Organic Letters
Letter
M.; Chatani, N.; Tobisu, M. Synlett 2017, 28, 2569. (d) Haibach, M.
C.; Stoltz, B. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2017, 56, 15123.
(14) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
(15) An analogous reaction can be found in the literature: Muth, C.
W.; Yang, K. E. J. Heterocycl. Chem. 1996, 33, 249.
(16) See Figure S11 for unsuccessful nitroarene substrates.
(17) Wu, X.; Fors, B. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011,
50, 9943.
REFERENCES
■
(1) (a) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods
and Mechanism; Wiley-VCH: New York, 2001. (b) Schofiled, K.
Aromatic Nitrations; Cambridge University Press: Cambridge, 1980.
(c) Gu, S. X.; Jing, H. W.; Liang, Y. M. Synth. Commun. 1997, 27,
2793. (d) Suzuki, H.; Murashima, T.; Mori, J. J. Chem. Soc., Chem.
Commun. 1994, 1443. (e) Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc.
2009, 131, 12898. (f) Lu, Y.; Li, Y.; Zhang, R.; Jin, K.; Duan, C.
Tetrahedron 2013, 69, 9422. (g) Fan, Z.; Ni, J.; Zhang, A. J. Am. Chem.
Soc. 2016, 138, 8470.
(2) (a) Lamson, D. W.; Ulrich, P.; Hutchins, R. O. J. Org. Chem.
1973, 38, 2928. (b) Fielden, R.; Meth-Cohn, O.; Suschitzky, H. J.
Chem. Soc., Perkin Trans. 1 1973, 1, 696. (c) Giumanini, A. G.;
Verardo, G. Can. J. Chem. 1997, 75, 469. (d) Rees, C. W.; Tsoi, S. C.
Chem. Commun. 2000, 415.
(3) (a) Larock, R. C. Comprehensive Organic Transformations; Wiley-
VCH: New York, 1989. (b) Sandler, S. R.; Karo, W. Organic Functional
Group Preparation; Academic Press: New York, 1968. (c) Yoon, N. M.;
Choi, J. Synlett 1993, 135. (d) Barboni, L.; Bartoli, G.; Marcantoni, E.;
Pertrini, M. J. Chem. Soc., Perkin Trans. 1 1990, 1, 2133. (e) Stromnova,
T. A.; Orlova, S. T. Russ. Chem. Bull. 2002, 51, 2286. (f) Liu, X.; Li, H.-
Q.; Ye, S.; Liu, Y.-M.; He, H.-Y.; Cao, Y. Angew. Chem., Int. Ed. 2014,
53, 7624.
(4) For reductive denitration of nitroalkanes, see: (a) Ono, N.; Kaji,
A. Synthesis 1986, 693. (b) Weis, C. D.; Newkome, G. R. Synthesis
1995, 1053. (c) Fessard, T. C.; Motoyoshi, H.; Carreira, E. M. Angew.
Chem., Int. Ed. 2007, 46, 2078.
(5) Kornblum, N. Organic Reactions; Wiley: New York, 1944; Vol. 2,
p 262, Chapter 7.
(6) (a) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH:
New York, 2001. (b) Booth, G. Nitro Compounds, Aromatic; Ullmann’s
Encyclopedia of Industrial Chemistry; Wiley-VCH: New York, 2012.
(7) Mąkosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20, 282.
(8) (a) Caron, L.; Campeau, L.-C.; Fagnou, K. Org. Lett. 2008, 10,
4533. (b) Guo, P.; Joo, J. M.; Rakshit, S.; Sames, D. J. Am. Chem. Soc.
2011, 133, 16338. (c) Iaroshenko, V. O.; Gevorgyan, A.; Davydova,
O.; Villinger, A.; Langer, P. J. Org. Chem. 2014, 79, 2906.
(d) Iaroshenko, V. O.; Gevorgyan, A.; Mkrtchyan, S.; Grigoryan, T.;
Movsisyan, E.; Villinger, A.; Langer, P. ChemCatChem 2015, 7, 316.
(e) Yi, Z.; Aschenaki, Y.; Daley, R.; Davick, S.; Schnaith, A.; Wander,
R.; Kalyani, D. J. Org. Chem. 2017, 82, 6946.
(9) (a) Yadav, M. R.; Nagaoka, M.; Kashihara, M.; Zhong, R.-L.;
Miyazaki, T.; Sakaki, S.; Nakao, Y. J. Am. Chem. Soc. 2017, 139, 9423.
(b) Inoue, F.; Kashihara, M.; Yadav, M. R.; Nakao, Y. Angew. Chem.,
Int. Ed. 2017, 56, 13307.
(10) For other metal-catalyzed transformations of nitroarenes, see:
(a) Zheng, X.; Ding, J.; Chen, J.; Gao, W.; Liu, M.; Wu, H. Org. Lett.
2011, 13, 1726. (b) Peng, D.; Yu, A.; Wang, H.; Wu, Y.; Chang, J.
Tetrahedron 2013, 69, 6884. (c) Wang, H.; Yu, A.; Cao, A.; Chang, J.;
Wu, Y. Appl. Organomet. Chem. 2013, 27, 611. (d) Begum, T.; Mondal,
M.; Borpuzari, M. P.; Kar, R.; Gogoi, P. K.; Bora, U. Eur. J. Org. Chem.
2017, 3244. (e) Bahekar, S. S.; Sarkate, A. P.; Wadhai, V. M.; Wakte, P.
S.; Shinde, D. B. Catal. Commun. 2013, 41, 123. (f) Tian, H.; Cao, A.;
Qiao, L.; Yu, A.; Chang, J.; Wu, Y. Tetrahedron 2014, 70, 9107.
(11) (a) Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem.
Soc. 2009, 131, 3174. (b) Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani,
́
N. Bull. Korean Chem. Soc. 2010, 31, 582. (c) Alvarez-Bercedo, P.;
Martin, R. J. Am. Chem. Soc. 2010, 132, 17352. (d) Tobisu, M.;
Yamakawa, K.; Shimasaki, T.; Chatani, N. Chem. Commun. 2011, 47,
2946. (e) Mesganaw, T.; Nathel, N. F. F.; Garg, N. K. Org. Lett. 2012,
14, 2918. (f) Matsumura, T.; Niwa, T.; Nakada, M. Tetrahedron Lett.
2012, 53, 4313. (g) Cornella, J.; Gomez-Bengoa, E.; Martin, R. J. Am.
́
Chem. Soc. 2013, 135, 1997. (h) Ohgi, A.; Nakao, Y. Chem. Lett. 2016,
45, 45.
(12) Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am.
Chem. Soc. 2008, 130, 13552.
(13) (a) Spogliarich, R.; Zassinovich, G.; Mestroni, G.; Graziani, M. J.
Organomet. Chem. 1980, 198, 81. (b) Navarro, O.; Kaur, H.; Mahjoor,
P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (c) Yasui, K.; Higashino,
D
Org. Lett. XXXX, XXX, XXX−XXX