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Synthesis 2018; 50(04): 711-722
DOI: 10.1055/s-0036-1589155
DOI: 10.1055/s-0036-1589155
short review
tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis
We thank the Natural Science Foundation of China (NSFC, No. 21362030 and 21562038) for supporting our research.Weitere Informationen
Publikationsverlauf
Received: 27. Oktober 2017
Accepted after revision: 22. November 2017
Publikationsdatum:
14. Dezember 2017 (online)
Abstract
tert-Butyl nitrite (TBN) is an important metal-free reagent that is widely applied in various organic transformations. Besides its traditional applications in nitrosation and diazotization, its ability to activate molecular oxygen to enable the initiation of radical reactions, including nitration, oximation, oxidation, and so on, has attracted extensively attention in the past decade. This review highlights recent advances in this field to promote further exploration of this versatile compound.
1 Introduction
2 Reactions Involving TBN
2.1 Nitrosation
2.2 Oximation
2.3 Diazotization
2.4 Nitration
2.5 Oxidation
2.6 Other Reactions
3 Conclusion and Perspective
-
References
- 1a Hartung WH. Munch JC. J. Am. Chem. Soc. 1929; 51: 2262
- 1b Pradhan BP. De S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1982; 21: 823
- 2a Dai J.-J. Fang C. Xiao B. Yi J. Xu J. Liu Z.-J. Lu X. Liu L. Fu Y. J. Am. Chem. Soc. 2013; 135: 8436
- 2b Wang X. Xu Y. Mo F.-Y. Jin G.-J. Qiu D. Feng J.-J. Ye Y.-X. Zhang S.-G. Zhang Y. Wang J.-B. J. Am. Chem. Soc. 2013; 135: 10330
- 2c Danoun G. Bayarmagnai B. Grünberg M.-F. Gooßen L.-J. Angew. Chem. Int. Ed. 2013; 52: 7972
- 2d Qiu D. Meng H. Jin L. Wang S. Tang S.-G. Wang X. Mo F.-Y. Zhang Y. Wang J.-B. Angew. Chem. Int. Ed. 2013; 52: 11581
- 2e Crisóstomo F.-P. Martín T. Carrillo R. Angew. Chem. Int. Ed. 2014; 53: 2181
- 2f Akama T. Baker S.-J. Zhang Y.-K. Hernandez V. Zhou H. Sanders V. Freund Y. Kimura R. Maples K.-R. Plattner J.-J. Bioorg. Med. Chem. Lett. 2009; 19: 2129
- 2g Piccionello A.-P. Pace A. Pierro P. Pibiri I. Buscemi S. Vivona N. Tetrahedron 2009; 65: 119
- 2h Ahmed-Omer B. Barrow D.-A. Wirth T. Tetrahedron Lett. 2009; 50: 3352
- 2i Chakraborty A. Jana S. Kibriya G. Dey A. Hajra A. RSC Adv. 2016; 6: 34146
- 3a Koley D. Colón O.-C. Savinov S.-N. Org. Lett. 2009; 11: 4172
- 3b Wu X.-F. Schranck J. Neumann H. Beller M. Chem. Commun. 2011; 47: 12462
- 3c Kilpatrick B. Heller M. Arns S. Chem. Commun. 2013; 49: 514
- 3d Taniguchi T. Yajima A. Ishibashi H. Adv. Synth. Catal. 2011; 353: 2643
- 3e Taniguchi T. Sugiura Y. Hatta T. Yajima A. Ishibashi H. Chem. Commun. 2013; 49: 2198
- 4a Barton DH. R. Beaton JM. Geller LE. Pechet MM. J. Am. Chem. Soc. 1960; 82: 2640
- 4b Barton DH. R. Beaton JM. Geller LE. Pechet MM. J. Am. Chem. Soc. 1961; 83: 4076
- 5a Liu Y. Zhang J.-L. Song R.-J. Qian P.-C. Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 9017
- 5b Shen T. Yuan Y.-Z. Jiao N. Chem. Commun. 2014; 50: 554
- 5c Sau P. Santra SK. Rakshit A. Patel BK. J. Org. Chem. 2017; 82: 6358
- 6a Dutta U. Maity S. Kancherla R. Maiti D. Org. Lett. 2014; 16: 6302
- 6b Yan H. Rong G.-G. Liu D. Zheng Y. Chen J. Mao J.-C. Org. Lett. 2014; 16: 6306
- 6c Yan H. Mao J.-C. Rong G.-G. Liu D.-F. Zheng Y. He Y. Green Chem. 2015; 17: 2723
- 6d Yang X.-H. Ouyang X.-H. Wei W.-T. Song R.-J. Li J.-H. Adv. Synth. Catal. 2015; 357: 1161
- 6e 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
