Abstract
The results of studies in the area of oxidative functionalization of hydrocarbons of the adamantane series over the last two decades have been summarized and oxidation, carbonylation, and carboxylation reactions involving oxidizing agents and catalysts of various types, possible reaction mechanisms, properties and promising directions of the use of the obtained products have been considered.
Similar content being viewed by others
References
S. Landa and V. Machacek, Collect. Czech. Chem. Commun. 5, 1 (1933).
R. Lin and Z. A. Wilk, Fuel 74, 1512 (1995).
A. A. Fokin, P. R. Schreiner, and H. Schwerfeger, Angew. Chem., Int. Ed. Engl. 47, 1022 (2008).
M. A. Gunawan, J.-C. Hierso, D. Poinsot, et al., New J. Chem. 38, 28 (2014).
E. I. Bagrii, R. E. Safir, and Yu. A. Arinicheva, Pet. Chem. 50, 1 (2010).
A. I. Nekhaev, E. I. Bagrii, and A. L. Maksimov, Pet. Chem. 51, 86 (2011).
I. K. Moiseev, N. V. Makarova, and M. N. Zemtsova, Usp. Khim. 68, 1102 (1999).
E. A. Shokova and V. V. Kovalev, Usp. Khim. 80, 927 (2011).
G. N. Gordadze, Pet. Chem. 48, 241 (2008).
I. S. Morozov, V. I. Petrov, and S. A. Sergeeva, Pharmacology of Adamantanes (Volgogradskaya Meditsinskaya Akademiya, Volgograd, 2001) [in Russian].
A. K. Sutara and C.-C. Lin, Coord. Chem. Rev. 253, 1926 (2009).
T. Newhouse and P. S. Baran, Angew. Chem., Int. Ed. Engl. 50, 3362 (2011).
E. A. Shokova and V. V. Kovalev, Russ. J. Org. Chem. 48, 1007 (2012).
K. A. Agnew-Francis and C. M. Williams, Adv. Synth. Catal. (2016). doi 10.1002/adsc.201500949
E. I. Bagrii, Adamantanes (Nauka, Moscow, 1989) [in Russian].
A. A. Fokin and A. G. Yurchenko, in Panorama of Modern Russian Chemistry: Advances in Adamantane Chemistry (Khimiya, Moscow, 2007), p. 42 [in Russian].
V. V. Vasil’eva, A. I. Nekhaev, I. Yu. Shchapin, and E. I. Bagrii, Kinet. Catal. 47, 610 (2006).
I. Yu. Shchapin, V. V. Vasil’eva, A. I. Nekhaev, and E. I. Bagrii, Kinet. Catal. 47, 624 (2006).
I. Yu. Shchapin, A. I. Nekhaev, and E. I. Bagrii, in Panorama of Modern Russian Chemistry: Advances in Adamantane Chemistry (Khimiya, Moscow, 2007) [in Russian].
G. A. Olah, O. Farooq, and G. K. S. Prakash, Activation and Functionalization of Alkanes, Ed. by C. L. Hill (Wiley, New York 1989), p. 27.
S. N. Khadzhiev, Yu. P. Suvorov, V. R. Zinov’ev, et al., Cracking of Petroleum Fractions on Zeolite Catalysts (Khimiya, Moscow, 1982) [in Russian].
K. Dobek, A. Maciejewski, J. Karolczak, and W. Augustyniak, J. Phys. Chem. A 106, 2789.
A. Company, J. Lloret, L. Gómez, and M. Costas, Catalysis by Metal Complexes, vol. 38: Alkane C–H Activation by Single-Site Metal Catalysis, Ed. by P. J. Pérez (Springer, Dordrecht, 2012), p. 147.
