Abstract
The modern trends in the development of synthetic approaches to the preparation of organic symmetrical and unsymmetrical disulfides are reviewed. The main trend in the synthesis of disulfides is the transition from the reactions involving metal-containing catalysts to the use of physical methods for the activation of sulfur substrates. The main attention is given to the works published since 2013 to the present time and devoted to the synthesis of disulfides in the presence of transition and nontransition metal complexes and organic and inorganic oxidants, as well as under the electric current action and photo- or microwave irradiation.
REFERENCES
Witt, D., Synthesis, 2008, vol. 16, p. 2491. https://doi.org/10.1055/s-2008-1067188
Mandal, B. and Basu, B., RSC Adv., 2014, vol. 4, p. 13854. https://doi.org/10.1039/C3RA45997G
Wang, M. and Jiang, X., Top Curr. Chem., 2018, vol. 376, no. 14, p. 285. https://doi.org/10.1007/s41061-018-0192-5
Ong, C.L., Khaligh, N.G., and Juan, J.C., Curr. Org. Chem., 2020, vol. 24, no. 5, p. 550. https://doi.org/10.2174/1385272824666200221111120
Ong, C.L., Titinchi, S., Juan, J.C., et al., Helv. Chim. Acta, 2021, vol. 104, no. 8, p. e2100053. https://doi.org/10.1002/hlca.202100053
Pereira Monteiro, C.J., Ferreira Faustino, M.A., Pinho Morgado Silva Neves, M.d.G., et al., Catalysts, 2021, vol. 11, p. 122. https://doi.org/10.3390/catal11010122
Sanz, R., Aguado, R., Pedrosa, M.R., et al., Synthesis, 2002, vol. 7, p. 0856. https://doi.org/10.1055/s-2002-28520
Pan, Y., Chen, W.X., Lu, S.F., and Zhang, Y.F., Dyes Pigm., 2005, vol. 66, p. 115. https://doi.org/10.1016/j.dyepig.2004.09.018
Huang, H., Asha, J., and Kang, J.Y., Org. Biomol. Chem., 2018, vol. 16, p. 4236. https://doi.org/10.1039/c8ob00908b
Reid, N. and Barat, R. Chem. Eng. Commun., 2016, vol. 203, p. 714. https://doi.org/10.1080/00986445.2015.1067802
Huang, X., Chen, Y., Zhen, S., et al., J. Org. Chem., 2018, vol. 83, no. 14, p. 7331. https://doi.org/10.1021/acs.joc.7b02718
Vashurin, A., Kuzmin, I., Razumov, M., et al., J. Porphyrins Phthalocyanines, 2015, vol. 19, no. 11, p. 1159. https://doi.org/10.1142/S1088424615500911
Bricker, J.C. and Laricchia, L., Top Catal., 2012, vol. 55, p. 1315. https://doi.org/10.1007/s11244-012-9913-0
Chauhan, D.K., Patnam, P.L., Ganguly, S.K., et al., RSC Adv., 2016, vol. 6, p. 51983. https://doi.org/10.1039/C6RA06842A
Dou, Y., Huang, X., Wang, H., et al., Green Chem., 2017, vol. 19, p. 2491. https://doi.org/10.1039/C7GC00401J
Golchoubian, H. and Hosseinpoor, F., Catal. Commun., 2007, vol. 8, p. 697. https://doi.org/10.1016/j.catcom.2006.08.036
Nikoorazm, M., Ghorbani-Choghamarani, A., Ghorbani, F., et al., J. Porous. Mater., 2015, vol. 22, p. 261. https://doi.org/10.1007/s10934-014-9892-6
