Механохимический синтез галогенорганических соединений: взгляд синтетика
- Авторы: Бородкин Г.И.1
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Учреждения:
- Новосибирский институт органической химии им. Н. Н. Ворожцова СО РАН
- Выпуск: Том 92, № 9 (2023)
- Страницы: RCR5091
- Раздел: Статьи
- URL: https://journals.rcsi.science/0042-1308/article/view/252026
- DOI: https://doi.org/10.59761/RCR5091
- ID: 252026
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Аннотация
Обобщены литературные сведения по механохимическому синтезу галогенсодержащих органических соединений, полученные преимущественно за последние 10 лет. Обсуждены сложившиеся представления о методах активации механохимических реакций галоидирования органических соединений. Рассмотрены механохимические реакции фторирования, хлорирования, бромирования и иодирования. Особое внимание уделено механизмам реакций, проблеме селективности и рассмотрению механохимического метода как одного из перспективных направлений развития "зеленой химии". Обзор посвящен применению механохимии в органическом синтезе и не рассматривает фундаментальные основы механохимии.Библиография — 155 ссылок.
Об авторах
Геннадий Иванович Бородкин
Новосибирский институт органической химии им. Н. Н. Ворожцова СО РАН
Email: gibor@nioch.nsc.ru
доктор химических наук, профессор
Список литературы
- Fluorine in Medicinal Chemistry and Chemical Biology. (Ed. I.Ojima). (Chichester: Wiley, 2009)
- J.S.Walsh, G.T.Miwa. Annu. Rev. Pharmacol. Toxicol., 51, 145 (2011)
- H.Mei, J.Han, S.White, D.J.Graham, K.Izawa, T.Sato, S.Fustero, N.A.Meanwell, V.A.Soloshonok. Chem. – Eur. J., 26, 11349 (2020)
- Y.Zhou, J.Wang, Z.Gu, S.Wang, W.Zhu, J.L.Aceña, V.F.Soloshonok, K.Izawa, H.Liu. Chem. Rev., 116, 422 (2016)
- J.Wang, M.Sánchez-Roselló, J.L.Aceña, C.del Pozo, A.E.Sorochinsky, S.Fustero, V.A.Soloshonok, H.Liu. Chem. Rev., 114, 2432 (2014)
- P.Dhiman, N.Arora, P.V.Thanikachalam, V.Monga. Bioorg. Chem., 92, 103291 (2019)
- E.V.Nosova, G.N.Lipunova, V.N.Charushin, O.N.Chupakhin. J. Fluor. Chem., 131, 1267 (2010)
- P.Ferraboschi, S.Ciceri, P.Grisenti. Org. Prep. Proc. Int., 49, 69 (2017)
- P.K.Mykhailiuk. Chem. Rev., 121, 1670 (2021)
- P.A.Zaikin, G.I.Borodkin. In Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates. (Ed. Al Postigo). (Amsterdam: Elsevier, 2019). Р.105
