Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Qi Zhang; Kaki Raveendra Babu; Zhouliang Huang; Jinna Song; Xihe Bi

doi:10.1055/s-0037-1610038

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(15): 2891-2896
DOI: 10.1055/s-0037-1610038

special topic

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Authors

Qi Zhang

^aDepartment of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China eMail: bixh507@nenu.edu.cn
Kaki Raveendra Babu

^aDepartment of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China eMail: bixh507@nenu.edu.cn
Zhouliang Huang

^bCollege of Life Sciences, Jilin University, 2699 Qianjin Street, 130012 Changchun, P. R. of China
Jinna Song*

^bCollege of Life Sciences, Jilin University, 2699 Qianjin Street, 130012 Changchun, P. R. of China
Xihe Bi *

^aDepartment of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China eMail: bixh507@nenu.edu.cn

^cState Key Laboratory of Elemento-Organic Chemistry, Nankai University, 94 Weijin Road, 300071 Tianjin, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate trihydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

Key words

polynitrophenols - visible light - arylboronic acid - nitration - copper

Volltext

Referenzen

References

1a Ciamician G. Science 1912; 36: 385
1b Yoon TP. Ischay MA. Du J. Nat. Chem. 2010; 2: 527
1c Ravelli D. Dondi D. Fagnoni M. Albini A. Chem. Soc. Rev. 2009; 38: 1999
1d Gust D. Moore TA. Moore AL. Acc. Chem. Res. 1993; 26: 198

2 Narayanam JM. R. Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102

3a Prier CK. Rankic DA. MacMillan DW. C. Chem. Rev. 2013; 113: 5322
3b Hopkinson MN. Sahoo B. Li JL. Glorius F. Chem. Eur. J. 2014; 20: 3874
3c Shaw MH. Twilton J. MacMillan DW. C. J. Org. Chem. 2016; 81: 6898

4a Noble A. MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 11602
4b Terrett JA. Clift MD. MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 6858
4c Pirnot MT. Rankic DA. Martin DB. C. MacMillan DW. C. Science 2013; 339: 1593
4d Nagib DA. Scott ME. MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 10875
4e Nicewicz DA. MacMillan DW. C. Science 2008; 322: 77

5a Du J. Yoon TP. J. Am. Chem. Soc. 2009; 131: 14604
5b Ischay MA. Anzovino ME. Du J. Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886

6a Konieczynska MD. Dai C. Stephenson CR. J. Org. Biomol. Chem. 2012; 10: 4509
6b Dai C. Narayanam JM. R. Stephenson CR. J. Nat. Chem. 2011; 3: 140
6c Condie AG. González-Gómez JC. Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464
6d Tucker JW. Narayanam JM. R. Krabbe SW. Stephenson CR. J. Org. Lett. 2010; 12: 368
6e Narayanam JM. R. Tucker JW. Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756

7a Booth G. Nitro Compounds, Aromatic. In Ullmann’s Encyclopedia of Industial Chemistry. Wiley-VCH; Weinheim: 2000
7b Heaney F. Synthesis 2001; 2528
7c Schlosser M. Ruzziconi R. Synthesis 2010; 2111
7d Schofield K. Aromatic Nitration . Cambridge University Press; Cambridge: 1980
7e Chu W. Zhou D. Gaba V. Liu J. Li S. Peng X. Xu J. Dhavale D. Bagchi DP. d’Avignon A. Shakerdge NB. Bacskai BJ. Tu Z. Kotzbauer PT. Mach RH. J. Med. Chem. 2015; 58: 6002
7f Ikeda S. Toganoh M. Easwaramoorthi S. Lim JM. Kim D. Furuta H. J. Org. Chem. 2010; 75: 8637

8a Esakkidurai T. Kumarraja M. Pitchumani K. J. Chem. Sci. 2003; 115: 113
8b Olah GA. Malhotra R. Narang SC. Nitration: Methods and Mechanisms . Wiley-VCH; Weinheim: 1989
8c Crampton MR. Cropper EL. Gibbons LM. Millar RW. Green Chem. 2002; 4: 275

9a Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002; 102: 1359
9b Thiebes C. Prakash GK. S. Petasis NA. Olah GA. Synlett 1998; 141
9c Prakash GK. S. Chacko S. Panja C. Thomas TE. Gurung L. Rasul G. Mathew T. Olah GA. Adv. Synth. Catal. 2009; 351: 1567

10a Fan Z. Ni J. Zhang A. J. Am. Chem. Soc. 2016; 138: 8470
10b Prakash GK. S. Panja C. Mathew T. Surampudi V. Petasis NA. Olah GA. Org. Lett. 2004; 6: 2205
10c Manna S. Maity S. Rana S. Agasti S. Maiti D. Org. Lett. 2012; 14: 1736
10d Bose A. Mal P. Chem. Commun. 2017; 53: 11368

11 Sun H.-B. Hua R. Yin Y. J. Org. Chem. 2005; 70: 9071
12 Natarajan P. Chaudhary R. Venugopalan P. J. Org. Chem. 2015; 80: 10498
13 Dove MF. A. Manz B. Montgomery J. Pattenden G. Wood SA. J. Chem. Soc., Perkin Trans. 1 1998; 1589
14 Rajagopal R. Srinivasan KV. Synth. Commun. 2003; 33: 961
15 Zolfigol MA. Ghaemi E. Madrakian E. Synth. Commun. 2000; 30: 1689

16a Zolfigol MA. Ghaemi E. Madrakian E. Molecules 2001; 6: 614
16b Zolfigol MA. Ghaemi E. Madrakian E. Synlett 2003; 191
16c Zolfigol MA. Madrakian E. Ghaemi E. Molecules 2002; 7: 734

17 Shackelford SA. Anderson MB. Christie LC. Goetzen T. Guzman MC. Hananel MA. Kornreich WD. Li H. Pathak VP. Rabinovich AK. Rajapakse RJ. Truesdale LK. Tsank SM. Vazir HN. J. Org. Chem. 2003; 68: 267
18 Toyao T. Ueno N. Miyahara K. Matsui Y. Kim T.-H. Horiuchi Y. Ikeda H. Matsuoka M. Chem. Commun. 2015; 51: 16103

Zusatzmaterial

Supporting Information (PDF)