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Synthesis 2023; 55(19): 3113-3120
DOI: 10.1055/a-2096-6841
DOI: 10.1055/a-2096-6841
paper
Synthesis of N-Phenylcarbamate by C–N Coupling Reaction without Metal Participation
Authors
The National Natural Science Foundation of China (Grant No. 21961038), and the Shanghai Cooperation Organization Science and Technology Partnership Program (No. 2022E01049).
Abstract
We have developed a new method for the synthesis of carbamates from amine and hydrazine formate. The reaction occurs in the presence of iodine and tert-butyl hydroperoxide, in which carbazates are produced via alkoxycarbonyl radical formation for cross-coupling reaction. The method exhibits broad functional group tolerance and affords a series of N-phenylcarbamates in moderate to good yields. Remarkably, our approach is metal free and utilizes cheap, readily available raw materials and relatively universal substrates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2096-6841.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 02. April 2023
Angenommen nach Revision: 22. Mai 2023
Accepted Manuscript online:
22. Mai 2023
Artikel online veröffentlicht:
27. Juni 2023
© 2023. Thieme. All rights reserved
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References
- 1a Ghosh AK. J. Org. Chem. 2010; 75: 7967
- 1b Kaul L, Suss R, Zannettino A, Richter K. iScience 2021; 24: 102092
- 2a Ghosh AK. J. Med. Chem. 2015; 58: 2895
- 2b Joshi A, Veron JB, Unge J, Rosenquist A, Wallberg H, Samuelsson B, Hallberg A, Larhed M. J. Med. Chem. 2013; 56: 8999
- 3a Uma Priya K, Venkataramaiah C, Sreedhar NY, Raju CN. RSC Adv. 2021; 11: 3897
- 3b Ding Y, Li Z, Hu W, Feng X, Chen Y, Yan G, Wang Y, Zhu B, Yao W, Zheng L, He M, Gao M, Zhao J. Biomater. Sci. 2021; 9: 6236
- 4a Dozieres-Puyravel B, Nasser H, Bellavoine V, Ilea A, Delanoe C, Auvin S. Dev. Med. Child Neurol. 2020; 62: 581
- 4b Lux A. Dev. Med. Child Neurol. 2020; 62: 541
- 5a Krzywik J, Aminpour M, Janczak J, Maj E, Moshari M, Mozga W, Wietrzyk J, Tuszynski JA, Huczynski A. Eur. J. Med. Chem. 2021; 215: 113282
- 5b Narkhede HI, Dhake AS, Surana AR. Bioorg. Chem. 2022; 124: 105832
- 6 Mata G, do Rosario VE, Iley J, Constantino L, Moreira R. Bioorg. Med. Chem. 2012; 20: 886
- 7a Hellstrom AK, Bordes R. J. Colloid Interface Sci. 2019; 536: 722
- 7b Hellstrom AK, Oskarsson H, Bordes R. J. Colloid Interface Sci. 2018; 511: 84
- 8 Wong TY, Tsai MS, Hsu LC, Lin SW, Liang PH. J. Agric. Food Chem. 2018; 66: 8124
- 9a Fu M, Chen M, Yan X, Yang X, Xiao J, Tang J. Neural Plast. 2016; 3512098
- 9b Patil KM, Naik RJ, Rajpal, Fernandes M, Ganguli M, Kumar VA. J. Am. Chem. Soc. 2012; 134: 7196
- 9c Bak A, Kozik V, Kozakiewicz D, Gajcy K, Strub DJ, Swietlicka A, Stepankova S, Imramovsky A, Polanski J, Smolinski A, Jampilek J. Int. J. Mol. Sci. 2019; 20: 1524
- 10 Hussain SA, Asilnejad B, Heesch J, Navarro M, Ji M, Shrey DW, Rajaraman RR, Sankar R. Epilepsy Res. 2020; 161: 106284
- 11a Cao J, Wang M, Yu H, She Y, Cao Z, Ye J, El-Aty AM. A, Hacimuftuoglu A, Wang J, Lao S. J. Agric. Food Chem. 2020; 68: 7298
- 11b Wei JC, Wei B, Yang W, He CW, Su HX, Wan JB, Li P, Wang YT. Food Chem. Toxicol. 2018; 119: 430
- 12a Cheng S, Sun S, Zhang H. Theor. Chem. Acc. 2017; 136: 2
- 12b Queiros L, Martins AC, Krum BN, Ke T, Aschner M, Pereira JL, Goncalves FJ. M, Milne GL, Pereira P. Toxicology 2021; 451: 152684
