Palladium-Catalyzed Amination for the Synthesis of Macrocycles and Polymacrocycles: Contribution of Professor I.P. Beletskaya

  • Alexei D. Averin Московский государственный университет имени М.В. Ломоносова, Химический факультет
  • Anton S. Abel Московский государственный университет имени М.В. Ломоносова, Химический факультет
  • Anna S. Malysheva Московский государственный университет имени М.В. Ломоносова, Химический факультет
  • Nataliya M. Chernichenko Московский государственный университет имени М.В. Ломоносова, Химический факультет
  • Alexei A. Yakushev Московский государственный университет имени М.В. Ломоносова, Химический факультет
Ключевые слова: макроциклы, криптанды, полиамины, катализ комплексами палладия, аминирование, хиральность

Аннотация

Данный мини-обзор посвящен вкладу Академика РАН профессора И.П. Белецкой, руководителя Лаборатории элементоорганических соединений Химического факультета МГУ имени М.В. Ломоносова, в стратегию синтеза разнообразных макроциклических и полимакроциклических соединений с использованием реакции палладий-катализируемого аминирования. На протяжении более двух десятилетий эта химия планомерно и успешно развивается, начиная с достаточно простых соединений, переходя к более усложненным молекулам, содержащим несколько макроциклов, а относительно недавно начато исследование соединений, включающих в свой состав флуорофорные и хиральные структурные фрагменты для детектирования катионов металлов и хиральных органических молекул. В результате получены многие сотни соединений – в том числе производные диазакраун-эфиров и тетраазамакроциклов (циклен и циклам), структуры с эндоциклическими ароматическими и гетероароматическими фрагментами. Роль палладий-катализируемого аминирования – ключевого процесса в синтезе всего многообразия такого рода соединений – невозможно переоценить.

Литература

Ruiz-Castillo P., Buchwald S.L. Chem. Rev. 2016, 116, 12564-12649. https://doi.org/10.1021/acs.chemrev.6b00512

Heravi M.M., Kheilkordi Z., Zadsirjan V., Heydari M., Malmir M. J. Organomet. Chem. 2018, 861, 17-104. https://doi.org/10.1016/j.jorganchem.2018.02.023

Dorel R., Grugel C.P., Haydl A.M. Angew. Chem. Int. Ed. 2019, 58, 17118-17129. https://doi.org/10.1002/anie.201904795

Guram A.S., Rennels R.A., Buchwald S.L. Angew. Chem. Int. Ed. 1995, 34, 1348. https://doi.org/10.1002/anie.199513481

Louie J., Hartwig J.F. Tetrahedron Lett. 1995, 36, 3609-3612. https://doi.org/10.1016/0040-4039(95)00605-C

Yang B., Buchwald S.L. J. Organomet. Chem. 1999, 576, 125-146. https://doi.org/10.1016/S0022-328X(98)01054-7

Hartwig J.F. Angew. Chemie Int.Ed. 1998, 37, 2046-2067. https://doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L

Davydov D.V., Beletskaya I.P. Russ. Chem. Bull. 1995, 44, 1141-1141. https://doi.org/10.1007/BF00707076

Guilard R., Bessmertnykh A.G., Beletskaya I.P. Tetrahedron Lett. 1997, 38, 2287-2290. https://doi.org/10.1016/S0040-4039(97)00363-8

Beletskaya I.P., Bessmertnykh A.G., Guilard R. Synlett 1999, 1999, 1459-1461. https://doi.org/10.1055/s-1999-2837

Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L. J. Org. Chem. 2000, 65, 1158-1174. https://doi.org/10.1021/jo991699y

Beletskaya I.P., Bessmertnykh A.G., Averin A.D., Denat F., Guilard R. Eur. J. Org. Chem. 2005, 2005, 261-280. https://doi.org/10.1002/ejoc.200400456

Averin A.D., Shukhaev A.V., Buryak A.K., Beletskaya I.P. Russ. J. Org. Chem. 2009, 45, 1353-1364. https://doi.org/10.1134/S1070428009090085

Beletskaya I.P., Averin A.D., Borisenko A.A., Denat F., Guilard R. Tetrahedron Lett. 2003, 44, 1433-1435. https://doi.org/10.1016/S0040-4039(02)02841-1

Averin A.D., Shukhaev A.V., Golub S.L., Buryak A.K., Beletskaya I.P. Synthesis 2007, 2007, 2995-3012. https://doi.org/10.1055/s-2007-990779

