Abstract
This study proposes two different methods of photocatalytic-controlled and visible light-induced selective oxidation of pyridiniums with air as the terminal oxidant. The key to these transformations is to choose the appropriate light source and photocatalyst. Pyridiniums are successfully converted into pyrroles through oxygen-mediated cycloaddition, proton-coupled electron transfer (PCET), pyridine ring opening, and recyclization. The other route is that pyridiniums selectively form 4-carbonyl pyridines through free radical rearrangement/aerobic oxidation under the catalysis of cobalt (II).
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Krátký M, Vinšová J. CPD, 2012, 19: 1343–1355
Allais C, Grassot JM, Rodriguez J, Constantieux T. Chem Rev, 2014, 114: 10829–10868
Flisak Z, Sun WH. ACS Catal, 2015, 5: 4713–4724
Guan AY, Liu CL, Sun XF, Xie Y, Wang MA. Bioorg Med Chem, 2016, 24: 342–353
Murakami K, Yamada S, Kaneda T, Itami K. Chem Rev, 2017, 117: 9302–9332
Poynton FE, Bright SA, Blasco S, Williams DC, Kelly JM, Gunnlaugsson T. Chem Soc Rev, 2017, 46: 7706–7756
Madaan P, Tyagi VK. J Oleo Sci, 2008, 57: 197–215
Kakehi A. Heterocycles, 2012, 85: 1529–1577
Bull JA, Mousseau JJ, Pelletier G, Charette AB. Chem Rev, 2012, 112: 2642–2713
Bertuzzi G, Bernardi L, Fochi M. Catalysts, 2018, 8: 632–666
Sowmiah S, Esperança JMSS, Rebelo LPN, Afonso CAM. Org Chem Front, 2018, 5: 453–493
Yamada S. Chem Rev, 2018, 118: 11353–11432
Chen Y, Lu LQ, Yu DG, Zhu CJ, Xiao WJ. Sci China Chem, 2019, 62: 24–57
Ladenburg A. Ber, 1883, 16
Claret PA, Williams GH. J Chem Soc C, 1969, 146
Staveness D, Bosque I, Stephenson CRJ. Acc Chem Res, 2016, 49: 2295–2306
Romero KJ, Galliher MS, Pratt DA, Stephenson CRJ. Chem Soc Rev, 2018, 47: 7851–7866
Proctor RSJ, Phipps RJ. Angew Chem Int Ed, 2019, 58: 13666–13699
He FS, Ye S, Wu J. ACS Catal, 2019, 9: 8943–8960
Correia JTM, Fernandes VA, Matsuo BT, C.Delgado JA, de Souza WC, Paixão MW. Chem Commun, 2020, 56: 503–514
Rössler SL, Jelier BJ, Magnier E, Dagousset G, Carreira EM, Togni A. Angew Chem Int Ed, 2020, 59: 9264–9280
Klauck FJR, James MJ, Glorius F. Angew Chem Int Ed, 2017, 56: 12336–12339
Basch CH, Liao J, Xu J, Piane JJ, Watson MP. J Am Chem Soc, 2017, 139: 5313–5316
Liu WD, Xu GQ, Hu XQ, Xu PF. Org Lett, 2017, 19: 6288–6291
Jelier BJ, Tripet PF, Pietrasiak E, Franzoni I, Jeschke G, Togni A. Angew Chem Int Ed, 2018, 57: 13784–13789
Miyazawa K, Ochi R, Koike T, Akita M. Org Chem Front, 2018, 5: 1406–1410
Barthelemy AL, Tuccio B, Magnier E, Dagousset G. Angew Chem Int Ed, 2018, 57: 13790–13794
Ociepa M, Turkowska J, Gryko D. ACS Catal, 2018, 8: 11362–11367
Wu J, He L, Noble A, Aggarwal VK. J Am Chem Soc, 2018, 140: 10700–10704
Bao X, Wang Q, Zhu J. Angew Chem Int Ed, 2019, 58: 2139–2143
Klauck FJR, Yoon H, James MJ, Lautens M, Glorius F. ACS Catal, 2019, 9: 236–241
Yu XY, Chen JR, Xiao WJ. Chem Rev, 2021, 121: 506–561
Yuan F, Yan D, Gao P, Shi D, Xiao W, Chen J. ChemCatChem, 2021, 13: 543–547
Hu RB, Sun S, Su Y. Angew Chem Int Ed, 2017, 56: 10877–10880
Zhou W, Miura T, Murakami M. Angew Chem Int Ed, 2018, 57: 5139–5142
