Site-selective benzylic C-H oxidation through mediated electrolysis

doi:10.1016/S1872-2067(24)60139-7

Abstract

Abstract: A novel strategy for site-selective benzylic C-H oxidation has been developed through mediated electrolysis. A bulky maleimide N-oxyl radical (MINO) generated by proton-coupled electrochemical oxidation of N-hydroxymaleimide (NHMI), serves as a hydrogen atom-transfer mediator. Good-to-excellent site selectivity was observed among different substrates, providing a practical approach for site-selective benzylic C-H oxidation. Additionally, the hydrogen-atom transfer mechanism for C-H electrochemical oxidation allows the oxidation to proceed at much lower anode potentials relative to direct electrolysis and with minimal reliance on the substrate's electronic properties.

Key words: Organic electrochemistry, Hydrogen atom transfer, Site-selective oxidation, N-Hydroxymaleimide, Radical oxidation

Yi-Fan Xi, Rui-Xing Gao, Ping Fang, Ya-Ping Han, Cong Ma, Tian-Sheng Mei. Site-selective benzylic C-H oxidation through mediated electrolysis[J]. Chinese Journal of Catalysis, DOI: 10.1016/S1872-2067(24)60139-7.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(24)60139-7

References

[1] V. A. Adamian, W. H.Gong, in: Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives, S. S. Stahl, P. L. Alsters, Eds., Wiley-VCH, 2016, 41-66.
[2] H. Sterckx, B. Morel, B. U. W.Maes,Angew. Chem. Int. Ed., 2019, 58, 7946-7970.
[3] I. Bakanas, R. F. Lusi, S. Wiesler, J. H. Cooke, R. Sarpong,Nat. Rev. Chem., 2023, 7, 783-799.
[4] A. N. Campbell, S. S. Stahl,Acc. Chem. Res., 2012, 45, 851-863.
[5] E. Roduner, W. Kaim, B. Sarkar, V. B. Urlacher, J. Pleiss, R. Gläser, W.-D. Einicke, G.A. Sprenger, U. Beifuß, E. Klemm, C. Liebner, H. Hieronymus, S.-F. Hsu, B. Plietker, S. Laschat,ChemCatChem, 2013, 5, 82-112.
[6] K. Chen, J. M. Richter, P. S. Baran,J. Am. Chem. Soc. 2008, 130, 7247-7249.
[7] J. De Houwer, K. A. Tehrani, B. U. W.Maes,Angew. Chem. Int. Ed., 2012, 51, 2745-2748.
[8] H. Sterckx, C. Sambiagio, V. M.-Navarrete, B. U. W.Maes,Adv. Synth. Catal., 2017, 359, 3226-3236.
[9] H. Sterckx, J. D. Houwer, C. Mensch, I. Caretti, K. A. Tehrani, W. A. Herrebout, S. V. Doorslaer, B. U. W.Maes,Chem. Sci., 2015, 7, 346-357.
[10] Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama, Y. Nishiyama,J. Org. Chem., 1995, 60, 3934-3935.
[11] Y. Ishii, S. Sakaguchi, T. Iwahama,Adv. Synth. Catal., 2001, 343, 393-427.
[12] T. Iwahama, K. Syojyo, S. Sakaguchi, Y. Ishii,Org. Process Res. Dev. 1998, 2, 255-260.
[13] J. Ozawa, M. Tashiro, J. Ni, K. Oisaki, M. Kanai,Chem. Sci., 2016, 7, 1904-1909.
[14] J. Ni, J. Ozawa, K. Oisaki, M. Kanai,Org. Biomol. Chem., 2016, 14, 4378-4381.
[15] M. S. Chen, M. C. White,Science, 2007, 318, 783-787.
[16] C. Einhorn, J. Einhorn, C. Marcadal-Abbadi, J.-L. Pierre,J. Org. Chem., 1999, 64, 4542-4546.
[17] M. Nechab, D. N. Kumar, C. Philouze, C. Einhorn, J. Einhorn,Angew. Chem. Int. Ed., 2007, 46, 3080-3083.
[18] Y. Kawamata, M. Yan, Z. Liu, D.-H. Bao, J. Chen, J. T. Starr, P. S. Baran,J. Am. Chem. Soc., 2017, 139, 7448-7451.
[19] M. Saito, Y. Kawamata, M. Meanwell, R. Navratil, D. Chiodi, E. Carlson, P. Hu, L. Chen, S. Udyavara, C. Kingston, M. Tanwar, S. Tyagi, B. P.McKillican, M. G. Gichinga, M. A. Schmidt, M. D. Eastgate, M. Lamberto, C. He, T. Tang, C. A. Malapit, M. S. Sigman, S. D.Minteer, M. Neurock, P. S. Baran,J. Am. Chem. Soc., 2021, 143, 7859-7867.