Y. Arai, T. Ouchi, K. Yoshida, and M. Kadota, JP Appl. No. 2004339105 (2004).
T. Arai, T. Onozawa, S. Niiyama, and K. Yoshida, JP Appl. No. 2004051497 (2004).
K. Wakui and K. Okamoto, JP Appl. No. 2004307430 (2004).
A. I. Nekhaev, V. G. Zaikin, and E. I. Bagrii, Neftekhimiya 35, 343 (1995).
E. I. Bagrii and A. I. Nekhaev, Neftekhimiya 36, 483 (1996).
A. I. Nekhaev, V. G. Zaikin, and E. I. Bagrii, Pet. Chem. 38, 19 (1998).
Y. Furutani, H. Kandori, M. Kawano, et al., J. Am. Chem. Soc. 131, 4764 (2009).
M. Drees and T. Strassner, Org. Chem. 71, 1755 (2006).
M. Bonchio, G. Scorrano, P. Toniolo, et al., Adv. Synth. Catal. 344, 841 (2002).
M. Yamaguchi, M. Tomizawa, K. Takagaki, et al., Catal. Today 117, 206 (2006).
M. Yamaguchi, H. Kousaka, S. Izawa, et al., Inorg. Chem. 45, 8342 (2006).
M. Costas, Coord. Chem. Rev. 255, 2912 (2011).
A. A. Guedes, J. R. L. Smith, O. R. Nascimento, et al., J. Braz. Chem. Soc. 16, 835 (2005).
J. R. Carney, B. R. Dillon, and S. P. Thomas, Eur. J. Org. Chem., No. 23, 3912 (2016).
A. Rezaeifard, M. Jafarpour, A. Farrokhi, et al., RSC Adv. 6, 64640 (2016).
M. V. Avdeev, E. I. Bagrii, G. B. Maravin, et al., Pet. Chem. 40, 391 (2000).
S. Tangestaninejad, M. Moghadam, V. Mirkhani, and H. Kargar, Ultrasonics Sonochem. 13, 32 (2006).
W. Nam, S.-E. Park, I. K. Lim, et al., J. Am. Chem. Soc. 125, 14674 (2003).
A. Pariyar, S. Bose, A. N. Biswas, et al., Catal. Commun. 32, 23 (2013).
P.-P. H. J. M. Knops-Gerrits, and W. A. Goddard, III, Catal. Today 81, 263 (2003).