Nikoorazm, M., Ghorbani-Choghamarani, A., Mahdavi, H., et al., Microporous Mesoporous Mat., 2015, vol. 211, p. 174. https://doi.org/10.1016/j.micromeso.2015.03.011
Ardakani, M.H., Saeednia, S., and Sabet, M., Silicon, 2019, vol. 11, p. 1775. https://doi.org/10.1007/s12633-018-9992-z
Ghorbani-Choghamarani, A., Tahmasbi, B., Arghand, F., et al., RSC Adv., 2015, vol. 5, p. 92174. https://doi.org/10.1039/C5RA14974F
Toma, A.M., Raţ, C.I., Pavel, O.D., et al., Catal. Sci. Technol., 2017, vol. 7, p. 5343. https://doi.org/10.1039/c7cy00521k
Gaur, R., Yadav, M., Gupta, R., et al., ChemistrySelect, 2018, vol. 3, p. 2502. https://doi.org/10.1002/slct.201703020
Eshtiagh-Hosseini, H., Tabari, T., Takjoo, R., et al., Synth. React. Inorg., Met.-Org., Nano-Met. Chem., 2013, vol. 43, p. 264. https://doi.org/10.1080/15533174.2012.740719
Moeini, M., Molaei, S., and Ghadermazi, M., J. Mol. Struct., 2021, vol. 1246, p. 131071, https://doi.org/10.1016/j.molstruc.2021.131071
Molaei, S. and Ghadermazi, M., Appl. Organometal. Chem., 2019, vol. 34, p. e5328. https://doi.org/10.1002/aoc.5328
Iali, W., Suleiman, R.K., and El Ali, B., Appl. Organomet. Chem., 2022, vol. 36, p. e6597. https://doi.org/10.1002/aoc.6597
Suzuki, T., Chem. Rev., 2011, vol. 111, no. 3, p. 1825. https://doi.org/10.1021/cr100378r
Tanaka, K. and Ajiki, K., Tetrahedron Lett., 2004, vol. 45, p. 25. https://doi.org/10.1016/j.tetlet.2003.10.120
Tanaka, K. and Ajiki, K., Tetrahedron Lett., 2004, vol. 45, p. 5677. https://doi.org/10.1016/j.tetlet.2004.05.092
Guo, J., Zha, J., Zhang, T., et al., Org. Lett., 2021, vol. 23, no. 8, p. 3167. https://doi.org/10.1021/acs.orglett.1c00858
Corma, A., Rodenas, T., and Sabater, M.J., Chem. Sci., 2012, vol. 3, p. 398. https://doi.org/10.1039/C1SC00466B
Qiu, X., Yang, X., Zhang, Y., et al., Org. Chem. Front., 2019, vol. 6, p. 2220. https://doi.org/10.1039/C9QO00239A
Reddy, R.J., Waheed, M., and Kumar J.J., RSC Adv., 2018, vol. 8, p. 40446. https://doi.org/10.1039/C8RA06938G
Jiang, Y., Qin, Y., Xie, S., et al., Org. Lett., 2009, vol. 11, p. 5250. https://doi.org/10.1021/ol902186d
Islam, S. and Paul, S., RSC Adv., 2016, vol. 6, p. 95753. https://doi.org/10.1039/C6RA19832E
Dhakshinamoorthy, A., Alvaro, M., and Garcia, H., Chem. Commun., 2010, vol. 46, p. 6476. https://doi.org/10.1039/C0CC02210A
Saxena, A., Kumar, A., and Mozumdar, S., J. Mol. Catal. A: Chem., 2007, vol. 269, p. 35. https://doi.org/10.1016/j.molcata.2006.12.042
Soleiman-Beigi, M., Yavarib, I., and Sadeghizadeh, F., RSC Adv., 2015, vol. 5, p. 87564. https://doi.org/10.1039/C5RA16879A
Wang, G., Jia, J., He, Y., et el., RSC Adv., 2022, vol. 12, p. 18407. https://doi.org/10.1039/D2RA02255A
Wang, F., Chen, Y., Rao, W., et al., Nature Comm., 2022, vol. 13, p. 2588. https://doi.org/10.1038/s41467-022-30256-0