Kim N, Lee C, Kim T, Hong S. Org Lett, 2019, 21: 9719–9723
Buquoi JQ, Lear JM, Gu X, Nagib DA. ACS Catal, 2019, 9: 5330–5335
Jeon J, He YT, Shin S, Hong S. Angew Chem Int Ed, 2020, 59: 281–285
Xu G, Chen P, Liu P, Tang S, Zhang X, Sun J. Angew Chem Int Ed, 2019, 58: 1980–1984
Jung S, Lee H, Moon Y, Jung HY, Hong S. ACS Catal, 2019, 9: 9891–9896
Kim I, Kang G, Lee K, Park B, Kang D, Jung H, He YT, Baik MH, Hong S. J Am Chem Soc, 2019, 141: 9239–9248
Moon Y, Park B, Kim I, Kang G, Shin S, Kang D, Baik MH, Hong S. Nat Commun, 2019, 10: 4117
Mathi GR, Jeong Y, Moon Y, Hong S. Angew Chem Int Ed, 2020, 59: 2049–2054
Rammal F, Gao D, Boujnah S, Hussein AA, Lalevée J, Gaumont AC, Morlet-Savary F, Lakhdar S. ACS Catal, 2020, 10: 13710–13717
Ghogare AA, Greer A. Chem Rev, 2016, 116: 9994–10034
Liu Q, Wu LZ. Natl Sci Rev, 2017, 4: 359–380
Zhang X, Rakesh KP, Ravindar L, Qin HL. Green Chem, 2018, 20: 4790–4833
Zhang Y, Schilling W, Das S. ChemSusChem, 2019, 12: 2898–2910
Poon T, Sivaguru J, Franz R, Jockusch S, Martinez C, Washington I, Adam W, Inoue Y, Turro NJ. J Am Chem Soc, 2004, 126: 10498–10499
Zhang C, Jiao N. J Am Chem Soc, 2010, 132: 28–29
Yu Q, Zhang Y, Wan JP. Green Chem, 2019, 21: 3436–3441
Ohkoshi S, Ohhata K, Okumura K, Kajitani M, Sugiyama T, Sakaguchi Y, Nakamura J, Hayashi H, Sugimori A. Chem Lett, 1992, 21: 715–718
Titskii GD, Mitchenko ES, Gaidash TS. Theor Exp Chem, 2010, 46: 239–242
Ramette RW, Sandell EB. J Am Chem Soc, 1956, 78: 4872–4878
Best QA, Xu R, McCarroll ME, Wang L, Dyer DJ. Org Lett, 2010, 12: 3219–3221
Yoshioka E, Kohtani S, Jichu T, Fukazawa T, Nagai T, Kawashima A, Takemoto Y, Miyabe H. J Org Chem, 2016, 81: 7217–7229
Cukier RI, Nocera DG. Annu Rev Phys Chem, 1998, 49: 337–369
Formosinho S, Barroso M. Proton-Coupled Electron Transfer: A Carrefour of Chemical Reactivity Traditions. Cambridge: Royal Society of Chemistry, 2012
Weinberg DR, Gagliardi CJ, Hull JF, Murphy CF, Kent CA, Westlake BC, Paul A, Ess DH, McCafferty DG, Meyer TJ. Chem Rev, 2012, 112: 4016–4093
Gentry EC, Knowles RR. Acc Chem Res, 2016, 49: 1546–1556
Wang H, Wang Z, Huang H, Tan J, Xu K. Org Lett, 2016, 18: 5680–5683
Harrowven DC, Sutton BJ. Progress in Heterocyclic Chemistry. Southampton: University of Southampton, 2005
Proctor RSJ, Davis HJ, Phipps RJ. Science, 2018, 360: 419–422
Feng A, Yang Y, Liu Y, Geng C, Zhu R, Zhang D. J Org Chem, 2020, 85: 7207–7217
Acknowledgements
This work was supported by the National Natural Science Foundation of China (22061003, 21861006), the Guangxi Natural Science Foundation of China (2016GXNSFEA380001, 2019GXNSFAA245027), the Guangxi Key R&D Program (AB18221005), the Science and Technology Major Project of Guangxi (AA17204058-21) and Guangxi Science and Technology Base and Special Talents (guike AD19110027).
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Peng, XJ., He, HP., Liu, Q. et al. Photocatalyst-controlled and visible light-enabled selective oxidation of pyridinium salts. Sci. China Chem. 64, 753–760 (2021). https://doi.org/10.1007/s11426-020-9958-6
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DOI: https://doi.org/10.1007/s11426-020-9958-6