radical reaction,
- Arylation
1. [1]
  Vshyvenko S., Reisenauer M.R., Reisenauer S.. Synthesis and biological evaluation of unnatural derivatives of narciclasine:7-aza-nornarciclasine and its N-oxide[J]. Bioorg. Med. Chem. Lett., 2014(24):4236-4238.
2. [2]
  Tahar R., Vivas L., Basco L.. Indolone-N-oxide derivatives:in vitro activity against fresh clinical isolates o plasmodium falciparum. stage specificity and in vitro interactions with established antimalarial drugs[J]. J. Antimicrob. Chemother., 2011(66):2566-2572.
3. [3]
  Werbel L.M., Kersten S.J., Tumer W.R.. Structure-activity relationships of antimalarial indolo[3, 2-c]quinolines[1.2][J]. Eur. J. Med. Chem., 1993(28):837-852.
4. [4]
  Andreev V.P., Korvacheva E.G., Nizhnik Y.P.. Effect of pyridine and quinolilne Noxides on microsomal Na. K-ATPase activity[J]. Pharm. Chem. J., 2006(40):347-348.
5. [5]
  Smith P.W., Wyman P.A., Lovell P.. New quinoline NK₃ receptor antagonists with CNS activity[J]. Bioorg. Med. Chem. Lett., 2009(19):837-840.
6. [6]
  Rodrigues T., Reker D., Kunze J.. Revealing the macromolecular targets of fragment-like natural products[J]. Angew. Chem. Int. Ed., 2015(54):10516-10520.
7. [7]
  Strekowski L., Say M., Henary M.. Synthesis and activity of substituted 2-phenyl quinoline-4-amines. antagonists of immunostimulatory CpGoligodeoxynucleotides[J]. J. Med. Chem., 2003(46):1242-1249.
8. [8]
  Kumar R., Kumar I., Sharma R.. Catalyst and solvent-free alkylation of quinoline N-oxides with olefins:a direct access to quinoline-substituted α-hydroxy carboxylic derivatives[J]. Org. Biomol. Chem., 2016(14):2613-2617.
9. [9]
  Zhao J.J., Li P., Xia C.G.. Metal-free regioselective C-3 nitrotion of quinoline N-oxides with tert-butyl nitrite[J]. RSC Adv., 2015(5):32835-32838.
10. [10]
  Sun K., Chen X.L., Li X.. H-phosphonate-mediated sulfonylation of heteroaromatic N-oxides:a mild and metal-free one-pot synthesis of 2-sulfonyl quinolines/pyridines[J]. Chem. Commun., 2015(51):12111-12114.
11. [11]
  Suzuki A.. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. 1995-1998[J]. J. Organomet. Chem., 1999(576):147-168.
12. [12]
  Hassan J., Sevignon M., Gozzi C.. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction[J]. Chem. Rev., 2002(102):1359-1469.
13. [13]
  Chemler S.R., Trauner D., Danishefsky S.J.. The B-alkyl Suzuki-Miyaura crosscoupling reaction:development, mechanistic study. and applications in natural product synthesis[J]. Angew. Chem. Int. Ed., 2001(40):4544-4568.
14. [14]
  Vuoti S., Autio J., Laitila M.. Palladium-catalyzed Suzuki-Miyaura crosscoupling of various aryl halides using ortho-alkyl-substituted arylphosphanes and (ortho-alkylphenyl) alkylphosphanes under microwave heating[J]. Eur. J. Inorg. Chem., 2008(2008):397-407.
15. [15]
  Zhou J., Zhang Q.F., Zhao W.H.. Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of 3-trifluoromethylthioquinolines[J]. Org. Biomol. Chem., 2016(14):6937-6941.
16. [16]
  Ali N.M., McKillop A., Mitchell M.B.. Palladium-catalysed cross-coupling reactions of arylboronic acids with P-deficient heteroaryl chlorides[J]. Tetrahedron, 1992(48):8117-8126.