Chen, Y., Sheng, D., Wang, F., et al., Org. Chem. Front., 2022, vol. 9, p. 4962. https://doi.org/10.1039/D2QO00945E
Deng, S.-R., Wu, T., Hu, G.-Q., et al., Synth. Comm., 2007, vol. 37, p. 71. https://doi.org/10.1080/00397910600978101
Priefer, R., Lee, Y.J., Barrios, F., et al., J. Am. Chem. Soc., 2002, vol. 124, no. 20, p. 5626. https://doi.org/10.1021/ja025823y
Tetsuo, A., Takeshi, A., Naomichi, F., et al., Bull. Chem. Soc. Japan, 1976, vol. 49, p. 1441. https://doi.org/10.1246/bcsj.49.1441
Steinfatt, I., Hoffmann, G.G., Brouwer, L., et al., Phosphorus Sulfur Silicon Relat. Elem., 1998, vol. 134, p. 31. https://doi.org/10.1080/10426509808545451
Ali, M.H. and McDermott, M., Tetrahedron Lett., 2002, vol. 43, no. 35, p. 6271. https://doi.org/10.1016/S0040-4039(02)01220-0
Kirihara, M., Asai, Y., Ogawa, S., et al., Synthesis, 2007, vol. 21, p. 3286. https://doi.org/10.1055/s-2007-990800
Rattanangkool, E., Krailat, W., Vilaivan, T., et al., Eur. J. Org. Chem., 2014, vol., 22, p. 4795. https://doi.org/10.1002/ejoc.201402180
Shi, Y., Chen, S.-P., Zhang, F., et al., ChemistrySelect, 2018, vol. 3, p. 997. https://doi.org/10.1002/slct.201702614
Karimi, B., Hazarkhani, H., and Zareyee, D., Synthesis, 2002, vol. 17, p. 2513. https://doi.org/10.1055/s-2002-35634
Leino, R. and Lönnqvist, J.-E., Tetrahedron Lett., 2004, vol. 45, p. 8489. https://doi.org/10.1016/j.tetlet.2004.09.100
Hajipour, A.R., Mallakpour, S.E., and Adibi, H., J. Org. Chem., 2002, vol. 67, no. 24, p. 8666. https://doi.org/10.1021/jo026106p
Chen, F.E., Lu, Y.-W., He, Y.-P., et al., Synth. Comm., 2002, vol. 32, p. 3487. https://doi.org/10.1081/SCC-120014782
Karimi, B. and Zareyee, D., Synlett., 2002, vol. 2, p. 0346. https://doi.org/10.1055/s-2002-19764
Xiao, H., Chen, J., Liu, M., et al., Phosphorus Sulfur Silicon Relat. Elem., 2009, vol. 184, p. 2553. https://doi.org/10.1080/10426500802529051
Harusawa, S., Yoshida, K., Kojima, C., et al., Tetrahedron, 2004, vol. 60, p. 11911. https://doi.org/10.1016/j.tet.2004.09.109
Mu, Y.Q., Nodwell, M., and Pace, J.L., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 735. https://doi.org/10.1016/j.bmcl.2003.11.040
Morais, G.R. and Falconer, R.A., Tetrahedron Lett., 2007, vol. 48, p. 7637. https://doi.org/10.1016/j.tetlet.2007.08.106
Yue, H., Wang, J., Xie, Z., et al., ChemistrySelect, 2020, vol. 5, p. 4273. https://doi.org/10.1002/slct.202000638
Misra, A.K. and Agnihotri, G., Synth. Comm., 2004, vol. 34, p. 1079. https://doi.org/10.1081/SCC-120028640
Tajbakhsh, M., Hosseinzadeh, R., and Shakoori, A., Tetrahedron Lett., 2004, vol. 45. p. 1889. https://doi.org/10.1016/j.tetlet.2004.01.006
Azeredo, J.B., Thedy, M.E.C., Godoi, M., et al., Tetrahedron Lett., 2022., vol. 100, p. 153883.