Averin A.D., Uglov A.N., Buryak A.K., Beletskaya I.P. Mendeleev Commun. 2010, 20, 1-3. https://doi.org/10.1016/j.mencom.2010.01.001

Averin A.D., Uglov A.N., Buryak A.K., Beletskaya I.P. Macroheterocycles 2009, 2, 275-280. https://doi.org/10.6060/mhc2009.3-4.275

Averin A.D., Uglov A.N., Beletskaya I.P. Chem. Lett. 2008, 37, 1074-1075. https://doi.org/10.1246/cl.2008.1074

Beletskaya I.P., Averin A.D., Bessmertnykh A.G., Guilard R. Tetrahedron Lett. 2001, 42, 4983-4986. https://doi.org/10.1016/S0040-4039(01)00831-0

Beletskaya I.P., Averin A.D., Bessmertnykh A.G., Guilard R. Tetrahedron Lett. 2001, 42, 4987-4989. https://doi.org/10.1016/S0040-4039(01)00832-2

Beletskaya I.P., Bessmertnykh A.G., Averin A.D., Denat F., Guilard R. Eur. J. Org. Chem., 2005, 2005, 281-305. https://doi.org/10.1002/ejoc.200400456

Averin A.D., Ranyuk E.R., Buryak A.K., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P. Mendeleev Commun. 2009, 19, 136-138. https://doi.org/10.1016/j.mencom.2009.05.007

Ranyuk E.R., Averin A.D., Buryak A.K., Savel'ev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P. Russ. J. Org. Chem. 2009, 45, 1555-1566. https://doi.org/10.1134/S1070428009100236

Uglov A.N., Averin A.D., Buryak A.K., Beletskaya I.P. ARKIVOC, 2011, viii, 99-122. https://doi.org/10.3998/ark.5550190.0012.807

Uglov A.N., Averin A.D., Buryak A.K., Bessmertnykh Lemeune A., Guilard R., Beletskaya I.P. Macroheterocycles 2013, 6, 33-39. https://doi.org/10.6060/mhc121215a

Averin A.D., Ranyuk E.P., Buryak A.K., Beletskaya I.P. J. Org. Chem. 2008, 44, 1671-1685. https://doi.org/10.1134/S1070428008110195

Averin A.D., Ranyuk E.R., Buryak A.K., Beletskaya I.P. Chem. Lett. 2008, 37, 161-161. https://doi.org/10.1246/cl.2008.160

Beletskaya I.P., Averin A.D., Pleshkova N.A., Borisenko A.A., Serebryakova M.V., Denat F., Guilard R. Synlett 2005, 2005, 87-90. https://doi.org/10.1055/s-2004-836040

Averin A.D., Ulanovskaya O.A., Pleshkova N.A., Borisenko A.A., Beletskaya I.P. Collect. Czech. Chem. Commun. 2007, 72, 785-819. https://doi.org/10.1135/cccc20070785

Averin A.D., Ulanovskaya O.A., Borisenko A.A., Serebryakova M.V., Beletskaya I.P. Tetrahedron Lett. 2006, 47, 2691-2694. https://doi.org/10.1016/j.tetlet.2006.02.095

Beletskaya I.P., Averin A.D., Ulanovskaya O.A., Fedotenko I.A., Borisenko A.A., Serebryakova M.V., Denat F., Guilard R. Chem. Lett. 2005, 34, 1100-1101. https://doi.org/10.1246/cl.2005.1100

Averin A.D., Ulanovskaya O.A., Fedotenko I.A., Borisenko A.A., Serebryakova M.V., Beletskaya I.P., Helv. Chim. Acta 2005, 88, 1983-2002. https://doi.org/10.1002/hlca.200590152

Averin A.D., Uglov A.N., Buryak A.K., Bessmertnykh A.G., Guilard R., Beletskaya I.P. Heterocycles 2010, 80, 957-975. https://doi.org/10.3987/COM-09-S(S)68

Abel A.S., Averin A.D., Beletskaya I.P. New J. Chem. 2016, 40, 5818-5828. https://doi.org/10.1039/C5NJ03231H

Abel A.S., Mitrofanov A.Yu., Rousselin Y., Denat F., Bessmertnykh-Lemeune A., Averin A.D., Beletskaya I.P. ChemPlusChem 2016, 81, 35-39. https://doi.org/10.1002/cplu.201500390