H. Jaafar, B. Bertrand Vileno, A. Thibon, and D. Mandon, Dalton Trans. 40, 92 (2011).
T. Ohno, T. Mitsui, and M. Matsumura, J. Photochem. Photobiol., A 160, 3 (2003).
G. Bianchini, M. Crucianelli, F. de Angelis, et al., Tetrahedron Lett. 46, 2427 (2005).
V. Conte and B. Floris, Inorg. Chim. Acta 363, 1935 (2010).
G. B. Shul’pin, A. R. Kudinov, L. S. Shul’pina, and E. A. Petrovskaya, J. Organomet. Chem. 691, 837 (2006).
M. V. Kirillova, Y. N. Kozlov, L. S. Shul’pina, et al., J. Catal. 268, 26 (2009).
G. B. Shul’pin, A. E. Shilov, and G. Süss-Fink, Tetrahedron Lett. 42, 7253 (2001).
G. Süss-Fink, L. Gonzalez, and G. B. Shul’pin, Appl. Catal., A 217, 111 (2001).
E. A. Turitsyna, O. N. Gritsenko, and A. A. Shteinman, Kinet. Catal. 48, 53 (2007).
J. Martin-Caballero, A. San José Wéry., S. Reinoso, et al., Inorg. Chem. 55, 4970 (2016).
F. Li, M. Wang, C. Ma, et al., Dalton Trans., No. 20, 2427 (2006).
M. Sankaralingam and M. Palaniandavar, Polyhedron 67, 171 (2014).
A. Pariyar, S. Bose, A. N. Biswas, et al., Catal. Sci. Technol. 4, 3180 (2014).
I. Prat, A. Company, V. Postils, et al., Chem.-Eur. J. 19, 6724 (2013).
F. C. Skrobot, I. L. Rosa, A. P. A. Marques, et al., J. Mol. Catal. A 237, 86 (2005).
D. Prieto-Centurion and J. M. Notestein, J. Catal. 279, 103 (2011).
D. Prieto-Centurion, A. M. Boston, and J. M. Notestein, J. Catal. 296, 77 (2012).
E. Kockrick, T. Lescouet, E. V. Kudrik, et al., Chem. Commun. 47, 1562 (2011).
S. Tanase, P. Marques-Gallego, W. R. Browne, et al., Dalton Trans., No. 15, 2026 (2008).
P. C. A. Bruijnincx, I. L. C. Buurmans, Y. Huang, et al., Inorg. Chem. 50, 9243 (2011).
K. Takaki, J. Yamamoto, K. Komeyama, et al., Bull. Chem. Soc. Jpn. 77, 2251 (2004).
K. M. Parida and S. K. Dash, J. Hazard. Mater. 179, 642 (2010).
O. Perraud, A. B. Sorokin, J.-P. Dutasta, and A. Martinez, Chem. Commun. 49, 1288 (2013).
A. Bordoloi, A. Vinu, and S. B. Halligudi, Appl. Catal., A 333, 143 (2007).
E. N. Karaulova, E. I. Bagrii, and V. G. Zaikin, Neftekhimiya 34, 195 (1994).
D. Dondi, A. M. Cardarelli, M. Fagnoni, and A. Albini, Tetrahedron 62, 5527 (2006).
T. Joseph, M. Hartmann, S. Ernst, and S. B. Halligudi, J. Mol. Catal. A 207, 131 (2004).
H. Kobayashi and I. Yamanaka, J. Mol. Catal. A 294, 37 (2008).
H. Kobayashi and I. Yamanaka, J. Mol. Catal. A 294, 43 (2008).
T. Mitsudome, N. Nosaka, K. Mori, et al., Chem. Lett. 34, 1626 (2005).
M. Balamurugan, R. Mayilmurugan, E. Suresh, and M. Palaniandavar, Dalton Trans. 40, 9413 (2011).
M. Sankaralingam, P. Vadivelu, E. Suresh, and M. Palaniandavar, Inorg. Chim. Acta 407, 98 (2013).
E. Tordin, M. List, U. Monkowius, et al., Inorg. Chim. Acta 402, 90 (2013).
A. N. Biswas, P. Das, A. Agarwala, et al., J. Mol. Catal. A 326, 94 (2010).
S. Bose, A. Pariyar, A. N. Biswas, et al., Catal. Commun. 12, 1193 (2011).
S. Bose, A. Pariyar, A. N. Biswas, et al. J. Mol. Catal. A 332, 1 (2010).
A. N. Biswas, A. Pariyar, S. Bose, et al., Catal. Commun. 11, 1008 (2010).
T. Ohno, T. Mitsui, and M. Matsumura, J. Photochem. Photobiol., A 160, 3 (2003).
Y. Terutaka, JP Appl. No. 2004143032 (2004).
I. Yamanaka, T. Gomi, T. Nabeta, and K. Otsuka, Chem. Lett. 34, 1486 (2005).
I. Yamanaka, Y. Suzuki, and M. Toida, Catal. Today 157, 286 (2010).
G. Bianchini, M. Crucianelli, F. de Angelis, et al., Tetrahedron Lett. 45, 2351 (2004).
S.-M. Yiu, W.-L. Man, and T.-C. Lau, J. Am. Chem. Soc. 130, 10821 (2008).
R. I. Khusnutdinov, N. A. Shchadneva, L. F. Mukhametshina, and U. M. Dzhemilev, Russ. J. Org. Chem. 45, 1137 (2009).
L. D’Accolti, P. Kang, S. Khan, et al., Tetrahedron Lett. 43, 4649 (2002).
S. A. Grabovsky, A. V. Antipin, and N. N. Kabal’nova, Kinet. Catal. 45, 809 (2004).
L.-Q. Cui, K. Liu, and C. Zhang, Org. Biomol. Chem. 9, 2258 (2011).
H. M. Neu, V. V. Zhdankin, and V. N. Nemykin, Tetrahedron Lett. 51, 6545 (2010).
A. A. Fokin, T. S. Zhuk, A. E. Pashenko, et al., J. Org. Chem. 79, 1861 (2014).
M. Sumida, Y. Nishimura, K. Yanagisawa, and T. Isobe, JP Appl. No. 2004026778 (2004).
Y. Ishii and S. Sakaguchi, Catal. Today 117, 105 (2006).
Z. Du, Z. Sun, W. Zhang, et al., Tetrahedron Lett. 50, 1677 (2009).
N. Theyssen, Z. Hou, and W. Leitner, Chem.-Eur. J. 12, 3401 (2006).
Yu. N. Klimochkin, O. V. Abramov, I. K. Moiseev, et al., Pet. Chem. 40, 415 (2000).