Zhang, Z., Lan, X., Zhang, X., et al., Asian J. Org. Chem., 2023, vol. 12, no. 3, p. e202300009. https://doi.org/10.1002/ajoc.202300009
Kast, C.E. and Bernkop-Schnürch, A., Biomaterials, 2001, vol. 22, p. 2345. https://doi.org/10.1016/S0142-9612(00)00421-X
Yang, F., Wang, W., Li, K., et al., Tetrahedron, 2017, vol. 58, p. 218. https://doi.org/10.1016/j.tetlet.2016.12.007
Mino, R.H. and Stellenboom, C.N., J. Org. Chem., 2006, vol. 71, no. 21, p. 8268. https://doi.org/10.1021/jo060693n
Lo, Y.-H., Wang, L.-Y., and Duraisamy, T., et al., Asian J. Org. Chem., 2022, vol. 11, no. 6., p. e202200203. https://doi.org/10.1002/ajoc.202200203
Dong, B., Chen, Y., Xie, S., et al., Org. Biomol. Chem., 2023, vol. 21, p. 930. https://doi.org/10.1039/D2OB02124B
Yuan, J., Liu, C., and Lei, A., Org. Chem. Front., 2015, vol. 2, no. 6, p. 677. https://doi.org/10.1039/C5QO00027K
Xu, Y., Shi, X., and Wu, L., RSC Adv., 2019, vol. 9, p. 24025. https://doi.org/10.1039/C9RA04242C
Vandavasi, J.K., Hu, W.-P., Chen, C.-Y., et al., Tetrahedron, 2011, vol. 67, p. 8895. https://doi.org/10.1016/j.tet.2011.09.071
Lo, W.-S., Hu, W.-P., Lo, H.-P., et al., Org. Lett., 2010, vol. 12, p. 5570. https://doi.org/10.1021/ol102455x
Brinker, U.H., Tyner, M., and Jones, W.M., Synthesis, 1975, vol. 1975, no. 10, p. 671. https://doi.org/10.1055/s-1975-23885
Burmistrova, D.A., Smolyaninov, I.V., and Berberova, N.T., Russ. Chem. Bull., 2020, vol. 69, no. 5, p. 990. https://doi.org/10.1007/s11172-020-2860-1
Burmistrova, D.A., Kuzmin, V.V., Smolyaninov, I.V., et al., ChemChemTech., 2019, vol. 62, no. 12, p. 57. https://doi.org/10.6060/ivkkt.20196212.6027
Song, L., Li, W., Duan, W., et al., Green Chem., 2019, vol. 21, p. 1432. https://doi.org/10.1039/C9GC00091G
Bao, M. and Shimizu, M., Tetrahedron, 2003, vol. 59, p. 9655. https://doi.org/10.1016/j.tet.2003.09.080
Ayodele, E.T., Olajire, A.A., Amuda, O.S., et al., Bull. Chem. Soc. Ethiop., 2003, vol. 17, p. 53. https://doi.org/10.4314/bcse.v17i1.61731
Zhang, J., Li, S., Zhang, D., et al., Org. Lett., 2010, vol. 12, p. 4208. https://doi.org/10.1021/ol101863s
Mancebo-Aracil, J., Casagualda, C., Moreno-Villaécija, M.A., et al., Chem. Eur. J., 2019, vol. 25, no. 53, p. 12367. https://doi.org/10.1002/chem.201901914
Petrikevich, D.K., Timoshchuk, V.A., Shadyro, O.I., et al., Pharm. Chem. J., 1995, vol. 29, no. 12, p. 32. https://doi.org/10.1007/BF02334494
Maslovskaya, L.A., Petrikevich, D.K., Timoshchuk, V.A., et al., Russ. J. Gen. Chem., 1996, vol. 66, no 11, p. 1847.
