Denitrative functionalization of nitroarenes
Tóm tắt
Denitrative functionalization of nitroaromatic compounds has become a very intriguing challenge in synthetic chemistry. Herein, various methodologies for
$${\text{C}}_{{sp^{2} }}$$
–NO2 bond cleavage of nitroaromatic compounds have been reviewed. We survey the literature for the reactions in which nitroarenes have been used as the electrophilic coupling partners for the formation of
$${\text{C}}_{{sp^{2} }}$$
–O,
$${\text{C}}_{{sp^{2} }}$$
–S,
$${\text{C}}_{{sp^{2} }}$$
–N,
$${\text{C}}_{{sp^{2} }}$$
–H and
$${\text{C}}_{{sp^{2} }}$$
–C bonds via transition metal-catalyzed cross-coupling reactions. A brief discussion about the mechanism of the reactions has also been presented.
Tài liệu tham khảo
M. Rauser, C. Ascheberg, M. Niggemann, Angew. Chem. Int. Ed. 56, 11570 (2017)
F. Al Momani, J. Photochem. Photobio. A. Chem. 179, 184 (2006)
K. Chen, W. Chen, X. Yi, W. Chen, M. Liu, H. Wu, Chem. Commum. 55, 9287 (2019)
M. Mondal, S.K. Bharadwaj, U. Bora, New J. Chem. 39, 31 (2015)
R. Friemann, M.M. Ivkovic-Jensen, D.J. Lessner, C.-L. Yu, D.T. Gibson, R.E. Parales, H. Eklund, S. Ramaswamy, J. Mol. Biol. 348, 1139 (2005)
K.K. Krishnan, S.M. Ujwaldev, K.S. Sindhu, G. Anilkumar, Tetrahedron 72, 7393 (2016)
L. Peng, Z. Hu, Z. Tang, Y. Jiao, X. Xu, Chin. Chem. Lett. 30, 1481 (2019)
Y. Yang, Angew. Chem. Int. Ed. 56, 15802 (2017)
L. Rocard, P. Hudhomme, Catalysts 9, 213 (2019)
X.H. Cai, H. Zhang, H. Guo, Curr. Org. Chem. 23, 1131 (2019)
K. Muto, T. Okita, J. Yamaguchi, ACS Catal. 10, 9856 (2020)
F.J. Williams, P.E. Donahue, J. Org. Chem. 42, 3414 (1977)
H. Sun, S.G. DiMagno, Angew. Chem. Int. Ed. 45, 2720 (2006)
X.C. Yu, B. Li, B.H. Yu, Q. Xu, Chin. Chem. Lett. 24, 605 (2013)
M. Xuan, C. Lu, B.L. Lin, Chin. Chem. Lett. 31, 48 (2019)
R. Ghosh, E. Lindstedt, N. Jalalian, B. Olofsson, Chem. Open 3, 54 (2014)
H. Zhang, D. Ma, W. Cao, Synlett 2, 243 (2007)
W. Reinders, W.E. Ringer, Red. Trav. Chim. Pays-Bas 18, 326 (1899)
N. Kornblum, L. Cheng, R.C. Kerber, M.M. Kestner, B.N. Newton, H.W. Pinnick, R.G. Smith, P.A. Wade, J. Org. Chem. 41, 1560 (1976)
F. Zamiran, A. Ghaderi, J. Iran. Chem. Soc. 16, 293 (2019)
R. Soltani. F. Abdollahi, A. Ghaderi, J. Chem. Res. (2020). (in Press)
H. Zheng, Q. Zhang, J. Chen, M. Liu, S. Cheng, J. Ding, H. Wu, W. Su, J. Org. Chem. 74, 943 (2009)
C. Qin, J. Chen, H. Wu, J. Cheng, Q. Zhang, B. Zuo, W. Su, J. Ding, Tetrahedron Lett. 49, 1884 (2008)
C. Qin, H. Wu, J. Cheng, X.A. Chen, M. Liu, W. Zhang, W. Su, J. Ding, J. Org. Chem. 72, 4102 (2007)
X. Zheng, J. Ding, J. Chen, W. Gao, M. Liu, H. Wu, Org. Lett. 13, 1726 (2011)
J. Zhang, J. Chen, M. Liu, X. Zheng, J. Ding, H. Wu, Green Chem. 14, 912 (2012)
D. Peng, A. Yu, H. Wang, Y. Wu, J. Chang, Tetrahedron 69, 6884 (2013)
J. Chen, X. Wang, X. Zheng, J. Ding, M. Liu, H. Wu, Tetrahedron 68, 8905 (2012)
H. Wang, A. Yu, A. Cao, J. Chang, Y. Wu, Appl. Organomet. Chem. 27, 611 (2013)
N.T. Phan, T.T. Nguyen, V.T. Nguyen, K.D. Nguyen, ChemCatChem. 5, 2374 (2013)
A.P. Sarkate, S.S. Bahekar, V.M. Wadhai, G.N. Ghandge, P.S. Wakte, D.B. Shinde, Synlett 24, 1513 (2013)
T. Maity, D. Saha, S. Bhunia, P. Brandao, S. Das, S. Koner, RSC Adv. 5, 82179 (2015)
T. Maity, S. Bhunia, S. Das, S. Koner, RSC Adv. 6, 33380 (2016)
P. Leo, G. Orcajo, D. Briones, G. Calleja, M. Sánchez-Sánchez, F. Martínez, Nanomaterials 7, 149 (2017)
T. Begum, M. Mondal, M.P. Borpuzari, R. Kar, P.K. Gogoi, U. Bora, Eur. J. Org. Chem. 2017, 3244 (2017)
S.S. Bahekar, A.P. Sarkate, V.M. Wadhai, P.S. Wakte, D.B. Shinde, Catal. Commun. 41, 123 (2013)
H. Tian, A. Cao, L. Qiao, A. Yu, J. Chang, Y. Wu, Tetrahedron 70, 9107 (2014)
A. Rostami, A. Rostami, A. Ghaderi, J. Org. Chem. 80, 8694 (2015)
F.M. Moghaddam, R. Pourkaveh, Catal. Commun. 94, 33 (2017)
S. Farzin, A. Rahimi, K. Amiri, A. Rostami, A. Rostami, Appl. Organomet. Chem. 32, 4409 (2018)
M.R. Yadav, M. Nagaoka, M. Kashihara, R.L. Zhong, T. Miyazaki, S. Sakaki, Y. Nakao, J. Am. Chem. Soc. 139, 9423 (2017)
K.K. Asahara, T. Okita, A.N. Saito, K. Muto, Y. Nakao, J. Yamaguchi, Org. Lett. 21, 4721 (2019)
M. Kashihara, R.L. Zhong, K. Semba, S. Sakaki, Y. Nakao, Chem. Commun. 55, 9291 (2019)
B. Feng, Y. Yang, J. You, Chem. Commun. 56, 790 (2020)
T. Okita, K.K. Asahara, K. Muto, J. Yamaguchi, Org. Lett. 22, 3205 (2020)
F. Inoue, M. Kashihara, M.R. Yadav, Y. Nakao, Angew. Chem. Int. Ed. 56, 13307 (2017)
W. Chen, K. Chen, W. Chen, M. Liu, H. Wu, ACS Catal. 9, 8110 (2019)
C.W. Rees, S.C. Tsoi, Chem. Commun. 5, 415 (2000)
T.C. Fessard, H. Motoyoshi, E.M. Carreira, Angew. Chem. Int. Ed. 46, 2078 (2007)
M. Kashihara, M.R. Yadav, Y. Nakao, Org. Lett. 20, 1655 (2018)