17. [17]
  Jung J.Y., Taher A., Hossain S.. Highly active heterogeneous palladium catalyst for the Suzuki reaction of heteroaryl chlorides[J]. Bull. Korean Chem. Soc., 2010(31):3010-3012.
18. [18]
  Tagata T., Nishida M.. The direct synthesis of 3-amino-2-phenylpyridine by using palladium charcoal was reported[J]. J. Org. Chem., 2003(68):9412-9415.
19. [19]
  Kuriyama M., Natsuo S., Shinozawa M.. Ether-imidazolium carbenes for Suzuki-Miyaura cross-coupling of heteroaryl chlorides with aryl/heteroarylboron reagents[J]. Org. Lett., 2013(15):2716-2719.
20. [20]
  Malacea R., Chahdoura F., Devillard M.. ortho-(Dimesitylboryl) phenylphosphines:positive boryl effect in the palladium-catalyzed SuzukiMiyaura coupling of 2-chloropyridines[J]. Adv. Synth. Catal., 2013(355):2274-2284.
21. [21]
  Lee D.H., Choi M., Yu B.W.. Expanded heterogeneous Suzuki-Miyaura coupling reactions of aryl and heteroaryl chlorides under mild conditions[J]. Adv. Synth. Catal., 2009(351):2912-2920.
22. [22]
  Arumugam V., Kaminsky W., Nallasamy D.. ONO pincer type Pd(Ⅱ) complexes:synthesis. crystal structure and catalytic activity towards C-2 arylation of quinoline scaffolds[J]. RSC Adv., 2015(5):77948-77957.
23. [23]
  Seiple I.B., Su S., Rodriguez R.A.. Direct C-H arylation of electron-deficient heterocylces with arylboronic acids[J]. J. Am. Chem. Soc., 2010(132):13194-13196.
24. [24]
  Cho S.H., Hwang S.J., Chang S.. Palladium-catalyzed C-H functionalization of pyridine N-oxides:highly selective alkenylation and direct arylation with unactivated arenes[J]. J. Am. Chem. Soc., 2008(130):9254-9256.
25. [25]
  Ackermann L., Fenner S.. Direc arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates[J]. Chem. Commun., 2011(47):430-432.
26. [26]
  Duric S., Tzschucke C.. Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N-oxides[J]. Org. Lett., 2011(13):2310-2313.
27. [27]
  Campeau L.C., Stuart D.R., Leclerc J.P.. Palladium-catalyzed direct arylation of azine and azole N-oxides:reaction development[J]. J. Am. Chem. Soc, 2009(131):3291-3306.
28. [28]
  Wu Z.Y., Pi C., Cui X.L.. Direct C-2 alkylation of quinoline N-oxides with ethers via palladium-catalyzed dehydrogenative cross-coupling reaction[J]. Adv. Synth. Catal., 2013(355):1971-1976.
29. [29]
  Kianmehr E., Faghih N., Karaji S.. Copper-catalyzed crossdehydrogenative coupling of pyridine N-oxides with cyclic ethers[J]. J. Organomet. Chem., 2016(801):10-13.
30. [30]
  Chen X.P., Cui X.L., Wu Y.J.. C8-selective acylation of quinoline N-oxides with α-oxocarboxylic acids via palladium-catalyzed regioselective C-H bond activation[J]. Org. Lett., 2016(18):3722-3725.
31. [31]
  Chen X.P., Cui X.L., Wu Y.J.. One-pot approach to 8-acylated 2-quinolinones via palladium-catalyzed regioselective acylation o quinoline N-oxides[J]. Org. Lett., 2016(18):2411-2414.
32. [32]
  Mai W.P., Yuan J.W., Li Z.C.. Silver-catalyzed 2-pyridyl arylation of pyridine N-oxides with arylboronic acids at room temperature[J]. Synlett, 2012(23):145-149.