Smolyaninov, I., Pitikova, O., Korchagina, E., et al., Monatsh. Chem., 2018, vol. 149, p. 1813. https://doi.org/10.1007/s00706-018-2264-1
Smolyaninov, I.V., Berberova, N.T., Pitikova, O.V., et al., Russ. Chem. Bull., 2018, vol. 67, no. 10, p. 1857. https://doi.org/10.1007/s11172-018-2299-9
Ukhin, L.Y., Alexeenko, D.V., Belousova, L.V., et al., Russ. Chem. Bull., 2019, vol. 68, no. 12, p. 2290. https://doi.org/10.1007/s11172-019-2702-1
Musiejuk, M. and Witt, D., Org. Prep. Proced. Int., 2015, vol. 47, no. 2, p. 95. https://doi.org/10.1080/00304948.2015.1005981
Pires, M.M. and Chmielewski, J., Org. Lett., 2008, vol. 10, p. 837. https://doi.org/10.1021/ol702769n
Mayer, Ch.D., Allmendinger, L., and Bracher F., Tetrahedron, 2012, vol. 68, p. 1810. https://doi.org/10.1016/j.tet.2011.11.076
McCullocha, M.W.B., Coombs, G.S., Banerjee, N., et al., Bioorg. Med. Chem., 2009, vol. 17, p. 2189. https://doi.org/10.1016/j.bmc.2008.10.077
Liu, Ch., Pan, J., Li, Sh., et al., Angew. Chem. Int. Ed., 2011, vol. 50, p. 10327. https://doi.org/10.1002/ange.201104305
Houseman, B.T., Gawalt, E.S., and Mrksich, M., Langmuir, 2003, vol. 19, p. 1522. https://doi.org/10.1021/la0262304
Uragami, M., Miyake, Y., Tokutake, N., et al., Langmuir, 2000, vol. 16, p. 8010. https://doi.org/10.1021/la001065i
Diaz, C., Balasubramanian, K., and Schroit, A., J. Bioconjugate Chem., 1998, vol. 9, p. 250. https://doi.org/10.1021/bc970156x
El Alaoui, A., Schmidt, F., Amessou, M., et al., Angew. Chem. Int. Ed., 2007, vol. 46, p. 6469. https://doi.org/10.1002/ange.200701270
Asanuma, H., Kanemoto, K., Watanabe, T., et al., Angew. Chem. Int. Ed., 2023, vol. 62, no. 18, p. e202219156. https://doi.org/10.1002/anie.202219156
Tang, S. Liu, Y., and Lei, A., Chem, 2018, vol. 4, p. 27. https://doi.org/10.1016/j.chempr.2017.10.001
Tang, S., Zeng, L., and Lei, A., J. Am. Chem. Soc., 2018, vol. 140, p. 13128. https://doi.org/10.1021/jacs.8b07327
Jiang, Y., Xu, K., and Zeng, C., Chem. Rev., 2018, vol. 118, no. 9, p. 4485. https://doi.org/10.1021/acs.chemrev.7b00271
Baker, L.A., J. Am. Chem. Soc., 2018, vol. 140, no. 46, p. 15549. https://doi.org/10.1021/jacs.8b09747
Yuan, Y., Yu, Y., Qiao, J., et al., Chem. Comm., 2018, vol. 54, p. 11471. https://doi.org/10.1039/C8CC06451B
Wang, Y., Deng, L., Mei, H., et al., Green Chem., 2018, vol. 20, p. 3444. https://doi.org/10.1039/C8GC01337C
Romero, N.A. and Nicewicz, D.A., Chem. Rev., 2016, vol. 116, no. 17, p. 10075. https://doi.org/10.1021/acs.chemrev.6b00057
Jones, A.C., Leitch, J.A., Raby-Buck, S.E., et al., Nat. Synth., 2022, vol. 1, p. 763. https://doi.org/10.1038/s44160-022-00106-4
Chatterjee, T. and Ranu, B.C., J. Org. Chem., 2021, vol. 86, no. 20, p. 13895. https://doi.org/10.1021/acs.joc.1c01454