[20] T. Kato, K. Maruoka,Angew. Chem. Int. Ed., 2020, 59, 14261-14264.
[21] Y. Cao, C. Huang, Q. Lu,Nat. Synth., 2024, 3, 537-544.
[22] L. Zou, X. Wang, S. Xiang, W. Zheng, Q. Lu,Angew. Chem. Int. Ed., 2023, 62, e202301026.
[23] W. Fan, X. Zhao, Y. Deng, P. Chen, F. Wang, G. Liu,J. Am. Chem. Soc., 2022, 144, 21674-21682.
[24] C.-Y. Cai, X.-L. Lai, Y. Wang, H.-H. Hu, J. Song, Y. Yang, C. Wang, H.-C. Xu,Nat. Catal., 2022, 5, 943-951.
[25] Z. Wang, C. Ma, P. Fang, H. Xu, T. Mei,Acta Chim. Sin., 2022, 80, 1115-1134.
[26] P. Xiong, H.-C. Xu,Acc. Chem. Res., 2019, 52, 3339-3350.
[27] T. Noël, Y. Cao, G. Laudadio,Acc. Chem. Res., 2019, 52, 2858-2869.
[28] Y. Wang, S. Dana, H. Long, Y. Xu, Y. Li, N. Kaplaneris, L. Ackermann,Chem. Rev., 2023, 123, 11269-11335.
[29] P. S. Baran, C. Kingston, M. D. Palkowitz, Y. Takahira, J. C. Vantourout, B. K. Peters, Y. A Kawamata,Acc. Chem. Res., 2020, 53, 72-83.
[30] J.-M. Savéant,Chem. Rev., 2008, 108, 2348-2378.
[31] R. Francke, R. D. Little,Chem. Soc. Rev., 2014, 43, 2492-2521.
[32] F. Wang, S. S. Stahl,Acc. Chem. Res., 2020, 53, 561-574.
[33] Y. Yuan, A. Lei,Acc. Chem. Res., 2019, 52, 3309-3324.
[34] L. Ackermann,Acc. Chem. Res., 2020, 53, 84-104.
[35] M. A. Hoque, J. Twilton, J. Zhu, M. D. Graaf, K. C. Harper, E. Tuca, G. A.DiLabio, S. S. Stahl,J. Am. Chem. Soc., 2022, 144, 15295-15302.
[36] M. Rafiee, F. Wang, D. P. Hruszkewycz, S. S. Stahl,J. Am. Chem. Soc., 2018, 140, 22-25.
[37] J. E. Nutting, M. Rafiee, S. S. Stahl,Chem. Rev., 2018, 118, 4834-4885.
[38] M. Masui, T. Ueshima, S. Ozaki,J. Chem. Soc. Chem. Commun., 1983, 479-480.
[39] M. Masui, S. Hara, T. Ueshima, T. Kawaguchi, S. Ozaki,Chem. Pharm. Bull., 1983, 31, 4209-4211.
[40] M. Masui, T. Kawaguchi, S. Ozaki,J. Chem. Soc. Chem. Commun., 1985, 1484-1485.
[41] M. Masui, K. Hosomi, K. Tsuchida, S. Ozaki,Chem. Pharm. Bull., 1985, 33, 4798-4802.
[42] C. Ueda, M. Noyama, H. Ohmori, M. Masui,Chem. Pharm. Bull., 1987, 35, 1372-1377.
[43] R. G. Agarwal, S. C. Coste, B. D. Groff, A. M. Heuer, H. Noh, G. A. Parada, C. F. Wise, E. M. Nichols, J. J. Warren, J. M. Mayer,Chem. Rev., 2022, 122, 1-49.
[44] C. Yang, L.A. Farmer, D.A. Pratt, S. Maldonado, C. R. J.Stephenson,J. Am. Chem. Soc., 2021, 143, 10324-10332.
[45] C. Yang, S. Arora, S. Maldonado, D. A. Pratt, C. R. J.Stephenson,Nat. Rev. Chem., 2023, 7, 653-666.
[46] E. Baciocchi, M. Bietti, C. D’Alfonso, O. Lanzalunga, A. Lapi, M. Salamone,Org. Biomol. Chem., 2011, 9, 4085-4090.
[47] S. Kishioka, A. Yamada,Electrochim. Acta, 2006, 51, 4582-4588.
[48] O. Kushch, I. Hordieieva, K. Novikova, Y. Litvinov, M. Kompanets, A. Shendrik, I. Opeida,J. Org. Chem., 2020, 85, 7112-7124.
[49] M. Nechab, C. Einhorn, J. Einhorn,Chem. Commun., 2004, 1500-1501.
[50] G.da Silva, J. W. Bozzelli,J. Phys. Chem. C, 2007, 111, 5760-5765.
[51] R. Arnaud, A. Milet, C. Adamo, C. Einhorn, J. Einhorn,J. Chem. Soc. Perkin Trans. 2, 2002, 1967-1972.
[52] T. Newhouse, P. S. Baran,Angew. Chem. Int. Ed., 2011, 50, 3362-3374.
[53] C. Yang, L. A. Farmer, E. M.McFee, R. K. Jha, S. Maldonado, D. A. Pratt, C. R. J. Stephenson,Angew. Chem. Int. Ed., 2024, 63, e202315917.
[54] E. J. Horn, B. R. Rosen, Y. Chen, J. Tang, K. Chen, M. D. Eastgate, P. S. Baran,Nature, 2016, 533, 77-81.
[55] D. P. Hruszkewycz, K. C. Miles, O. R. Thiel, S. S. Stahl,Chem. Sci., 2017, 8, 1282-1287.
[56] Y. Wang, Z. Lin, J. C. A.Oliveira, L. Ackermann,J. Org. Chem., 2021, 86, 15935-15945.