Synthesis 2020; 52(06): 796-806
DOI: 10.1055/s-0039-1690789
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Radical Nitration Using tert-Butyl Nitrite

Si-Zhe Song
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Youren Dong
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Guo-Ping Ge
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Qiang Li
b   Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, P. R. of China
,
Wen-Ting Wei
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
› Author Affiliations
This work is sponsored by the National Natural Science Foundation of China (Grant No. 21801142), the Natural Science Foundation of Zhejiang Province (No. LQ18B020002), the Natural Science Foundation of the Ningbo Municipal Natural Science Foundation (No. 2018A610412; No. 2019A610021) and the K. C. Wong Magna Fund in Ningbo University.
Further Information

Publication History

Received: 08 November 2019

Accepted after revision: 10 December 2019

Publication Date:
08 January 2020 (online)


Abstract

Nitro compounds serve as valuable intermediates for pharmaceuticals, agrochemicals, dyes, and polymers. In recent years, radical nitration using tert-butyl nitrite (t-BuONO) has attracted wide attention and desirable progress has been made. On the one hand, t-BuONO is a potential active nitro radical source and can react with various functional groups. On the other hand, as a green and novel nitration reagent, t-BuONO has relatively low price and can easily produce a radical under mild conditions, which undoubtedly provides a simple and efficient way for nitration reactions. To date, some important reviews are available that summarize the synthesis of nitro compounds. To the best of our knowledge, however, there is still no review that exclusively discusses the synthesis of nitro compounds using t-BuONO through a radical strategy. Therefore, this review aims to highlight the recent advances in radical nitration using t-BuONO as nitration reagent. The main progress in this area has been presented according to the type of reaction substrates. Special attention has been paid discussion of the reaction mechanisms and selected examples of substrates have been given. We hope this paper will be a useful reference and inspiration for those who are exploring the synthesis of nitro compounds using t-BuONO.

1 Introduction

2 Radical Nitration of Alkenes

3 Radical Nitration of Aromatics

4 Radical Nitration of Alkynes

5 Radical Nitration of 1,n-Enynes

6 Radical Nitration of Alkanes

7 Summary and Perspective

 
  • References


    • For selected reviews and papers, see:
    • 1a Formenti D, Ferretti F, Scharnagl FK, Beller M. Chem. Rev. 2019; 119: 2611
    • 1b Blaser H.-U, Steiner H, Studer M. ChemCatChem 2009; 1: 210
    • 1c Luo J, Wei W.-T. Adv. Synth. Catal. 2018; 360: 2076
    • 1d Pietrowski M. Curr. Org. Synth. 2012; 9: 470
    • 1e Bae S, Gim S, Kim H, Hanna K. Appl. Catal., B 2016; 182: 541
    • 1f Jagadeesh RV, Stemmler T, Surkus A.-E, Bauer M, Pohl M.-M, Radnik J, Junge K, Junge H, Bruckner A, Beller M. Nat. Protoc. 2015; 10: 916

      For a selected review and papers, see:
    • 2a Ballini R, Petrini M. Tetrahedron 2004; 60: 1017
    • 2b Liu J, Zhu X.-R, Ren J, Chen W.-D, Zeng B.-B. Synlett 2013; 24: 2740
    • 2c Hwu JR, Josephrajan T, Tsay S.-C. Synthesis 2006; 3305
    • 2d Ballini R, Bosica G, Fiorini D, Petrini M. Tetrahedron Lett. 2002; 43: 5233
    • 2e Taniguchi T, Yajima A, Ishibashi H. Adv. Synth. Catal. 2011; 353: 2643

      For selected papers, see:
    • 3a Fang K, Li G, She Y. J. Org. Chem. 2018; 83: 8092
    • 3b Das B, Satyalakshmi G, Suneel K, Damodar K. J. Org. Chem. 2009; 74: 8400
    • 3c Yang Y, Gao M, Deng C, Zhang D.-X, Wu L.-M, Shu W.-M, Wu A.-X. Tetrahedron 2012; 68: 6257
    • 3d Climent MJ, Corma A, Iborra S, Santos LL. Chem. Eur. J. 2009; 15: 8834
    • 3e Ran C, Yang G, Wu T, Xie M. Tetrahedron Lett. 2003; 44: 8061