- Y.Ma, E.Frutos-Beltrán, D.Kang, C.Pannecouque, E.De Clercq, E.L.Menéndez-Arias, X.Liu, P.Zhan. Chem. Soc. Rev., 50, 4514 (2021)
- D.B.Tiz, L.Bagnoli, O.Rosati, F.Marini, L.Sancineto, C.Santi. Molecules, 27, 1643 (2022)
- D.A.McNaughton, M.Fares, G.Picci, P.A.Gale, C.Caltagirone. Coord. Chem. Rev., 427, 213573 (2021)
- J.Jia, L.Wu. Tetrahedron Lett., 61, 152486 (2020)
- R.Kampes, S.Zechel, M.D.Hager, U.S.Schubert. Chem. Sci., 12, 9275 (2021)
- F.Li, M.Wang, S.Liu, Q.Zhao. Chem. Sci., 13, 2184 (2022)
- P.Jeschke. Eur. J. Org. Chem., e202101513 (2022)
- M.Kamigaito, Polymer J., 54, 1391 (2022)
- L.Martinelli, P.I.Nikel. Microbiol. Biotechnol., 12, 187 (2019)
- M.Kleoff, P.Voßnacker, S.Riedel. Angew. Chem., Int. Ed., 62, e202216586 (2023)
- M.D.Mashkovskii. Lekarstvennye Sredstva. (Medicines). Vols. 1, 2. (Mosxow: Novaya Volna, 2002)
- F.Salas-Lucia, A.C.Bianco. Front. Endocrinol., 13, 1, 1044691 (2022)
- D.Corinti, B.Chiavarino, M.Spano, A.Tintaru, S.Fornarini, M.E.Crestoni. Anal. Chem., 93, 14869 (2021)
- S.Mondal, G.Mugesh. Angew. Chem., Int. Ed., 54, 10833 (2015)
- A.Cros, G.Alfaro-Espinoza, A.De Maria, N.T.Wirth, P.I.Nikel. Current Opin. Biotechn., 74, 180 (2022)
- P.Shah, A.D.Westwell. J. Enzyme Inhibit. Med. Chem., 22, 527 (2007)
- D.Gimenez, C.A.Mooney, A.Dose, G.Graham Sandford, C.R.Coxon, S.L.Cobb. Org. Biomol. Chem., 15, 4086 (2017)
- A.S.Hudson, A.Hoose, C.R.Coxon, G.Sandford, S.L.Cobb. Tetrahedron Lett., 54, 4865 (2013)
- P.T.Lowe, D.O’Hagan. Chem. Soc. Rev., 52, 248 (2023)
- C.Varlow, D.Szames, K.Dahl, V.Bernard-Gauthierac, N.Vasdev. Chem. Commun., 54, 11835 (2018)
- C.Zhang, K.Yan, C.Fu, H.Peng, C.J.Hawker, A.K.Whittaker. Chem. Rev., 122, 167 (2022)
- S.Preshlock, M.Tredwell, V.Gouverneur. Chem. Rev., 116, 719 (2016)
- W.Lorpaiboon, P.Bovonsombat. Org. Biomol. Chem., 19, 7518 (2021)
- A.Varenikov, E.Shapiro, M.Gandelman. Chem. Rev., 121, 412 (2021)
- L.A.Segura-Quezada, K.R.Torres-Carbajal1, Y.Satkar, K.A.Juárez Ornelas,N.Mali, D.B.Patil, R.Gámez-Montaño, J.R.Zapata-Morales, S.Lagunas-Rivera, R.Ortíz-Alvarado, C.R.Solorio-Alvarado. Mini-Reviews Org. Chem., 18, 15 (2021)
- G.I.Borodkin, V.G.Shubin. Russ. Chem. Rev., 88, 160 (2019)
- L.Zhang, T.Ritter. J. Am. Chem. Soc., 144, 2399 (2022)
- B.-Y.Qian, W.Zhang, J.-H.Lin, W.Cao, J.-C.Xiao. Chem. – Asian J., 17, e202200184 (2022)
- K.Jakhar. Curr. Org. Synth., 19, 849 (2022)
- M.E.Hirschberg, N.V.Ignat’ev, A.Wenda, H.Willner. J. Fluor. Chem., 137, 50 (2012)