Do, Q.T., Elothmani, D., Le Guillanton, G., et al., Tetrahedron Lett., 1997, vol. 38, p. 3383. https://doi.org/10.1016/S0040-4039(97)00624-2
Matsumoto, K., Fujie, S., Suga, S., et al., Chem. Comm., 2009, vol. 36, p. 5448. https://doi.org/10.1039/B910821A
Matsumoto, K., Suga, S., and Yoshida, J., Org. Biomol. Chem., 2011, vol. 9, p. 2586. https://doi.org/10.1039/C0OB01070G
Lam, K. and Geiger, W.E., J. Org. Chem., 2013, vol. 78, no. 16, p. 8020. https://doi.org/10.1021/jo401263z
Huang, P., Wang, P., Tang, S., et al., Angew. Chem. Int. Ed., 2018, vol. 57, no. 27, p. 8115. https://doi.org/10.1002/ange.201803464
Li, Y., Wang, H., Wang, Z., et al., Chem. Sci., 2023, vol. 14, p. 372. https://doi.org/10.1039/D2SC05507D
Sattler, L.E., Otten, C.J., and Hilt, G., Chem. Eur. J., 2020, vol. 26, p. 3129. https://doi.org/10.1002/chem.201904948
Shinkar’, E.V., Shvetsova, A.V., Sediki, D.B., et al., Russ. J. Electrochem., 2015, vol. 51, no. 11, p. 1046. https://doi.org/10.1134/S1023193515110178
Berberova, N.T., Shinkar’, E.V., Smolyaninov, I.V., et al., Russ. J. Gen. Chem., 2015, vol. 85, no. 4, p. 998. https://doi.org/10.1134/S1070363215040416
Berberova, N.T., Smolyaninov, I.V., Shinkar, E.V., et al., Russ. Chem. Bull., 2018, vol. 67, no. 1, p. 108. https://doi.org/10.1007/s11172-018-2044-4
Shinkar’, E.V., Shvetsova, A.V., Okhlobystin, A.O., et al., Russ. J. Electrochem., 2020, vol. 56, no. 4, p. 285. https://doi.org/10.1134/S1023193520040138
Park, C.-M., Johnson, B.A., Duan, J., et al., Org. Lett., 2016, vol. 18, p. 904. https://doi.org/10.1021/acs.orglett.5b03557
Xiao, X., Feng, M., and Jiang, X., Angew. Chem. Int. Ed., 2016, vol. 55, p. 14121. https://doi.org/10.1002/anie.201608011
Wang, W., Org. Lett., 2018, vol. 20, p. 3829. https://doi.org/10.1021/acs.orglett.8b01418
Burmistrova, D.A., Smolyaninov, I.V., and Berberova, N.T., Russ. J. Electrochem., 2020, vol. 56, no. 4, p. 329. https://doi.org/10.1134/S1023193520040035
Francke, R. and Little, R.D., Chem. Soc. Rev., 2014, vol. 43, p. 2492. https://doi.org/10.1039/C3CS60464K
Francke, R. and Little, R.D., ChemElectroChem, 2019, vol. 6, p. 4373. https://doi.org/10.1002/celc.201900432
Ogibin, Yu.N., Elinson, M.N., and Nikishin, G.I., Russ. Chem. Rev., 2009, vol. 78, no. 2, p. 89. https://doi.org/10.1070/RC2009v078n02ABEH003886
Steckhan, E., Top. Curr. Chem., 1987, vol. 142, p. 1325. https://doi.org/10.1007/3-540-17871-6_11
Steckhan, E., Angew. Chem. Int. Ed., 1986, vol. 25, p. 683. https://doi.org/10.1002/anie.198606831
Fuchigami, T., Tetsu, M., Tajima, T., et al., Synlett., 2001, vol. 8, p. 1269. https://doi.org/10.1055/s-2001-16063
Shen, Y., Hattori, H., and Ding, K., Electrochim. Acta, 2006, vol. 51, p. 2819. https://doi.org/10.1016/j.electacta.2005.08.014
Masui, M. Recent Advances in Electroorganic Synthesis, New York: Marcel Dekker. 1989, p. 137.