- 13a Du X.-J, Peng X.-J, Zhao R.-Q, Zhao W.-G, Liu X.-H, Dong W.-L. J. Mol. Struct. 2021; 1227: 129398
- 13b Qaroush AK, Assaf KI, Bardaweel SK, Al-Khateeb A. a, Alsoubani F, Al-Ramahi E, Masri M, Brück T, Troll C, Rieger B, Eftaiha A. aF. Green Chem. 2017; 19: 4305
- 14a Huang Q.-D, Ren J, Chen H, Ou W.-J, Zhang J, Fu Y, Zhu W, Yu X.-Q. ChemPlusChem 2012; 77: 584
- 14b Swale DR, Carlier PR, Hartsel JA, Ma M, Bloomquist JR. Pest Manage. Sci. 2015; 71: 1158
- 15a Jiang W, Liu Y, Ke Z, Zhang L, Zhang M, Zhou Y, Wang H, Wu C, Qiu J, Hong Q. J. Hazard. Mater. 2021; 403: 123677
- 15b Cwielag-Piasecka I, Witwicki M, Jerzykiewicz M, Jezierska J. Environ. Sci. Technol. 2017; 51: 14124
- 16 Yun MS, Chen W, Deng F, Yogo Y. Pest Manage. Sci. 2007; 63: 815
- 17a Ireni NG, Narayan R, Basak P, Raju KV. S. N. Polymer 2016; 97: 370
- 17b Gérard D, Méchin F, Saint-Loup R, Fleury E, Pascault J.-P. Prog. Org. Coat. 2022; 165: 106728
- 17c Raut SK, Behera PK, Pal TS, Mondal P, Naskar K, Singha NK. Chem. Commun. 2021; 57: 1149
- 18a Cheong JE, Zaffagni M, Chung I, Xu Y, Wang Y, Jernigan FE, Zetter BR, Sun L. Eur. J. Med. Chem. 2018; 144: 372
- 18b Wang L, Qi C, Xiong W, Jiang H. Chin. J. Catal. 2022; 43: 1598
- 18c Vranješević F, Markovic MK, Matulja D, Ambrožić G, Sordo J. Á, Laclef S, Vrček V, Marković D. Catalysts 2022; 12: 547
- 19a Maisonneuve L, Lamarzelle O, Rix E, Grau E, Cramail H. Chem. Rev. 2015; 115: 12407
- 19b Singh KN. Synth. Commun. 2007; 37: 2651
- 19c Honda M, Sonehara S, Yasuda H, Nakagawa Y, Tomishige K. Green Chem. 2011; 13: 3406
- 19d Ren L, Jiao N. Chem. Commun. 2014; 50: 3706
- 19e Sardarian AR, Inaloo ID, Zangiabadi M. New J. Chem. 2019; 43: 8557
- 20 Ion A, Doorslaer CV, Parvulescu V, Jacobs P, Vos DD. Green Chem. 2008; 10: 111
- 21 Germain N, Hermsen M, Schaub T, Trapp O. Appl. Organomet. Chem. 2017; 31: e3733
- 22 Yoshimura A, Luedtke MW, Zhdankin VV. J. Org. Chem. 2012; 77: 2087
- 23 Wang SN, Zhang GY, Shoberu A, Zou JP. J. Org. Chem. 2021; 86: 9067
- 24a Inaloo ID, Esmaeilpour M, Majnooni S, Reza OveisiA. ChemCatChem 2020; 12: 5486
- 24b Sardarian AR, Inaloo ID. RSC Adv. 2015; 5: 76626
- 24c Fan G, Luo S, Fang T, Wu Q, Song G, Li J. J. Mol. Catal. A: Chem. 2015; 404: 92
- 24d Biswas S, Khatun R, Sengupta M, Islam SM. Mol. Catal. 2018; 452: 129
- 25a Takeuchi K, Chen MY, Yuan HY, Koizumi H, Matsumoto K, Fukaya N, Choe YK, Shigeyasu S, Matsumoto S, Hamura S, Choi JC. Chem. Eur. J. 2021; 27: 18066
- 25b Ren Y, Rousseaux SA. L. J. Org. Chem. 2018; 83: 913
- 25c Schilling W, Das S. ChemSusChem 2020; 13: 6246
- 26a Ruzi R, Zhang M, Ablajan K, Zhu C. J. Org. Chem. 2017; 82: 12834
- 26b Ablajan K, Panetti GB, Yang X, Kim BS, Walsh PJ. Adv. Synth. Catal. 2017; 359: 1927
- 27 Parvatkar PT, Manetsch R, Banik BK. Chem. Asian J. 2019; 14: 6
- 28a Breugst M, von der Heiden D. Chem. Eur. J. 2018; 24: 9187
- 28b Liu D, Lei A. Chem. Asian J. 2015; 10: 806
- 28c Tian L, Zhang Q, Ablajan K. Synthesis 2022; 54: 4353
- 28d Yang K, Ke M, Lin Y, Song Q. Green Chem. 2015; 17: 1395
- 28e Sirgamalla R, Kommakula A, Banoth S, Dharavath R, Adem K, Madhu P, Boda S. ChemistrySelect 2018; 3: 1062
- 29 Wang SN, Zhang GY, Shoberu A, Zou JP. J. Org. Chem. 2021; 86: 9067
- 30 Germain N, Hermsen M, Schaub T, Trapp O. Appl. Organomet. Chem. 2017; 31: e3733
- 31 Zare H, Ghanbari MM, Jamali M, Aboodi A. Chin. Chem. Lett. 2012; 23: 883
- 32 Kianmehr E, Baghersad MH. Adv. Synth. Catal. 2011; 353: 2599