S. Shinachi, H. Yahiro, K. Yamaguchi, and N. Mizuno, Chem.-Eur. J. 10, 6489 (2004).
N. A. Fokina, B. A. Tkachenko, A. Merz, et al., Eur. J. Org. Chem., No. 28, 4738 (2007).
P. R. Schreiner, N. A. Fokina, B. A. Tkachenko, et al., J. Org. Chem. 71, 6709 (2006).
A. A. Fokin, P. R. Schreiner, N. A. Fokina, et al., J. Org. Chem. 71, 8532 (2006).
A. I. Nekhaev and E. I. Bagrii, Izv. Akad. Nauk, Ser. Khim., No. 2, 341 (2002).
A. I. Nekhaev, R. S. Borisov, V. G. Zaikin, and E. I. Bagrii, Pet. Chem. 42, 238 (2002).
A. I. Nekhaev, R. S. Borisov, V. G. Zaikin, and E. I. Bagrii, Pet. Chem. 42, 310 (2002).
R. E. White, M. McCarthy, K. D. Egeberg, and S. G. Sligar, Arch. Biochem. Biophys. 228, 493 (1984).
I. I. Starovoitov, E. I. Bagrii, A. V. Slepen’kin, et al., Dokl. Akad. Nauk 335, 241 (1994).
E. I. Bagrii, I. I. Starovoitov, A. V. Slepen’kin, et al., in Panorama of Modern Russian Chemistry: Advances in Adamantane Chemistry (Khimiya, Moscow, 2007), p. 291 [in Russian].