      For selected papers, see:
    • 4a Aleksić M, Bertoša B, Nhili R, Uzelac L, Jarak I, Depauw S, David-Cordonnier M.-H, Kralj M, Tomić S, Karminski-Zamola G. J. Med. Chem. 2012; 55: 5044
    • 4b Thompson AM, O’Connor PD, Marshall AJ, Yardley V, Maes L, Gupta S, Launay D, Braillard S, Chatelain E, Franzblau SG, Wan B, Wang Y, Ma Z, Cooper CB, Denny WA. J. Med. Chem. 2017; 60: 4212
    • 4c Thompson AM, Bonnet M, Lee HH, Franzblau SG, Wan B, Wong GS, Cooper CB, Denny WA. ACS Med. Chem. Lett. 2017; 8: 1275

      For selected papers, see:
    • 5a Beck DE, Agama K, Marchand C, Chergui A, Pommier Y, Cushman M. J. Med. Chem. 2014; 57: 1495
    • 5b Tercel M, Lee HH, Mehta SY, Tendoung J.-JY, Bai SY, Liyanage HD. S, Pruijn FB. J. Med. Chem. 2017; 60: 5834
    • 5c Tietze LF, Major F, Schuberth I. Angew. Chem. Int. Ed. 2006; 45: 6574

      For selected papers, see:
    • 6a Oliveira AP. A, Ferreira IP, Despaigne AA. R, da Silva JG, Vieira AC. S, Santos MS, Alexandre-Moreira MS, Diniz R, Beraldo H. Acta Crystallogr., Sect. C 2019; 75: 320
    • 6b García E, Ochoa R, Vásquez I, Conesa-Milián L, Carda M, Yepes A, Vélez ID, Robledo SM, Cardona W. Med. Chem. Res. 2019; 28: 608

      For selected papers, see:
    • 7a Loesche A, Wiemann J, Rohmer M, Brandt W, Csuk R. Bioorg. Chem. 2019; 90: 103092
    • 7b Galal AM. F, Fayad W, Mettwally WS. A, Gomaa SK, Ahmed ER, El-Refai HA, Hanna AG. Med. Chem. Res. 2019; 28: 1425
    • 7c Chen Y, Wang M, Fu H, Qu X, Zhang Z, Kang F, Zhu D. Chemosphere 2019; 236: 124365

      For selected papers, see:
    • 8a Shi M, Cui S.-C. Adv. Synth. Catal. 2003; 345: 1329
    • 8b Waller FJ, Barrett AG. M, Braddock DC, Ramprasad D. Chem. Commun. 1997; 613
    • 8c García C, Melguizo M, Cobo J, Sánchez A, Nogueras M, López MD. Synlett 2001; 57
    • 8d Waller FJ, Barrett AG. M, Braddock DC, Ramprasad D, McKinnell RM, White AJ. P, Williams DJ, Ducray R. J. Org. Chem. 1999; 64: 2910

      For selected reviews and papers, see:
    • 9a Vogler T, Studer A. Synthesis 2008; 1979
    • 9b Tebben L, Studer A. Angew. Chem. Int. Ed. 2011; 50: 5034
    • 9c Hwu JR, Chen K.-L, Ananthan S, Patel HV. Organometallics 1996; 15: 499
    • 9d Maity S, Manna S, Rana S, Naveen T, Mallick A, Maiti D. J. Am. Chem. Soc. 2013; 135: 3355
    • 9e Taniguchi T, Fujii T, Ishibashi H. J. Org. Chem. 2010; 75: 8126
    • 9f Grenier J.-L, Catteau J.-P, Cotelle P. Synth. Commun. 1999; 29: 1201
    • 9g Manna S, Maity S, Rana S, Agasti S, Maiti D. Org. Lett. 2012; 14: 1736
    • 9h Hoover JM, Stahl SS. J. Am. Chem. Soc. 2011; 133: 16901
    • 9i Jiang M, Yang H, Li Y, Jia Z, Fu H. RSC Adv. 2013; 3: 25602
    • 9j Zhu X, Qiao L, Ye P, Ying B, Xu J, Shen C, Zhang P. RSC Adv. 2016; 6: 89979
    • 9k Siri O, Jaquinod L, Smith KM. Tetrahedron Lett. 2000; 41: 3583
    • 9l Tanaka M, Muro E, Ando H, Xu Q, Fujiwara M, Souma Y, Yamaguchi Y. J. Org. Chem. 2000; 65: 2972
    • 9m Eiichiro H, Tohru Y, Teruaki M. Bull. Chem. Soc. Jpn. 1995; 68: 3629