Semmelhack, M.F., Chou, C.S., and Cortes, D.A., J. Am. Chem. Soc., 1983, vol. 105, no. 13, p. 4492. https://doi.org/10.1021/ja00351a070
Semmelhack, M.F. and Schmid, C.R., J. Am. Chem. Soc., 1983, vol. 105, no. 13, p. 6732. https://doi.org/10.1021/ja00360a042
Chiba, K., Arakawa, T., and Tada, M., J. Chem. Soc., Perkin Trans., 1998, vol. 1, p. 2939. https://doi.org/10.1039/A802306I
Utley, J.H.P. and Rozenberg, G.G., Tetrahedron, 2002, vol. 58, p. 5251. https://doi.org/10.1016/S0040-4020(02)00495-7
Utley, J.H.P. and Rozenberg, G.G., J. Appl. Electrochem., 2003, vol. 33, p. 525. https://doi.org/10.1023/A:1024474620525
Magdesieva, T.V. and Butin, K.P., Russ. Chem. Rev., 2002, vol. 71, p. 223. https://doi.org/10.1070/RC2002v071n03ABEH000704
Budnikova, Y.G. and Budnikov, G.K., Zh. Obshch. Khim., 1995, vol. 65, no. 9, p. 1517.
Vereshchagin, A.N., Elinson, M.N., Dorofeeva, E.O., et al., Tetrahedron, 2013, vol. 69, p. 5234. https://doi.org/10.1016/j.tet.2013.04.035
Elinson, M., Vereshchagin, A.N., and Tretyakova, E.O., Synthesis, 2011, vol. 18, p. 3015. https://doi.org/10.1055/s-0030-1261031
Baba, D. and Fuchigami, T., Tetrahedron Lett., 2003, vol. 44, no. 28, p. 3133. https://doi.org/10.1016/S0040-4039(03)00548-3
Sun, X.-J., Yang, S.-F., and Wang, Z.-T., ChemistrySelect, 2020, vol. 5, p. 4637. https://doi.org/10.1002/slct.202000872
Kudryavtcev, D.A., Shinkar’, E.V., and Berberova, N.T., Geol. Geo. Glob. Energy, 2014, vol. 3, no. 54, p. 123.
Shinkar’, E.V., Okhlobystin, A.O., Berberova, N.T., et al., Russ. J. Gen. Chem., 2012, vol. 82, no. 5, p. 815. https://doi.org/10.1134/S1070363212050015
Berberova, N.T., Smolyaninov, I.V., Shinkar, E.V., et al., Int. J. Electrochem. Sci., 2019, vol. 14, p. 531. https://doi.org/10.20964/2019.01.15
Berberova, N.T., Shinkar’, E.V., Smolyaninov, I.V., et al., Dokl. Chem., 2015, vol. 465, no. 2, p. 295. https://doi.org/10.1134/S0012500815120058
Okhlobystin, A.O., Okhlobystina, A.V., Shinkar’, E.V., et al., Dokl. Chem., 2010, vol. 435, no. 1, p. 302. https://doi.org/10.1134/S001250081011008X
Okhlobystin, A.O., Smolyaninov, I.V., Okhlobystina, A.V., et al., Russ. J. Coord. Chem., 2013, vol. 39, no. 1, p. 33. https://doi.org/10.1134/S1070328413010077
Lavrent’ev, V.A., Shinkar’, E.V., Smolyaninov, I.V., et al., Russ. J. Coord. Chem., 2021, vol. 47, p. 341. https://doi.org/10.1134/S1070328421050031
Burmistrova, D.A., Smolyaninov, I.V., Berberova, N.T., et al., ChemistrySelect, 2020, vol. 5, no. 45, p. 14515. https://doi.org/10.1002/slct.202003961
Burmistrova, D.A., Galustyan, A., Smolyaninov, I.V., et al., J. Electrochem. Soc., 2021, vol. 168, no. 5, p. 055501. https://doi.org/10.1149/1945-7111/abfe43
Burmistrova, D.A., Galustyan, A., Smolyaninov, I.V., et al., J. Electrochem. Soc., 2022, vol. 169, no. 11, p. 116501. https://doi.org/10.1149/1945-7111/ac9d69