Kurashov I.A., Kharlamova A.D., Abel A.S., Averin A.D., Beletskaya I.P. Molecules 2023, 28, 512. https://doi.org/10.3390/molecules28020512

Averin A.D., Ranyuk E.R., Lukashev N.V., Beletskaya I.P. Chemistry Eur. J. 2005, 11, 1730-1739. https://doi.org/10.1002/chem.200500784

Valkonen A., Sievänen E., Ikonen S., Lukashev N.V., Donez P.A., Averin A.D., Lahtinen M., Kolehmainen E. J. Mol. Struct. 2007, 846, 65-73. https://doi.org/10.1016/j.molstruc.2007.01.030

Averin A.D., Ranyuk E.R., Lukashev N.V., Golub S.L., Buryak A.K., Beletskaya I.P. Tetrahedron Lett. 2008, 49, 1188-1191. https://doi.org/10.1016/j.tetlet.2007.12.049

Averin A.D., Uglov A.N., Ranyuk E.R., Lukashev N.V., Beletskaya I.P. J. Org. Chem., 2009, 45, 273-284. https://doi.org/10.1134/S1070428009020213

Ranyuk E.R., Averin A.D., Beletskaya I.P. Adv. Synth. Catal. 2010, 352, 2299-2305. https://doi.org/10.1002/adsc.201000181

Grigorova O.K., Averin A.D., Maloshitskaya O.A., Rybakov V.B., Beletskaya I.P. Macroheterocycles 2016, 9, 418-424. https://doi.org/10.6060/mhc161069a

Grigorova O.K., Averin A.D., Maloshitskaya O.A., Beletskaya I.P. Macroheterocycles 2016, 9, 425-432. https://doi.org/10.6060/mhc161071a

Grigorova O.K., Averin A.D., Maloshitskaya O.A., Beletskaya I.P. Macroheterocycles 2017, 10, 446-453. https://doi.org/10.6060/mhc170937a

Averin A.D., Grigorova O.K., Malysheva A.S., Shaferov A.V., Beletskaya I.P. Pure Appl. Chem. 2020, 92, 1367-1386. https://doi.org/10.1515/pac-2020-0205

Beletskaya I.P. Averin A.D., Bessmertnykh A.G., Denat F., Guilard R. Tetrahedron Lett. 2002, 43, 1193-1196. https://doi.org/10.1016/S0040-4039(01)02356-5

Averin A.D., Shukhaev A.V., Buryak A.K., Denat F., Guilard R. Beletskaya I.P. Macroheterocycles 2009, 2, 281-285. https://doi.org/10.6060/mhc2009.3-4.281

Anokhin M.V., Averin A.D., Buryak A.K., Beletskaya I.P. Mendeleev Commun. 2011, 21, 132-133. https://doi.org/10.1016/j.mencom.2011.04.005

Anokhin M.V., Averin A.D., Buryak A.K., Beletskaya I.P. Russ. Chem. Bull. 2011, 60, 992-1003. https://doi.org/10.1007/s11172-011-0156-1

Chernichenko N.M., Averin A.D., Beletskaya I.P. Lett. Org. Chem., 2018, 15, 425-430. https://doi.org/10.2174/1570178615666171222151821

Yakushev A.A., Anokhin M.V., Averin A.D., Maloshitskaya O.A., Beletskaya I.P, Russ. Chem. Bull. 2012, 61, 1474-1482. https://doi.org/10.1007/s11172-012-0191-6

Kobelev S.M., Averin A.D., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2014, 7, 28-33. https://doi.org/10.6060/mhc140484a

Artamkina G.A., Sazonov P.K., Shtern M.M., Grishina G.V., Veselov I.S., Semeikin A.S., Syrbu S.A., Koifman O.I., Beletskaya I.P. Synlett 2008, 45-48. https://doi.org/10.1055/s-2007-992410

Artamkina G.A., Sazonov P.K., Shtern M.M., Grishina G.V., Veselov I.S., Semeikin A.S., Syrbu S.A., Koifman O.I., Beletskaya I.P. Russ. J. Org. Chem. 2008, 44, 421-431. https://doi.org/10.1134/S1070428008030184

Mikhalitsyna E.A., Tyurin V.S., Beletskaya I.P. J. Porphyrins Phthalocyanines 2015, 19, 874-886. https://doi.org/10.1142/S1088424615500637

Tyurin V.S., Mikhalitsyna E.A., Semeikin A.S., Beletskaya I.P. Macroheterocycles 2015, 8, 358-364. https://doi.org/10.6060/mhc150769b