- Y.-H.Oh, D.W.Kim, S.Lee. Molecules, 27, 5702 (2022)
- G.I.Borodkin, V.G.Shubin. Russ. J. Org. Chem., 42, 1745 (2006)
- G.I.Borodkin, V.G.Shubin. Chem. Heterocyclic Comp., 58, 84 (2022)
- G.I.Borodkin, I.R.Elanov, V.G.Shubin. ARKIVOC, part ii, 60 (2018)
- G.I.Borodkin, I.R.Elanov, Y.V.Gatilov, V.G.Shubin. J. Fluor. Chem., 228, 109412 (2019)
- L.Yang, T.Dong, H.M.Revankar, C.-P.Zhang. Green Chem., 19, 3 (2017)
- J.B.Manley. In Scalable Green Chemistry: Case Studies from the Pharmaceutical Industry. (Ed. S.G.Koenig). (Stanford: Taylor & Francis Group, 2013). P. 1
- H.C.Erythropel, J.B.Zimmerman, T.M.de Winter, L.Petitjean, F.Melnikov, C.H.Lam, A.W.Lounsbury, K.E.Mellor, N.Z.Janković, Q.Tu, L.N.Pincus, M.M.Falinski, W.Shi, W.P.Coish, D.L.Plata, P.T.Anastas. Green Chem., 20, 1929 (2018)
- K.J.Ardila-Fierro, J.G.Hernández. ChemSusChem, 14, 2145 (2021)
- R.A.Sheldon. Pure Appl. Chem., 72, 1233 (2000)
- F.Gomollón-Bel. Chem. Int., 41, 12 (2019)
- M.Leonardi, M.Villacampa, J.C.Menéndez. Chem. Sci., 9, 2042 (2018)
- T.H.El-Sayed, A.Aboelnaga, M.A.El-Atawy, M.Hagar. Molecules, 23, 1348 (2018)
- T.K.Achar, A.Bose, P.Mal. Beilstein J. Org. Chem., 13, 1907 (2017)
- S.Zhao, Y.Li, C.Liu, Y.Zhao. Tetrahedron Lett., 59, 317 (2018)
- B.C.Ranu, T.Ghosh, S.Jalal. ARKIVOC, part iii, 79 (2019)
- I.N.Egorov, S.Santra, D.S.Kopchuk, I.S.Kovalev, G.V.Zyryanov, A.Majee, B.C.Ranu, V.L.Rusinov, O.N.Chupakhin. Green Chem., 22, 302 (2020)
- M.T.J.Williams, L.C.Morrill, D.L.Browne. ChemSusChem, 15, e202102157 (2022)
- V.Štrukil. Synlett, 29, 1281 (2018)
- T.Friščić, C.Mottillo, H.M.Titi. Angew. Chem., Int. Ed., 59, 1018 (2020)
- R.T.O’Neill, R.Boulatov. Nature Rev. Chem., 5, 148 (2021)
- P.Ying, J.Yu, W.Su. Adv. Synth. Catal., 363, 1246 (2021)
- Z.Kun, M.Yangjie, W.Fengwei, L.Shaojie, X.Danqian. Chin. J. Org. Chem., 41, 4623 (2021)
- S.Gupta, J.M.Khurana. Green Chem., 19, 4153 (2017)
- F.Puccetti, C.Schumacher, H.Wotruba, J.G.Hernández, C.Bolm. ACS Sust. Chem. Eng., 8, 7262 (2020)
- T.Seo, K.Kubota, H.Ito. J. Am. Chem. Soc., 142, 9884 (2020)
- S.Panja, B.Paul, S.Jalal, T.Ghosh, B.C.Ranu. ChemistrySelect 5, 14198 (2020)
- J.-H.Schöbel, W.Liang, D.Wöll, C.Bolm. J. Org. Chem., 85, 15760 (2020); https://dx.doi.org/10.1021/acs.joc.0c02599
- J.-H.Schöbel, P.Elbers, K.-N.Truong, K.Rissanen, C.Bolm. Adv. Synth. Catal., 363, 1322 (2021)