Ghammamy, S. and Tajbakhsh, M., J. Sulfur Chem., 2005, vol. 26, p. 145. https://doi.org/10.1080/17415990500089086
Botteselle, G.V., Godoi, M., Galetto, F.Z., et al., J. Mol. Cat. A, 2012, vol. 365, p. 186. https://doi.org/10.1016/j.molcata.2012.09.003
Wang, J.-X., Gao, L., and Huang, D., Synth. Comm., 2002, vol. 32, p. 963. https://doi.org/10.1081/SCC-120003143
Cabrera, D.M.L., Líbero, F.M., Alves, D., et al., Green Chem. Lett. Rev., 2012, vol. 5, p. 329. https://doi.org/10.1080/17518253.2011.631942
Kutuk, H. and Turkoz, N., Phosphorus, Sulfur Relat. Elem., 2010, vol. 186, p. 1515. https://doi.org/10.1080/10426507.2010.520174
Karakullukcu, N.T., Yakan, H., Ozturk, S., et al., Phosphorus, Sulfur Relat. Elem., 2013, vol. 188, p. 1576. https://doi.org/10.1080/10426507.2013.769984
Lu, X., Wang, H., Gao, R., et al., RSC Adv., 2014, vol. 4, p. 28794. https://doi.org/10.1039/C4RA03592E
Lenardão, E.J., Lara, R.G., Silva, M.S., et al., Tetrahedron Lett., 2007, vol. 48, p. 7668. https://doi.org/10.1016/j.tetlet.2007.08.094
Bottecchia, C., Erdmann, N., Tijssen, P.M.A., et al., ChemSusChem, 2016, vol. 9, p. 1781. https://doi.org/10.1002/cssc.201600602
Xu, H., Shi, J.-L., Lyu, S., et al., Chin. J. Catal., 2020, vol. 41, p. 1468. https://doi.org/10.1016/S1872-2067(20)63640-3
Talla, A., Driessen, B., and Straathof, N.J.W., Adv. Synth. Catal., 2015, vol. 357, p. 2180. https://doi.org/10.1002/adsc.201401010
Oka, M., Katsube, D., Tsuji, T., et al., Org. Lett., 2020, vol. 22, no. 23, p. 9244.https://doi.org/10.1021/acs.orglett.0c03458
Xu, H., Zhang, Y.-F., and Lang, X., Chin. Chem. Lett., 2020, vol. 31, p. 1520. https://doi.org/10.1016/j.cclet.2019.10.024
Spiliopoulou, N. and Kokotos, C.G., Green Chem., 2021, vol. 23, p. 546. https://doi.org/10.1039/D0GC03818K
Ren, M.-Z., Fu, Y.-J., Zhang, B.-S., et al., Synthesis, 2023, vol. 55, no. 13, p. 2011. https://doi.org/10.1055/s-0042-1751433
Dethe, D.H., Srivastava, A., Dherange., B.D., et al., Adv. Synth. Catal., vol. 360, no. 16, p. 3020. https://doi.org/10.1002/adsc.201800405
Funding
The first section of the review (Metal-Containing Catalysts in the Synthesis of Disulfides) was written with the support of the Council on Grants of the President of the Russian Federation for the state support of young scientist-candidates of science (grant no. MK-2488.2022.1.3) and writing of other sections was supported by the Russian Science Foundation (project no. 23-13-00201).
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Burmistrova, D.A., Smolyaninov, I.V. & Berberova, N.T. Modern Trends in the Synthesis of Disulfides: From Metal-Containing Catalysts to Nonmaterial Reagents (Review). Russ J Coord Chem 49 (Suppl 2), S159–S195 (2023). https://doi.org/10.1134/S1070328423600985
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DOI: https://doi.org/10.1134/S1070328423600985