Polevaya Y.P., Tyurin V.S., Beletskaya I.P. J. Porphyrins Phthalocyanines 2014, 18, 20-34. https://doi.org/10.1142/S1088424613500636

Yaschuk Y.P., Tyurin V.S., Beletskaya I.P. Macroheterocycles 2012, 5, 302-307. https://doi.org/10.6060/mhc2012.121199b

Mikhalitsyna E.A., Tyurin V.S., Khrustalev V.N., Lonin I.S., Beletskaya I.P. Dalton Trans. 2014, 43, 3563-3575. https://doi.org/10.1039/c3dt52685b

Mikhalitsyna E.A., Tyurin V.S., Zamilatskov I.A., Khrustalev V.N., Beletskaya I.P. Dalton Trans. 2012, 41, 7624-7637. https://doi.org/10.1039/c2dt30123g

Ranyuk E.R., Filatov M.A., Averin A.D., Cheprakov A.V., Beletskaya I.P. Synthesis 2012, 44, 393-398. https://doi.org/10.1055/s-0031-1289667

Yakushev A.A., Averin A.D., Maloshitskaya O.A., Syrbu S.A., Koifman O.I., Beletskaya I.P. Macroheterocycles 2016, 9, 65-72. https://doi.org/10.6060/mhc151206a

Yakushev A.A., Averin A.D., Maloshitskaya O.A., Syrbu S.A., Koifman O.I., Beletskaya I.P. Mendeleev Commun. 2016, 26, 199-201. https://doi.org/10.1016/j.mencom.2016.04.006

Averin A.D., Yakushev A.A., Maloshitskaya O.A., Syrbu S.A., Koifman O.I., Beletskaya I.P. Russ. Chem. Bull. 2017. 66, 1456-1466. https://doi.org/10.1007/s11172-017-1908-3

Yakushev A.A., Averin A.D., Maloshitskaya O.A., Koifman O.I., Syrbu S.A., Beletskaya I.P. Macroheterocycles 2018, 11, 135-140. https://doi.org/10.6060/mhc180276a

Yakushev A.A., Chernichenko N.M., Anokhin M.V., Averin A.D., Buryak A.K., Denat F., Beletskaya I.P. Molecules 2014, 19, 940-965. https://doi.org/10.3390/molecules19010940

Yakushev A.A., Averin A.D., Sakovich M.V., Vatsouro I.M., Kovalev V.V., Syrbu S.A., Koifman O.I., Beletskaya I.P. J. Porphyrins Phthalocyanines 2019, 23, 1551-1562. https://doi.org/10.1142/S1088424619501761

Koifman O.I., Ageeva T.A., Beletskaya I.P., Averin A.D., Yakushev A.A., Tomilova L.G., Dubinina T.V., Tsivadze A.Yu., Gorbunova Yu.G., Martynov A.G., Konarev D.V., Khasanov S.S., Lyubovskaya R.N., Lomova T.N., Korolev V.V., Zenkevich E.I., Blaudeck T., Ch. von Borczyskowski, Zahn D.R.T., Mironov A.F., Bragina N.A., Ezhov A.V., Zhdanova K.A., Stuzhin P.A., Pakhomov G.L., Rusakova N.V., Semenishyn N.N., Smola S.S., Parfenyuk V.I., Vashurin A.S., Makarov S.V., Dereven'kov I.A., Mamardashvili N.Zh., Kurtikyan T.S., Martirosyan G.G., Burmistrov V.А., Aleksandriiskii V.V., Novikov I.V., Pritmov D.A., Grin M.A., Suvorov N.V., Tsigankov A.A., Fedorov A.Yu., Kuzmina N.S., Nyuchev A.V., Otvagin V.F., Kustov A.V., Belykh D.V., Berezin D.B., Solovieva A.B., Timashev P.S., Milaeva E.R., Gracheva Yu.A., Dodokhova M.A., Safronenko A.V., Shpakovsky D.B., Syrbu S.A., Gubarev Yu.A., Kiselev A.N., Koifman M.O., Lebedeva N.Sh., Yurina E.S. Macroheterocycles 2020, 13, 311-467. https://doi.org/10.6060/mhc200814k

Abel A.S., Averin A.D., Buryak A.K., Orlinson B.S., Beletskaya I.P. Russ. Chem. Bull. 2014, 63, 102-108. https://doi.org/10.1007/s11172-014-0401-5