K. Mitsukura, Y. Kondo, T. Yoshida, and T. Nagasawa, Appl. Microbiol. Biotechnol. 71, 502 (2006).
K. Mitsukura, H. Sakamoto, H. Kubo, et al., J. Biosci. Bioeng. 109, 550 (2010).
T. S. Zhuk, M. Goldmann, J. Hofmann, et al., J. Mol. Catal. B: Enzym. 122, 87 (2015).
O. Farooq, M. Marcell, G. K. S. Prakash, and G. A. Olah, J. Am. Chem. Soc. 110, 864 (1988).
J. Akhrem, J. Churilova, S. Bernadyuk, and M. Vol’pin, Tetrahedron Lett. 37, 5775 (1996).
M. Oshita and N. Chatani, Org. Lett. 6, 4323 (2004).
M. V. Luzgin, K. Thomas, J. Vangestel, J. P. Gilson, A. G. Stepanov, J. Catal. 223, 290 (2004).
E. Quintanilla, J. Z. Davalos, J. L. M. Abboud, et al., Chem.-Eur. J. 11, 1826 (2005).
T. Iwahama and T. Kubo, JP Appl. No. 2004189697 (2004).
G. S. Lee, J. N. Bashara, G. Sabih, et al., Org. Lett. 6, 1705 (2004).
S. J. Rowland, R. Clough, C. E. West, et al., Rapid Commun. Mass Spectrom. 25, 2573 (2011).
Y. Li, K. Dong, F. Zhu, et al., Angew. Chem. 128, 7343 (2016).
T. Tanaka and S. Yamaguchi, JP Appl. No. 2004189702 (2004).
R. Vicha and M. Potacek, Tetrahedron 61, 83 (2005).
K. Tanaka, JP Appl. No. 2004269387 (2004).
T. Kagayama, M. Nakayama, R. Oka, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 47, 5459 (2006).
S. N. Voloboev, L. N. Butenko, and I. A. Novakov, Russ. J. Gen. Chem. 71, 1121 (2001).
N. V. Averina, O. N. Zefirova, N. S. Zefirov, et al., Russ. J. Org. Chem. 40, 1437 (2004).
S. P. Elangovan, K. Inoue, T. Okubo, et al., Ind. Eng. Chem. Res. 46, 1039 (2007).
N. G. Kozlov, E. A. Dikusar, and V. I. Potkin, Russ. J. Appl. Chem. 76, 105 (2003).
E. A. Dikusar, N. G. Kozlov, V. I. Potkin, and N. V. Kovgaenko, Khim. Prirod. Soedin., No. 3, 215 (2003).
E. A. Dikusar, N. G. Kozlov, V. I. Potkin, A. P. Yuvchenko, N. V. Kovganko, Russ. J. Org. Chem. 40, 346 (2004).
E. A. Dikusar and N. G. Kozlov, Russ. J. Org. Chem. 43, 1263 (2007).
E. A. Dikusar, V. I. Potkin, A. P. Yuvchenko, et al., Russ. J. Gen. Chem. 77, 1598 (2007).
E. N. Ulomskii, S. L. Deev, A. V. Tkachev, et al., Russ. J. Org. Chem. 38, 272 (2002).
V. G. Tsypin, V. V. Kachala, B. I. Ugrak, and E. L. Golod, Russ. J. Org. Chem. 38, 90 (2002).
E. A. Shokova, A. E. Motornaya, A. K. Shestakova, and V. V. Kovalev, Tetrahedron Lett. 45, 6465 (2004).
E. Shokova, V. Tafeenko, and V. Kovalev, Tetrhedron Lett 43, 5153 (2002).
N. I. Miryan, S. D. Isaev, A. G. Yurchenko, et al., Russ. J. Org. Chem. 38, 188 (2002).
A. K. Shiryaev, Chem. Heterocycl. Compd. 40, 114 (2004)
S. P. Elangovan, K. Inoue, T. Yokoi, et al., Catal. Today 131, 367 (2008).
M. S. Yusubov, V. N. Nemykin, and V. V. Zhdankin, Tetrahedron 66, 5745 (2010).
P. Strazzolini, N. Misuri, and P. Polese, Tetrahedron Lett. 46, 2075 (2005).
E. A. Ivleva, V. S. Gavrilova, and Yu. N. Klimochkin, Russ. J. Org. Chem. 52, 785 (2016).
B. I. No, G. M. Butov, V. M. Mokhov, and G. Yu. Parshin, Russ. J. Org. Chem. 38, 295 (2002).
B. I. No, G. M. Butov, V. M. Mokhov, and G. Yu. Parshin, Zh. Org. Khim. 38, 1428 (2002).
B. I. No, G. M. Butov, V. M. Mokhov, and G. Yu. Parshin, Russ. J. Org. Chem. 39, 1668 (2003).
G. M. Butov, V. M. Mokhov, G. Yu. Parshin, and R. U. Kunaev, Russ. J. Org. Chem. 45, 1864 (2009).
G. M. Butov, V. V. Pershin, and V. V. Burmistrov, Russ. J. Org. Chem. 47, 606 (2011).
G. M. Butov and V. M. Mokhov, Russ. J. Org. Chem. 50, 447 (2014).
I. A. Novikova, T. N. Dolgopolova, A. D. Apryatkin, et al., Neftekhimiya 33, 59 (1993).
V. S. Bilyavskii, A. I. Khil’chevskii, A. E. Petrenko, and L. V. Golovko, Katal. Neftekhim., No. 9/10, 103 (2001).
E. I. Bagrii and G. B. Maravin, Pet. Chem. 53, 419 (2013).
E. A. Ivleva, M. R. Baimuratov, V. S. Gavrilova, et al., Pet. Chem. 55, 673 (2015).
K. Ohyama, Y. Fukahori, K. Nakashima, et al., J. Chromatogr. A 1217, 1501 (2010).
K. Wang, R. Yin, J. Nie, and Q. Yu, Mater. Sci. Eng. C 32, 1141 (2012).
H. Zhu, J. Guo, C. Yang, et al., Synth. Commun. 43, 1161 (2013).
X.-J. Xu, J.-W. Guo, and X. Zhong, Chin. Chem. Lett. 25, 367 (2014).
S. Kobayashi, H. Kataoka, T. Ishizone, et al., React. Funct. Polym. 69, 409 (2009).
T. Nakano and Y. Funaki, US Patent No. 6391520 (2002).
J. Ohshita, K. Hino, K. Inata, et al., Polymer 48, 4301 (2007).
Y. Hattori, T. Miyajima, M. Sakai, et al., Polymer 49, 2825 (2008).
B. Zhang, S. Zhang, Z. Weng, et al., J. Power Sources 325, 801 (2016).
R. N. Tiwari and M. Yoshimura, AIP Adv. 6, 065120 (2016).
D. **ang, H. Chen, W. Zhu, and H. **ao, Can. J. Chem. 94, 667 (2016).
S. Ando, A. Yoshida, and K. Nagai, Polym. Eng. Sci. 56, 1191 (2016).
M. Tada, US Patent Appl. No. 2016/0072064 (2016).
N. G. Artsimovich, E. I. Bagrii, A. M. Boronin, et al., RU Patent No. 2077339 (1997).
D. V. Osipov, M. R. Demidov, V. A. Osyanin, M. Yu. Skomorokhov, Yu. N. Klimochkin, Russ. J. Org. Chem. 52, 906 (2016).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © E.I. Bagrii, A.I. Nekhaev, A.L. Maksimov, 2017, published in Neftekhimiya, 2017, Vol. 57, No. 2, pp. 123–137.
Rights and permissions
About this article
Cite this article
Bagrii, E.I., Nekhaev, A.I. & Maksimov, A.L. Oxidative functionalization of adamantanes (review). Pet. Chem. 57, 183–197 (2017). https://doi.org/10.1134/S0965544117020128
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0965544117020128