- V.C.Basappa, S.Penubolu, D.K.Achutha, A.Kariyappa. J. Chem. Sci., 133, 55 (2021)
- S.Mkrtchyan, M.Jakubczyk, S.Lanka, M.Yar, K.Ayub, M.Shkoor, M.Pittelkow, V.O.Iaroshenko. Adv. Synth. Catal., 363, 5448 (2021)
- A.Zulfiqar, D.Ahmed. Asian J. Green Chem., 6, 40 (2022)
- D.Bhattacherjee, I.S.Kovalev, D.S.Kopchuk, M.Rahman, S.Santra, G.V.Zyryanov, P.Das, R.Purohit, V.L.Rusinov, O.N.Chupakhin. Molecules, 27, 7784 (2022)
- F.Casti, R.Mocci, A.Porcheddu. Beilstein J. Org. Chem., 18, 1210 (2022)
- G.Mlostoń, M.Celeda, H.Heimgartner, D.Duda, E.Obijalska, M.Jasiński. Catalysts, 12, 589 (2022)
- K.Ciesielska, M.Hoffmann, M.Kubicki, D.Pluskota-Karwatka. Molecules, 27, 4557 (2022)
- M.Molnar, M.Komar, I.Jerković. Molbank, 2022, M1500 (2022)
- I.N.Egorov, A.Mukherjee, S.Santra, D.S.Kopchuk, I.S.Kovalev, Y.Liu, G.V.Zyryanov, A.Majee, O.N.Chupakhin, B.C.Ranue. Adv. Synth. Catal., 364, 2462 (2022)
- L.Li, C.Niu, G.-W.Wang. Chin. J. Chem., 40, 2539 (2022)
- L.Takacs. Chem. Soc. Rev., 42, 7649 (2013)
- C.Xu, S.De, A.M.Balu, M.Ojeda, R.Luque. Chem. Commun., 51, 6698 (2015)
- G.Scholz. ChemTexts, 7,16 (2021)
- S.Hwang, S.Grätz, L.Borchardt. Chem. Commun., 58, 1661 (2022)
- M.Pérez-Venegas, E.Juaristi. ACS Sustainable Chem. Eng., 8, 8881 (2020)
- C.G.Avila-Ortiz, E.Juaristi. Molecules, 25, 3579 (2020)
- E.C.Gaudino, G.Grillo, M.Manzoli, S.Tabasso, S.Maccagnan, G.Cravotto. Molecules, 27, 449 (2022)
- O.Bento, F.Luttringer, T.M.El Dine, N.Petry, X.Bantreil, F.Lamaty. Eur. J. Org. Chem., e202101516 (2022)
- I.Priestley, C.Battilocchio, A.V.Iosub, F.Barreteau, G.W.Bluck, K.B.Ling, K.Ingram, M.Ciaccia, J.A.Leitch, D.L.Browne. Org. Process Res. Dev., 27, 269 (2023)
- J.L.Howard, Q.Cao, D.L.Brown. Chem. Sci., 9, 3080 (2018)
- D.Margetić, V.Štrukil. In Organic Synthesis – A Nascent Relooks. (Ed. B.P.Nandeshwarappa). (London: Books on Demand, 2020). P. 27
- G.I.Borodkin, V.G.Shubin. Russ. J. Org. Chem., 57, 1369 (2021)
- S.Zangade, P.Patil, Curr. Org. Chem., 23, 2295 (2019)
- D.Y.Bae, E.Lee. J. Radiopharm Mol. Prob., 4, 11 (2018)
- G.I.Borodkin, V.G.Shubin. Russ. Chem. Rev., 79, 259 (2010)
- C.B.McPake, G.Sandford. Org. Process Res. Dev., 16, 844 (2012)
- C.A.Ramsden. ARKIVOC, part i, 109 (2014)
- K.Yang, M.Song, A.I.M.Ali, S.M.Mudassir, H.Ge. Chem. – Asian J., 15, 729 (2020)
- T.Umemoto, Y.Yang, G.B.Hammond. Beilstein J. Org. Chem., 17, 1752 (2021)
- F.-L.Qing, X.-Y.Liu, J.-A.Ma, Q.Shen, Q.Song, P.Tang. CCS Chem., 4, 2518 (2022)