- 7a Gowenlock BG. Richter-Addo GB. Chem. Rev. 2004; 104: 3315
- 7b Culotta E. Koshland DE. Jr. Science (Washington, D. C.) 1992; 258: 1862
- 7c Rival Y. Grassy G. Michel G. Chem. Pharm. Bull. 1992; 40: 1170
- 7d Teulade JC. Grassy G. Girard JP. Chapat JP. de Simeon de Buochberg M. Eur. J. Med. Chem. 1978; 13: 271
- 7e Bouhrira K. Ouahiba F. Zerouali D. Hammouti B. Zertoubi M. Benchat N. E-J. Chem. 2010; 7: S35; http://www.hindawi.com/journals/jchem/
- 8a Loeppky RN. Outram JR. N-Nitroso Compounds: Occurrence and Biological Effects . IARC Scientific Publishers; Lyon: 1982
- 8b Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry, ACS Symposium Series No. 553. Loeppky RN. Michejda CJ. American Chemical Society; Washington DC: 1994
- 9a Wang PG. Cai TB. Taniguchi N. Nitric Oxide Donor, For Pharmaceutical and Biological Applications . Wiley-VCH; Weinheim: 2005
- 9b Wang PG. Xian M. Tang X. Wu X. Wen Z. Cai T. Janczuk AJ. Chem. Rev. 2002; 102: 1091
- 10a N-Nitrosamines, ACS Symposium Series No. 101. Anselme J.-P. American Chemical Society; Washington DC: 1979
- 10b Zolfigol MA. Shirini F. Choghamarani AG. Taqian-Nasab A. Keypour H. Salehzadeh S. J. Chem. Res., Synop. 2000; 420
- 10c Olah G. Noszkwo L. Kuhn S. Szelke M. Chem. Ber. 1956; 89: 2374
- 10d Zolfigol MA. Zebarjadian MH. Chehardoli G. Keypour H. Salehzadeh S. Shamsipur M. J. Org. Chem. 2001; 66: 3619
- 10e Castedo L. Riguera R. Vazquez MP. J. Chem. Soc., Chem. Commun. 1983; 301
- 10f White EH. J. Am. Chem. Soc. 1955; 77: 6008
- 10g Challis BC. Kyrtopoulos SA. J. Chem. Soc., Perkin Trans. 1 1979; 299
- 11a Chaudhary P. Gupta S. Muniyappan N. Sabiah S. Kandasamy J. Green Chem. 2016; 18: 2323
- 11b Yedage S.-L. Bhanage B.-M. J. Org. Chem. 2017; 82: 5769
- 11c Monir K. Ghosh M. Jana S. Mondal P. Majee A. Hajra A. Org. Biomol. Chem. 2015; 13: 8717
- 12a Prateeptongkum S. Jovel I. Jackstell R. Vogl N. Weckbeckerb C. Beller M. Chem. Commun. 2009; 1990
- 12b Gao X. Zhang F. Deng G.-J. Yang L. Org. Lett. 2014; 16: 3364
- 12c Peng X.-X. Deng Y.-J. Yang X.-L. Zhang L. Yu W. Han B. Org. Lett. 2014; 16: 4650
- 12d Zhang X.-W. Xiao Z.-F. Zhuang Y.-J. Wang M.-M. Kang Y.-B. Adv. Synth. Catal. 2016; 358: 1942
- 12e Chen F. Zhou N.-N. Zhan J.-L. Han B. Yu W. Org. Chem. Front. 2017; 4: 135
- 13 Liang Y.-F. Li X.-Y. Wang X.-Y. Yan Y.-P. Feng P. Jiao N. ACS Catal. 2015; 5: 1956
- 14a Hamasaki A. Kuwada H. Tokunaga M. Tetrahedron Lett. 2012; 53: 811
- 14b Shen Z.-L. Chen M. Fang T.-T. Li M.-C. Mo W.-M. Hu B.-X. Sun N. Hu X.-Q. Tetrahedron Lett. 2015; 56: 2768
- 14c He X. Shen Z. Mo W. Sun N. Hu B. Hu X. Adv. Synth. Catal. 2009; 351: 89
- 14d Li L.-C. Matsuda R. Tanaka I. Sato H. Kanoo P. Jeon H.-J. Foo M.-L. Wakamiya A. Murata Y. Kitagawa S. J. Am. Chem. Soc. 2014; 136: 7543
- 14e Xie Y. Mo W.-M. Xu D. Shen Z.-L. Sun N. Hu B.-X. Hu X.-Q. J. Org. Chem. 2007; 72: 4288
- 14f Holan M. Jahn U. Org. Lett. 2014; 16: 58
- 14g Ohkubo K. Fujimoto A. Fukuzumi S. J. Am. Chem. Soc. 2013; 135: 5368
- 14h Zhang H. Wang G.-B. Tetrahedron Lett. 2014; 55: 56
- 14i Huang H.-L. Cheng K. Yao B.-B. Xie Y.-J. Zhang Y.-H. J. Org. Chem. 2011; 76: 5732
- 15a Shu Z.-B. Ye Y.-X. Deng Y.-F. Zhang Y. Wang J.-B. Angew. Chem. Int. Ed. 2013; 52: 10573
- 15b Dutta U. Lupton DW. Maiti D. Org. Lett. 2016; 18: 860
- 16 Hu M. Song R.-J. Li J.-H. Angew. Chem. Int. Ed. 2015; 54: 608
- 17 Barral K. Moorhouse AD. Moses JE. Org. Lett. 2007; 9: 1809
- 18 Shen Z. Sheng L. Zhang X. Mo W. Hua B. Sun N. Hu X. Tetrahedron Lett. 2013; 54: 1579