Abstract
Efficient conditions for Pd-catalyzed cross-coupling of sterically hindered aryl halides with nitromethane were developed to give corresponding aryl nitromethanes. The opportunity to carry out the reaction of polynitromethylation under these conditions was demonstrated, as well as to use the obtained products in the synthesis of bisnitrile oxides.
Similar content being viewed by others
References
N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
H. Feuer, A. T. Nielsen, Nitro Compounds: Recent Advances in Synthesis and Chemistry, VCH Publishers, New York, 1990.
S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovskii, Russ. Chem. Rev., 2020, 89, 1; DOI: https://doi.org/10.1070/RCR4908.
E. Marqués-López, P. Merino, T. Tejero, R. P. Herrera, Eur. J. Org. Chem., 2009, 2401; DOI: https://doi.org/10.1002/ejoc.200801097.
R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, M. Petrini, Chem. Rev., 2005, 105, 933; DOI: https://doi.org/10.1021/cr040602r.
F. A. Luzzio, Tetrahedron, 2001, 57, 915; DOI: https://doi.org/10.1016/S0040-4020(00)00965-0.
R. Ballini, A. Palmieri, P. Righi, Tetrahedron, 2007, 63, 12099; DOI: https://doi.org/10.1016/j.tet.2007.09.024.
T. A. Davis, J. N. Johnston, Chem. Sci., 2011, 2, 1076; DOI: https://doi.org/10.1039/C1SC00061F.
J. G. Greger, S. J. P. Yoon-Miller, N. R. Bechtold, S. A. Flewelling, J. P. MacDonald, C. R. Downey, E. A. Cohen, E. T. Pelkey, J. Org. Chem., 2011, 76, 8203; DOI: https://doi.org/10.1021/jo2013516.
V. Meyer, O. Stüber, Ber. Deutsch. Chem. Ges., 1872, 5, 203; DOI: https://doi.org/10.1002/cber.18720050165.
N. Kornblum, H. O. Larson, R. K. Blackwood, D. D. Mooberry, E. P. Oliveto, G. E. Graham, J. Am. Chem. Soc., 1956, 78, 1497; DOI: https://doi.org/10.1021/ja01588a059.
R. Ballini, L. Barboni, G. Giarlo, J. Org. Chem., 2004, 69, 6907; DOI: https://doi.org/10.1021/jo049048b.
W. D. Emmons, J. Am. Chem. Soc., 1957, 79, 5528; DOI: https://doi.org/10.1021/ja01577a053.
S. Rozen, M. Kol, J. Org. Chem., 1992, 57, 7342; DOI: https://doi.org/10.1021/jo00052a061.
W. D. Emmons, A. S. Pagano, J. Am. Chem. Soc., 1955, 77, 4557; DOI: https://doi.org/10.1021/ja01622a036.
D. S. Base, G. Vanajatha, Synth. Commun., 1998, 28, 4531; DOI: https://doi.org/10.1080/00397919808004517.
M. S. Denisov, M. V. Dmitriev, A. A. Gorbunov, V. A. Glushkov, Russ. Chem. Bull., 2019, 68, 2039; DOI: https://doi.org/10.1007/s11172-019-2664-3.
K. N. Gavrilov, I. V. Chuchelkin, V. K. Gavrilov, S. V. Zheglov, I. D. Firsin, V. M. Trunina, A. V. Maximychev, A. M. Perepukhov, Russ. Chem. Bull., 2021, 70, 336; DOI: https://doi.org/10.1007/s11172-021-3090-x.
A. A. Vasil’ev, A. S. Burukin, G. M. Zhdankina, S. G. Zlotin, Mendeleev Commun., 2021, 31, 400; DOI: https://doi.org/10.1016/j.mencom.2021.04.039.
E. M. Vogl, S. L. Buchwald, J. Org. Chem., 2002, 67, 106; DOI: https://doi.org/10.1021/jo010953v.
J. M. Fox, X. Huang, A. Chieffi, S. L. Buchwald, J. Am. Chem. Soc., 2000, 122, 1360; DOI: https://doi.org/10.1021/ja993912d.
A. E. Metz, S. Berritt, S. D. Dreher, M. C. Kozlowski, Org. Lett., 2012, 14, 760; DOI: https://doi.org/10.1021/ol203303b.
M. Zhang, J. Zhou, J. Kan, M. Wang, W. Su, M. Hong, Chem. Commun., 2010, 46, 5455; DOI: https://doi.org/10.1039/C0CC01029D.
M. Zhang, P. Hu, J. Zhou, G. Wu, S. Huang, W. Su, Org. Lett., 2013, 15, 1718; DOI: https://doi.org/10.1021/ol400507u.
D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron, 2002, 58, 2041; DOI: https://doi.org/10.1016/S0040-4020(02)00076-5.
R. R. Walvoord, S. Berritt, M. C. Kozlowski, Org. Lett., 2012, 14, 4086; DOI: https://doi.org/10.1021/ol301713j.
R. R. Walvoord, M. C. Kozlowski, J. Org. Chem., 2013, 78, 8859; DOI: https://doi.org/10.1021/jo401249y.
P. S. Gribanov, Y. D. Golenko, M. A. Topchiy, A. N. Philippova, N. Y. Kirilenko, N. V. Krivoshchapov, G. K. Sterligov, A. F. Asachenko, M. V. Bermeshev, M. S. Nechaev, Mendeleev Commun., 2018, 28, 323; DOI: https://doi.org/10.1016/j.mencom.2018.05.032.