- J.L.Howard, Y.Sagatov, L.Repusseau, C.Schotten, D.L.Browne. Green Chem., 19, 2798 (2017)
- R.R.A.Bolt, J.A.Leitch, A.C.Jones, W.I.Nicholson. D.L.Browne. Chem. Soc. Rev., 51, 4243 (2022)
- Q.Cao, J.L.Howard, D.E.Crawford, S.L.James, D.L.Browne. Green Chem., 20, 4443 (2018)
- J.L.Howard, Y.Sagatov, D.L.Browne. Tetrahedron, 74, 3118 (2018)
- Y.Wang, H.Wang, Y.Jiang, C.Zhang, J.Shao, D.Xu. Green. Chem., 19, 1674 (2017)
- J.L.Howard, W.Nicholson, Y.Sagatov, D.L.Browne. Beilstein J. Org. Chem., 13, 1950 (2017)
- P.A.Zaikin, O.T.Dyan, I.R.Elanov, G.I.Borodkin. Molecules, 26, 5756 (2021)
- G.Tarantino, L.Botti, N.Dimitratos, C.Hammond. RSC Adv., 7, 30185 (2017)
- S.Min, B.Park, J.Nedsaengtip, S.H.Hong. Adv. Synth. Catal., 364, 1975 (2022)
- J.G.Hernández, K.J.Ardila-Fierro, D.Barišić, H.Geneste. Beilstein J. Org. Chem., 18, 182 (2022)
- P.A.Zaikin, O.T.Dyan, D.V.Evtushok, A.N.Usoltsev, G.I.Borodkin, E.V.Karpova, V.G.Shubin. Eur. J. Org. Chem., 2469(2017)
- G.Borodkin, I.Elanov, V.Shubin. In Sbornik Tezisov Dokladov na Vserossiiskoi Konferentsii s Mezhdunarodnym Uchastiem ‘Sovremeennye Problemy Organicheskoi Khimii’. (Collection of Abstracts of Reports at the All-Russian Conference with International Participation ‘Modern Problems of Organic Chemistry’). (Novosibirsk, 2021). P. 71
- D.Krištofíková, M.Mečiarová, E.Rakovský, R.Šebesta. ACS Sustainable Chem. Eng., 38, 14417 (2020)
- W.Riley, A.C.Jones, K.Singh, D.L.Browne, A.M.Stuart. Chem. Commun., 57, 7406 (2021)
- A.K.Mishra, H.Nagarajaiah, J.N.Moorthy. Eur. J. Org. Chem., 2733 (2015)
- I.Neogi, P.J.Das, F.Grynszpan. Synlett, 29, 1043 (2018)
- H.Nagarajaiah, A.K.Mishra, J.N.Moorthy. Org. Biomol. Chem., 14, 4129 (2016)
- M.Bilke, P.Losch, O.Vozniuk, A.Bodach, F.Schüth. J. Am. Chem. Soc., 141, 11212 (2019)
- Patent EP 3705467A1 (2020)
- R.Schmidt, A.Stolle, B.Ondruschka. Green Chem., 14, 1673 (2012)
- A.Bose, P.Mal. Tetrahedron Lett., 55, 2154 (2014)
- D.Das, A.A.Bhosle, A.Chatterjee, M.Banerjee. Beilstein J. Org. Chem., 18, 999 (2022)
- D.Barišić, M.Pajić, I.Halasz, D.Babić, M.Ćurić. Beilstein J. Org. Chem., 18, 680 (2022)
- S.K.Bera, P.Mal. J. Org. Chem., 86, 14144 (2021)
- D.R.Indukuri, G.R.Potuganti, M.Alla. Synlett, 30, 1573 (2019)
- J.Višňovský, P.Billik, R.Kubinec, P.Podolec, A.H.Szabó, M.Juriga, R.Čabala, J.Kubincová, J.Blaško. Tetrahedron Lett., 54, 7180,(2013)