      For selected reviews and papers, see:
    • 10a Khaligh NG. Curr. Org. Chem. 2018; 22: 1120
    • 10b Wei W.-T, Zhu W.-M, Wu Y, Huang Y.-L, Liang H. Chin. J. Org. Chem. 2017; 37: 1916
    • 10c Zhang T.-S, Wang R, Cai P.-J, Hao W.-J, Tu S.-J, Jiang B. Org. Chem. Front. 2019; 6: 2968
    • 10d Dutta U, Maity S, Kancherla R, Maiti D. Org. Lett. 2014; 16: 6302

      For selected reviews, see:
    • 11a Song L.-R, Fan Z, Zhang A. Org. Biomol. Chem. 2019; 17: 1351
    • 11b Ballini R, Araújo N, Gil MV, Román E, Serrano JA. Chem. Rev. 2013; 113: 3493
    • 11c Yan G, Borah AJ, Wang L. Org. Biomol. Chem. 2014; 12: 6049
  • 12 For a selected paper, see: Park D.-Y, Lee K.-Y, Gowrisankar S, Kim J. Bull. Korean Chem. Soc. 2008; 29: 701

    • For recent selected papers see
    • 13a Fu Y.-X, Hu S.-S, Li S.-Y, Li X.-J. Synth. Commun. 2019; 49: 1067
    • 13b Gildner PG, Gietter AA. S, Cui D, Watson DA. J. Am. Chem. Soc. 2012; 134: 9942
  • 14 Cao Q, Liu J, Yu L, Gui QW, Chen X, Tan Z. Synth. Commun. 2015; 45: 2181
  • 15 Chumnanvej N, Katrun P, Pohmakotr M, Reutrakul V, Soorukram D, Kuhakarn C. Chin. J. Chem. 2016; 34: 830
  • 16 Taniguchi T, Sugiura Y, Hatta T, Yajima A, Ishibashi H. Chem. Commun. 2013; 49: 2198
  • 17 Maity S, Naveen T, Sharma U, Maiti D. Org. Lett. 2013; 15: 3384
  • 18 Manna S, Jana S, Saboo T, Maji A, Maiti D. Chem. Commun. 2013; 49: 5286

    • For selected papers, see:
    • 19a Nakazaki A, Mori A, Kobayashi S, Nishikawa T. Chem. Asian J. 2016; 11: 3267
    • 19b Cui B.-D, You Y, Zhao J.-Q, Zuo J, Wu Z.-J, Xu X.-Y, Zhang X.-M, Yuan W.-C. Chem. Commun. 2015; 51: 757
  • 20 Shen T, Yuan Y, Jiao N. Chem. Commun. 2013; 50: 554
  • 21 Gao L.-H, Meng X.-X, Wang Y.-N, Song S.-Z, Ge G.-P, Dong Y, Wei W.-T, Liu Y.-Y, Li Q. Asian J. Org. Chem. 2019; 8: 348

    • For a selected review and papers, see:
    • 22a Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540
    • 22b Pande MA, Samant SD. Synth. Commun. 2010; 40: 3734
    • 22c Nowrouzi N, Mehranpour AM, Bashiri E, Shayan Z. Tetrahedron Lett. 2012; 53: 4841
    • 22d Cho JK, Kim Y.-T, Kim YG, Lee Y.-S, Sung S.-Y, Chung K.-H, Lee B.-S. Res. Chem. Intermed. 2006; 32: 759

      For a selected book and papers, see:
    • 23a Weissermel K, Arpe H.-J. Industrial Organic Chemistry, 4th ed. Wiley-VCH; Weinheim: 2003
    • 23b Sun H.-B, Hua R, Yin Y. J. Org. Chem. 2005; 70: 9071
    • 23c Fors BP, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 12898
  • 24 Wu X.-F, Schranck J, Neumann H, Beller M. Chem. Commun. 2011; 47: 12462
  • 25 Kilpatrick B, Heller M, Arns S. Chem. Commun. 2013; 49: 514