Averin A.D., Uglov A.N., Zubrienko G.A., Abel A.S., Buryak A.K., Beletskaya I.P. Russ. Chem. Bull. 2021, 70, 2164-2179. https://doi.org/10.1007/s11172-021-3328-7

Averin A.D., Uglov A.N., Zubrienko G.A., Tarasenko E.A., Buryak A.K., Beletskaya I.P. Curr. Org. Synth. 2017, 14, 918-926. https://doi.org/10.2174/1570179414666161230122852

Uglov A.N., Zubrienko G.A., Abel A.S., Averin A.D., Maloshitskaya O.A., Bessmertnykh-Lemeune A., Denat F., Beletskaya I.P. Heterocycles 2014, 88, 1213-1231. https://doi.org/10.3987/COM-13-S(S)87

Yakushev A.A., Anokhin M.V., Averin A.D., Maloshitskaya O.A., Savelyev E.N., Butov G.M., Orlinson B.S., Novakov I.A., Beletskaya I.P. Macroheterocycles 2013, 6, 40-46. https://doi.org/10.6060/mhc121214a

Chernichenko N.M., Averin A.D., Buryak A.K., Beletskaya I.P. Russ. Chem. Bull. 2014, 63, 2056-2063. https://doi.org/10.1007/s11172-014-0700-x

Averin A.D., Shukhaev A.V., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Tetrahedron Lett. 2008, 49, 3950-3954. https://doi.org/10.1016/j.tetlet.2008.04.045

Kobelev S.M., Averin A.D., Buryak A.K., Savelyev E.N., Orlinson B.S., Butov G.M., Novakov I.A., Denat F., Guilard R., Beletskaya I.P. ARKIVOC 2012, vii, 196-209. https://doi.org/10.3998/ark.5550190.0013.713

Averin A.D., Tyutenov K.S., Shukhaev A.V., Kobelev S.M., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Heterocycles 2012, 86, 1341-1366. https://doi.org/10.3987/COM-12-S(N)88

Averin A.D., Shukhaev A.V., Vovk A.I., Kukhar V.P., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2014, 7, 174-180. https://doi.org/10.6060/mhc140502a

Kobelev S.M., Averin A.D., Buryak A.K., Vovk A.I., Kukhar V.P., Denat F., Guilard R., Beletskaya I.P. Heterocycles 2015, 90, 989-1017. https://doi.org/10.3987/COM-14-S(K)71

Kobelev S.M., Averin A.D., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Heterocycles 2011, 82, 1447-1476. https://doi.org/10.3987/COM-10-S(E)98

Kobelev S.M., Averin A.D., Maloshitskaya O.A., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2012, 5, 389-395. https://doi.org/10.6060/mhc2012.121102a

Chernichenko N.M., Shevchuk V.N., Averin A.D., Maloshitskaya O.A., Beletskaya I.P. Synlett 2017, 28, 2800-2806. https://doi.org/10.1055/s-0036-1590883

Averin A.D., Chernichenko N.M., Shevchuk V.N., Maloshitskaya O.A., Denat F., Beletskaya I.P. Macroheterocycles 2018, 11, 141-149. https://doi.org/10.6060/mhc171255a

Kobelev S.M., Averin A.D., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Tetrahedron Lett. 2012, 53, 210-213. https://doi.org/10.1016/j.tetlet.2011.11.024

Kobelev S.M., Averin A.D., Buryak A.K., Denat F., Guilard R., Beletskaya I.P. Macroheterocycles 2014, 7, 28-33. https://doi.org/10.6060/mhc140484a

Grigorova O.K., Gusev D.I., Averin A.D., Maloshitskaya O.A., Beletskaya I.P. Russ. Chem. Bull. 2019, 68, 848-854. https://doi.org/10.1007/s11172-019-2495-2

Grigorova O.K., Averin A.D., Maloshitskaya O.A., Denat F., Beletskaya I.P. Macroheterocycles 2019, 12, 312-318. https://doi.org/10.6060/mhc190337a

Опубликован
2023-08-11
Как цитировать
Averin, A., Abel, A., Malysheva, A., Chernichenko, N., & Yakushev, A. (2023). Palladium-Catalyzed Amination for the Synthesis of Macrocycles and Polymacrocycles: Contribution of Professor I.P. Beletskaya. Макрогетероциклы/Macroheterocycles, 16(2), 92-108. https://doi.org/10.6060/mhc235004a