- J.-X.Chen, Y.-T.Wang, C.-M.Chen, C.T.To. J. Chin. Chem. Soc., 1 (2023)
- I.C.B.Martin, M.Carta, S.Haferkamp, T.Feiler, F.Delogu, E.Colacin, F.Emmerling. ACS Sustainable Chem. Eng., 9, 37, 12591 (2021)
- S.Terhorst, T.Jansen, T.Langletz, C.Bolm. Org. Lett., 24, 4109 (2022)
- G.-W.Wang, J.Gao. Green Chem., 14, 1125 (2012)
- N.N.Pesyan, A.Gharib, A.Monfaredd, S.Azizid, H.Sanaee. Iran. Chem. Commun., 7, 251 (2019)
- K.J.Ardila-Fierro, L.Vugrin, I.Halasz, A.Palčić, J.G.Hernandez. Chem. – Methods, 2, e202200035 (2022)
- D.Barišić, I.Halasz, A.Bjelopetrović, D.Babić, M.Ćurić. Organometallics, 41, 1284, (2022)
- E.Bartalucci, C.Schumacher, L.Hendrickx, F.Puccetti, I.d’Anciães Almeida Silva, R.Dervişoğlu, R.Puttreddy, C.Bolm, T.Wiegand. Chem. – Eur. J., e202203466 (2023)
- J.G.Hernández, С.Bolm. Chem. Commun., 51, 12582 (2015)
- A.Bal, T.K.Dinda, P.Mal. Asian J. Org. Chem., 11, e202200046 (2022)
- J.Wong, Y.-Y.Yeung. RSC Adv., 11, 13564 (2021)
- S.Maitia, P.Mal. Synth. Commun., 44, 3461 (2014)
- G.Sereda, A.M.Sarkar, A.Hussain, N.Zefirov. Synthesis, 52, 1140 (2020)
- Z.Liu, H.Xu, G.-W.Wang. Beilstein J. Org. Chem., 14, 430 (2018)
- A.C.Mantovani, J.G.Hernandez, C.Bolm. Eur. J. Org. Chem., 2458 (2018)
- A.Halder, D.Maiti, S.D.Sarkar. Chem. – Asian J., 15, 577 (2020)
- E.Kolvari, A.Amoozadeh, N.Koukabi, S.Otokesh, M.Isari. Tetrahedron Lett., 55, 3648 (2014)
- V.Martinez, T.Stolar, B.Karadeniz, I.Brekalo, K.Užarević. Nature Rev. Chem., 7, 51 (2023)
- X.Liu, Y.Li, L.Zeng, X.Li, N.Chen, S.Bai, H.He, Q.Wang, C.Zhang. Adv. Mater., 34, 2108327 (2022)
- M.B.Gawande, V.D.B.Bonifácio, R.Luque, P.S.Branco, R.S.Varma. ChemSusChem, 7, 24 (2014)
- G.Cravotto, E.C.Gaudinoa, P.Cintas. Chem. Soc. Rev., 42, 7521 (2013)
- J.G.Hernández. Chem. – Eur. J., 23, 17157 (2017)
- T.Stauch, A.Dreuw. Acc. Chem. Res., 50, 1041 (2017)
- E.G.Avvakumov. Mekhanicheskie Metody Aktivatsii Khimicheskikh Protsessov. (Mechanical Methods for Activating Chemical Processes). (Moscow: Izd. LENAND, 2022)
- O.V.Lapshin, E.V.Boldyreva, V.V.Boldyrev. Russ. J. Inorg. Chem, 66, 433 (2021)
- O.V.Lapshin, V.V.Boldyrev, E.V.Boldyreva. Russ. J. Phys. Chem., 95, 2310 (2021)
- J.-L.Do, T.Friščić. Synlett, 28, 2066 (2017)
- K.D.M.Harris. Nature Chem., 5, 12 (2013); www.nature.com/naturechemistry
- B.S.Pladevall, A.de Aguirre, F.Maseras. ChemSusChem, 14, 2763 (2021)
- W.Quapp, J.M.Bofill. J. Comput. Chem., 37, 2467 (2016)