33. [33]
  Li M.L., Li X., Chang H.H.. Palladium-catalyzed direct C-H arylation of pyridine N-oxides with potassium aryl-and heteroaryltrifluoroborates[J]. Org. Biomol. Chem., 2016(14):2421-2426.
34. [34]
  Shen Y., Chen J.X., Liu M.C.. Copper-catalyzed direc C-H arylation of pyridine N-oxides with arylboronic esters:one-pot synthesis of 2-arylpyridines[J]. Chem. Commun., 2014(50):4292-4295.
35. [35]
  Bering L., Antonchick A.P.. Regioselective metal-free cross-coupling of quinoline N-oxides with boronic acids[J]. Org. Lett., 2015(17):3134-3137.
36. [36]
  Wang J., Wang S., Wang G.. Iron-mediated direct arylation with arylboronicacids throughan arylradicaltransfer pathway[J]. Chem. Commun., 2012(48):11769-11771.
37. [37]
  Fujiwara Y., Domingo V., Seiple I.B.. Practical C-H functionalization of quinines with boronic acids[J]. J. Am. Chem. Soc., 2011(133):3292-3295.
38. [38]
  Arghya D., Srimanta M., Arun M.. Iron-catalyzed direct C-H arylation of heterocycles and quinines with arylboronic acids[J]. Eur. J. Org. Chem., 2013(2013):5251-5256.
39. [39]
  Parvinder P.S., Sravan Kumar A., Mahipal Y.. Iron-catalyzed crosscoupling of electron-deficient heterocycles and quinine with organoboron species via innate C-H functiionalization:application in total synthesis of pyrazine alkaloid botryllazine A[J]. J. Org. Chem., 2013(78):2639-2648.
40. [40]
  Ilangovan A., Polu A., Satish G.. K₂S₂O₈-mediated metal-free direct C-H functionalization of quinines using arylboronic acids[J]. Org. Chem. Front., 2015(2):1616-1620.
41. [41]
  Guchhait S.K., Kashyap M., Saraf S.. Direct C-H bond arylation of (hetero)arenes with aryl and heteroarylboronic acids[J]. Synthesis, 2010(7):1166-1170.
42. [42]
  Wang H., Yu Y., Hong X.H.. Mn(Ⅱ)/O₂-promoted oxidative annulations of vinyl isocyanides with boronic acids:synthesis of multi-substituted isoquinolines[J]. Chem. Commun., 2014(50):13485-13488.
43. [43]
  Liu D., Li Y.X., Qi X.T.. Nickel-catalyzed selective oxidative radical crosscoupling:an effective strategy for inert Csp³H functionalizaiton[J]. Org. Lett., 2015(17):998-1001.
44. [44]
  Demir A.S., Reis Ö., Emrullahoglu M.. Generation of aryl radicals from arylboronic acids by manganese(Ⅲ) acetate:synthesis of biaryls and heterobiaryls[J]. J. Org. Chem., 2003(68):578-580.
45. [45]
  Demir A.S., Findik H.. Potassium permanganate/carboxylic acid/organic solvent:a powerful reagent for enone oxidation and aryl couling reactions[J]. Tetrahedron, 2008(64):6196-6201.
46. [46]
  Demir A.S., Findik H., Saygili N.. Manganese(Ⅲ) acetate-mediated synthesis of biarylsunder microwave irradiation[J]. Tetrahedron, 2010(66):1308-1312.
47. [47]
  Yuan J.W., Yang L.R., Yin Q.Y.. KMnO₄/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids[J]. RSC Adv., 2016(6):35936-35944.
48. [48]
  Tobisu M., Koh K., Furukawa T.. Modular synthesis of phenanthridine derivatives by oxidative cycliaztion of 2-isocyanobiphenyls with organoboron reagents[J]. Angew. Chem. Int. Ed., 2012(51):11363-11366.
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KMnO4-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids

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通讯作者: 陈斌, bchen63@163.com

KMnO₄-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids