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Synlett 2022; 33(15): 1551-1555
DOI: 10.1055/a-1867-7228
DOI: 10.1055/a-1867-7228
letter
Visible-Light-Mediated Direct Amidation of Arenes and Heteroarenes with N-Aminopyridinium Salts
This work was supported by the National Natural Science Foundation of China (NSFC) (Project Nos. 22078045 and 21176039).
Abstract
A novel photoinduced strategy has been developed for the C–H amidation of aromatics and heteroaromatics by using benzamide radicals with free NH groups generated from N-amidopyridinium salts under visible-light irradiation. The new mode of activation of N-amidopyridinium salts proceeds efficiently under mild conditions to give various benzamide derivatives with free NH groups. In addition, oxazoline analogues, synthesized by the reaction with styrene, demonstrate a substantial range of prospective applications for this versatile protocol.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1867-7228.
- Supporting Information
Publication History
Received: 29 April 2022
Accepted after revision: 02 June 2022
Accepted Manuscript online:
02 June 2022
Article published online:
07 July 2022
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References and Notes
- 1a Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
- 1b Mahesh S, Tang K.-C, Raj M. Molecules 2018; 23: 2615
- 2a Navickiene HM. D, Miranda JE, Bortoli SA, Kato MJ, Bolzani VS, Furlan M. Pest Manag. Sci. 2007; 63: 399
- 2b Lamberth C, Kempf H.-J, Kriz M. Pest Manag. Sci. 2007; 63: 57
- 3a Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
- 3b Reddy RS, Lagishetti C, Kiran IN. C, You HY, He Y. Org. Lett. 2016; 18: 3818
- 3c Lagishetti C, Banne S, You HY, Tang M, Guo J, Qi N, He Y. Org. Lett. 2019; 21: 5301
- 3d Reddy RS, Zheng SJ, Lagishetti C, You HY, He Y. RSC Adv. 2016; 6: 68199
- 3e You HY, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang XH, Guo J, Wang CH, He Y. J. Org. Chem. 2018; 83: 4119
- 3f Pattabiraman VR, Bode JW. Nature 2011; 480: 471
- 3g Di Paolo JA, Huang T, Balazs M, Barbosa J, Barck KH, Bravo BJ, Carano RA. D, Darrow J, Davies DR, DeForge LE, Diehl L, Ferrando R, Gallion SL, Giannetti AM, Gribling P, Hurez V, Hymowitz SG, Jones R, Kropf JE, Lee WP, Maciejewski PM, Mitchell SA, Rong H, Staker BL, Whitney JA, Yeh S, Young WB, Yu C, Zhang J, Reif K, Currie KS. Nat. Chem. Biol. 2011; 7: 41
- 3h Butler LM, Webb Y, Agus DB, Higgins B, Tolentino TR, Kutko MC, LaQuaglia MP, Drobnjak M, Cordon-Cardo C, Scher HI, Breslow R, Richon VM, Rifkind RA, Marks PA. Clin. Cancer Res. 2001; 7: 962
- 3i Grunberg SM, Koeller JM. Expert Opin. Pharmacother. 2003; 4: 2297
- 3j Bode JW. Curr. Opin. Drug Discovery Dev. 2006; 9: 765
- 3k Cupido T, Tulla-Puche J, Spengler J, Albericio F. Curr. Opin. Drug Discovery Dev. 2007; 10: 768
- 3l Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
- 3m Pettit GR, Melody N, Chapuis J.-C. J. Nat. Prod. 2020; 83: 1571
- 4 Leone G, Torricelli P, Chiumiento A, Facchini A, Barbucci R. J. Biomed. Mater. Res., Part A 2010; 84: 391
- 5a Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
- 5b Lundberg H, Tinnis F, Selander N, Adolfsson H. Chem. Soc. Rev. 2014; 43: 2714
- 5c Han S.-Y, Kim Y.-A. Tetrahedron 2004; 60: 2447
- 5d Dunetz JR, Magano J, Weisenburger GA. Org. Process Res. Dev. 2016; 20: 140
- 5e Katritzky AR, Cai C, Singh SK. J. Org. Chem. 2006; 71: 3375
- 5f Schneider N, Lowe DM, Sayle RA, Tarselli MA, Landrum GA. J. Med. Chem. 2016; 59: 4385
- 5g Zarecki AP, Kolanowski JL, Markiewicz WT. Molecules 2020; 25: 1761
- 5h Massolo E, Pirola M, Benaglia M. Eur. J. Org. Chem. 2020; 2020: 4641
- 6a Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
- 6b Sheehan JC, Hess GP. J. Am. Chem. Soc. 1955; 77: 1067