P. S. Gribanov, G. A. Chesnokov, P. B. Dzhevakov, N. Y. Kirilenko, S. A. Rzhevskiy, A. A. Ageshina, M. A. Topchiy, M. V. Bermeshev, A. F. Asachenko, M. S. Nechaev, Mendeleev Commun., 2019, 29, 147; DOI: https://doi.org/10.1016/j.mencom.2019.03.009.
G. A. Chesnokov, A. A. Ageshina, A. V. Maryanova, S. A. Rzhevskiy, P. S. Gribanov, M. A. Topchiy, M. S. Nechaev, A. F. Asachenko, Russ. Chem. Bull., 2020, 69, 2370; DOI: https://doi.org/10.1007/s11172-020-3028-8.
E. V. Bermesheva, A. I. Wozniak, M. V. Bermeshev, A. F. Asachenko, M. A. Topchiy, M. S. Nechaev, M. P. Filatova, A. P. Khrychikova, Polymer Sci., Ser. B, 2020, 62, 319; DOI: https://doi.org/10.1134/S1560090420030021.
A. I. Wozniak, E. V. Bermesheva, F. A. Andreyanov, I. L. Borisov, D. P. Zarezin, D. S. Bakhtin, N. N. Gavrilova, I. R. Ilyasov, M. S. Nechaev, A. F. Asachenko, M. A. Topchiy, A. V. Volkov, E. S. Finkelshtein, X.-K. Ren, M. V. Bermeshev, Reactive and Functional Polymers, 2020, 149, 104513; DOI: https://doi.org/10.1016/j.reactfunctpolym.2020.104513.
E. V. Bermesheva, A. I. Wozniak, F. A. Andreyanov, G. O. Karpov, M. S. Nechaev, A. F. Asachenko, M. A. Topchiy, E. K. Melnikova, Y. V. Nelyubina, P. S. Gribanov, M. V. Bermeshev, ACS Catalysis, 2020, 10, 1663; DOI: https://doi.org/10.1021/acscatal.9b04686.
S. A. Rzhevskiy, M. A. Topchiy, V. N. Bogachev, A. A. Ageshina, L. I. Minaeva, G. K. Sterligov, M. S. Nechaev, A. F. Asachenko, Mendeleev Commun., 2021, 31, 478; DOI: https://doi.org/10.1016/j.mencom.2021.07.013.
S. A. Rzhevskiy, V. N. Bogachev, L. I. Minaeva, G. K. Sterligov, M. S. Nechaev, M. A. Topchiy, A. F. Asachenko, Mendeleev Commun., 2021, 31, 548; DOI: https://doi.org/10.1016/j.mencom.2021.07.037.
Pat. CN111718227A, 2020.
Pat. CN109837053A, 2019.
Pat. CN108441157A, 2018.
Pat. CN107739588A, 2018.
F. Neese, Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2018, 8, e1327; DOI: https://doi.org/10.1002/wcms.1327.
Pat. US5736748A, 1998.
Pat. WO 9703107 A1, 1997.
J. Hayashi, J. Furukawa, S. Yamashita, Nippon Gomu Kyokaishi, 1970, 43, 807; DOI: https://doi.org/10.2324/gomu.43.807.
J. Hayashi, J. Furukawa, S. Yamashita, Nippon Gomu Kyokaishi, 1970, 43, 818; DOI: https://doi.org/10.2324/gomu.43.818.
Pat. JP2010037288A, 2010.
M. J. Rhoad, P. J. Flory, J. Am. Chem. Soc., 1950, 72, 2216; DOI: https://doi.org/10.1021/ja01161a096.
K. Kurita, N. Hirakawa, T. Dobashi, Y. Iwakura, J. Polymer Sci.: Polymer Chem. Ed., 1979, 17, 2567; DOI: https://doi.org/10.1002/pol.1979.170170828.
R. R. Walvoord, M. C. Kozlowski, J. Org. Chem., 2013, 78, 8859; DOI: https://doi.org/10.1021/jo401249y.
F. M. Hauser, V. M. Baghdanov, J. Org. Chem., 1988, 53, 2872; DOI: https://doi.org/10.1021/jo00247a049.
M. Lőkös, P. Hegyes, S. Földeák, J. Organomet. Chem., 1984, 275, 27; DOI: https://doi.org/10.1016/0022-328X(84)80573-2.
R. R. Walvoord, M. C. Kozlowski, Tetrahedron Lett., 2015, 56, 3070; DOI: https://doi.org/10.1016/j.tetlet.2014.12.105.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 59–63, January, 2022.
This work was financially supported by the Russian Science Foundation (Project No. 17-13-01076). The synthesis of nitrile oxides was carried out within the framework of the State Assignment to A. V. Topchiev Institute of Petrochemical Synthesis of the Russian Academy of Sciences.
No human or animal subjects were used in this study.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Topchiy, M.A., Lysenko, A.N., Rasskazova, M.A. et al. Arylation of nitromethane with sterically hindered aryl halides. Russ Chem Bull 71, 59–63 (2022). https://doi.org/10.1007/s11172-022-3376-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-022-3376-7