    • For a selected review and paper, see:
    • 26a Papagiannouli I, Iliopoulos K, Gindre D, Sahraoui B, Krupka O, Smokal V, Kolendo A, Couris S. Chem. Phys. Lett. 2012; 554: 107
    • 26b Bafana A, Devi SS, Chakrabarti T. Environ. Rev. 2011; 19: 350
  • 27 Majhi B, Kundu D, Ahammed S, Ranu BC. Chem. Eur. J. 2014; 20: 9862
  • 28 Zhao J, Li P, Xia C, Li F. RSC Adv. 2015; 5: 32835
  • 29 Liang Y.-F, Li X, Wang X, Yan Y, Feng P, Jiao N. ACS Catal. 2015; 5: 1956

    • For selected reviews see:
    • 30a Arancon RA. D, Lin CS. K, Vargasc C, Luque R. Org. Biomol. Chem. 2014; 12: 10
    • 30b Xu F, Han W. Chin. J. Org. Chem. 2018; 38: 2519
    • 30c Jin F, Han W. Chem. Commun. 2015; 51: 9133
  • 31 For a selected paper, see: Han W, Chen J, Jin F, Yuan X. Synlett 2018; 29: 369
  • 32 Wei W.-T, Zhu W.-M, Liang W, Wu Y, Huang H.-Y, Huang Y.-L, Luo J, Liang H. Synlett 2017; 28: 2153
  • 33 Yan H, Mao J, Rong G, Liu D, Zheng Y, He Y. Green Chem. 2015; 17: 2723

    • For selected papers, see:
    • 34a Luo J, Wu B, Chen M.-W, Jiang G.-F, Zhou Y.-G. Org. Lett. 2014; 16: 2578
    • 34b Companyó X, Zea A, Alba A.-NR, Mazzanti A, Moyano A, Rios R. Chem. Commun. 2010; 46: 6953
    • 34c D’yachenko E, Glukhareva T, Dyudya L, Eltsov O, Morzherin Y. Molecules 2005; 10: 1101
  • 35 Yang X.-H, Ouyang X.-H, Wei W.-T, Song R.-J, Li J.-H. Adv. Synth. Catal. 2015; 357: 1161
  • 36 Lin Y, Kong W, Song Q. Org. Lett. 2016; 18: 3702

    • For selected reviews, see:
    • 37a Jones AC, May JA, Sarpong R, Stoltz BM. Angew. Chem. Int. Ed. 2014; 53: 2556
    • 37b Wille U. Chem. Rev. 2013; 113: 813
  • 38 Liu Y, Zhang J.-L, Song R.-J, Qian P.-C, Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 9017
  • 39 Hu M, Liu B, Ouyang X.-H, Song R.-J, Li J.-H. Adv. Synth. Catal. 2015; 357: 3332

    • For selected papers, see:
    • 40a Ryu I, Miyazato H, Kuriyama H, Matsu K, Tojino M, Fukuyama T, Minakata S, Komatsu M. J. Am. Chem. Soc. 2003; 125: 5632
    • 40b Ko HM, Lee CW, Kwon HK, Chung HS, Choi SY, Chung YK, Lee E. Angew. Chem. Int. Ed. 2009; 48: 2364
    • 40c Mondal S, Mohamed RK, Manoharan M, Phan H, Alabugin IV. Org. Lett. 2013; 15: 5650
    • 40d Miyabe H, Asada R, Toyoda A, Takemoto Y. Angew. Chem. Int. Ed. 2006; 45: 5863
  • 41 Hao X.-H, Gao P, Song X.-R, Qiu Y.-F, Jin D.-P, Liu X.-Y, Liang Y.-M. Chem. Commun. 2015; 51: 6839
  • 42 Wei W.-T, Ying W.-W, Bao W.-H, Gao L.-H, Xu X.-D, Wang Y.-N, Meng X.-X, Chen G.-P, Li Q. ACS Sustainable Chem. Eng. 2018; 6: 15301

    • For selected papers, see:
    • 43a Yamaguchi K, Shinachi S, Mizuno N. Chem. Commun. 2004; 424
    • 43b Isozaki S, Nishiwaki Y, Sakaguchia S, Ishii Y. Chem. Commun. 2001; 1352
  • 44 Deng G.-B, Zhang J.-L, Liu Y.-Y, Liu B, Yang X.-H, Li J.-H. Chem. Commun. 2015; 51: 1886
  • 45 Zhang W, Ren S, Zhang J, Liu Y. J. Org. Chem. 2015; 80: 5973
  • 46 Wei W.-T, Zhu W.-M, Ying W.-W, Wang Y.-N, Bao W.-H, Gao L.-H, Luo Y.-J, Liang H. Adv. Synth. Catal. 2017; 359: 3551