- 6c Bofill JM, Albericio F. Tetrahedron Lett. 1999; 40: 2641
- 7a Yi X, Hu X. Angew. Chem. Int. Ed. 2019; 58: 4700
- 7b Zhang M, Duan Y, Li W, Xu P, Cheng J, Yu S, Zhu C. Org. Lett. 2016; 18: 5356
- 7c Pandey G, Koley S, Talukdar R, Sahani PK. Org. Lett. 2018; 20: 5861
- 7d Cannalire R, Amato J, Summa V, Novellino E, Tron GC, Giustiniano M. J. Org. Chem. 2020; 85: 14077
- 7e Leung FK.-C, Cui J.-F, Hui T.-W, Kung KK.-Y, Wong M.-K. Asian J. Org. Chem. 2015; 4: 533
- 7f Wang X.-F, Yu S.-S, Wang C, Xue D, Xiao J. Org. Biomol. Chem. 2016; 14: 7028
- 7g Papadopoulos GN, Kokotos CG. J. Org. Chem. 2016; 81: 7023
- 7h Shen G, Khan R, Yang F, Yang Y, Pu D, Gao Y, Zhan Y, Luo Y, Fan B. Asian J. Org. Chem. 2019; 8: 97
- 8 Leow D. Org. Lett. 2014; 16: 5812
- 9 Brachet E, Ghosh T, Ghosh I, König B. Chem. Sci. 2015; 6: 987
- 10a Tower SJ, Hetcher WJ, Myers TE, Kuehl NJ, Taylor MT. J. Am. Chem. Soc. 2020; 142: 9112
- 10b Moon Y, Lee W, Hong S. J. Am. Chem. Soc. 2020; 142: 124209
- 10c Im H, Choi W, Hong S. Angew. Chem. Int. Ed. 2020; 59: 17511
- 10d Liu W.-D, Xu G.-Q, Hu X.-Q, Xu P.-F. Org. Lett. 2017; 19: 6288
- 10e Yu W.-L, Chen J.-Q, Wei Y.-L, Wang Z.-Y, Xu P.-F. Chem. Commun. 2018; 54: 1948
- 10f Miyazawa K, Koike T, Akita M. Chem. Eur. J. 2015; 21: 11677
- 10g Miyazawa K, Koike T, Akita M. Tetrahedron 2016; 72: 7813
- 10h Goliszewska K, Rybicka-Jasińska K, Szurmak J, Gryko D. J. Org. Chem. 2019; 84: 15834
- 10i Zeppuhar AN, Falvey DE. J. Org. Chem. 2020; 85: 8844
- 10j Zhao Y, Shi C, Su X, Xia W. Chem. Commun. 2020; 56: 5259
- 11 Rössler SL, Jelier BJ, Magnier E, Dagousset G, Carreira EM, Togni A. Angew. Chem. Int. Ed. 2020; 59: 9264
- 12 Greulich TW, Daniliuc CG, Studer A. Org. Lett. 2015; 17: 254
- 13a Szalóki G, Sevez G, Berthet J, Pozzo J.-L, Delbaere S. J. Am. Chem. Soc. 2014; 136: 13510
- 13b Lathrop SP, Pompeo M, Chang W.-TT, Movassaghi M. J. Am. Chem. Soc. 2016; 138: 7763
- 14 Amidation Reaction: General Procedure A vacuum-dried photoreaction tube was charged with N-(benzoylamino)-2,4,6-triphenylpyridinium tetrafluoroborate (1; 0.3 mmol, 1.0 equiv), coupling agent 2 (3 mmol, 10.0 equiv), Ru(bpy)3Cl2 (5 mol%), and anhyd MeCN (3 mL). The tube was then purged with Ar for 10–15 min, then sealed. The mixture was then stirred and uniformly irradiated by a 30 W blue-light lamp 24 h until the starting material was completely consumed. All volatiles were removed from the resulting mixture in a rotary evaporator under reduced pressure and the crude product was purified by column chromatography. 1-Benzoyl-2-methyl-4-phenyl-4,5-dihydro-1H-imidazole (3n); Typical Procedure for a [3+2]-Annulation Reaction A vacuum-dried photoreaction tube was charged with N-(benzoylamino)-2,4,6-triphenylpyridinium tetrafluoroborate (1; 0.3 mmol, 1.0 equiv), styrene (2n; 0.3 mmol, 1.0 equiv), Ru(bpy)3(PF6)2 (5 mol%), and anhyd MeCN (3 mL, 10 equiv). The tube was then purged with Ar for 10–15 min, then sealed. The mixture was then stirred and uniformly irradiated by a 30 W blue-light lamp for 24 h. Soon afterward, the resulting mixture was concentrated by vacuum distillation in a rotary evaporator. Column chromatography [silica gel, PE–EtOAc (2:1)] gave a pale yellow oily liquid; yield: 70.7%; Rf = 0.3 (PE–EtOAc). 1H NMR (600 MHz, CDCl3): δ = 7.48 (d, J = 7.2 Hz, 2 H), 7.43 (t, J = 7.4 Hz, 1 H), 7.36 (t, J = 7.5 Hz, 2 H), 7.28 (t, J = 7.5 Hz, 2 H), 7.22 (d, J = 7.3 Hz, 1 H), 7.20 (s, 2 H), 5.04 (t, J = 8.8 Hz, 1 H), 4.20 (t, J = 10.3 Hz, 1 H), 3.70 (dd, J = 10.6, 8.2 Hz, 1 H), 2.28 (s, 3 H). 13C NMR (151 MHz, CDCl3): δ = 168.66, 159.34, 141.69, 135.96, 131.31, 128.81, 128.60, 127.69, 127.39, 126.49, 67.20, 56.75, 18.67. HRMS (ESI): m/z [M + H]+ calcd for C17H17N2O: 265.1336; found: 265.1340.