Skip to main content
SpringerLink
Log in

Symposium on the Chemistry of Alkynes, Allenes, and Small Rings

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The symposium on the chemistry of alkynes, allenes, and small rings was held on July 3–6, 2023 at St. Petersburg State University as part of the All-Russian conference with international participation “Ideas and Legacy of A.E. Favorsky in Organic Chemistry.” Leading experts in the chemistry of alkynes, allenes, and small rings took part in the conference, recent advances in the chemistry of compounds of these classes were presented, and prospects for further development of this research field were discussed. Brief annotations of the reports made and references to the relevant publications of the authors are collected in the present review.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

REFERENCES

  1. Favorskaya, T.A., Aleksei Evgrafovich Favorskii (1860–1945), Leningrad: Nauka, 1980.

  2. Konovalov, A.I., Antipin, I.S., Burilov, V.A., Madzhi­dov, T.I., Kurbangalieva, A.R., Nemtarev, A.V., Solovie­va, S.E., Stoikov, I.I., Mamedov, V.A., Zakharova, L.Ya., Gavrilova, E.L., Sinyashin, O.G., Balova, I.A., Va­silyev, A.V., Zenkevich, I.G., Krasa­vin, M.Yu., Kuznetsov, M.A., Molchanov, A.P., Novikov, M.S., Nikolaev, V.A., Rodina, L.L., Khlebnikov, A.F., Beletskaya, I.P., Vatsadze, S.Z., Gromov, S.P., Zyk, N.V., Lebedev, A.T., Lemenov­skii, D.A., Petrosyan, V.S., Nenaidenko, V.G., Negrebetskii, V.V., Baukov, Yu.I., Shmigol’, T.A., Kor­lyu­kov, A.A., Tikhomirov, A.S., Shchekotikhin, A.E., Traven’, V.F., Voskresenskii, L.G., Zubkov, F.I., Golubchikov, O.A., Semeikin, A.S., Berezin, D.B., Stuzhin, P.A., Filimo­nov, V.D., Krasnokutskaya, E.A., Fedorov, A.Yu., Nyuchev, A.V., Orlov, V.Yu., Begu­nov, R.S., Rusa­kov, A.I., Kolobov, A.V., Kofanov, E.R., Fedotova, O.V., Egorova, A.Yu., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Osyanin, V.A., Reznikov, A.N., Fisyuk, A.S., Sagitullina, G.P., Akse­nov, A.V., Akse­nov, N.A., Grachev, M.K., Maslenniko­va, V.I., Koro­teev, M.P., Brel’, A.K., Lisina, S.V., Medvedeva, S.M., Shikhaliev, Kh.S., Suboch, G.A., Tovbis, M.S., Mironovich, L.M., Ivanov, S.M., Kurba­tov, S.V., Kletskii, M.E., Burov, O.N., Kobrakov, K.I., and Kuzne­tsov, D.N., Russ. J. Org. Chem. 2018, vol. 54, p. 157. https://doi.org/10.1134/S107042801802001X

  3. Favorskii, A.E. and Skosarevskii, M.L., Zh. Russ. Fiz.-Khim. O-va., 1900, vol. 32, p. 652.

    Google Scholar 

  4. Favorskii, A.E., Zh. Russ. Fiz.-Khim. O-va., 1886, vol. 18, p. 319.

    Google Scholar 

  5. Menshutkin, B.N., Favorskii, A.E., and Myakotin, A., Zh. Russ. Fiz.-Khim. O-va., 1901, vol. 33, p. 631.

    Google Scholar 

  6. Danilkina, N.A., Vasileva, A.A., and Balova, I.A., Russ. Chem. Rev., 2020, vol. 89, p. 125. https://doi.org/10.1070/RCR4902

    Article  CAS  ADS  Google Scholar 

  7. Abstracts of Papers, Vserossiiskaya konferentsiya s mezh­dunarodnym uchastiem “Idei i nasledie A.E. Favorskogo v organicheskoi khimii” (All-Russian Conf. with Int. Participation “Ideas and Legacy of A.E. Favorsky in Or­ganic Chemistry”), St. Petersburg: VVM, July 3–6, 2023.

  8. Beletskaya, I.P. and Kustov, L.M., Russ. Chem. Rev., 2010, vol. 79, p. 441. https://doi.org/10.1070/RC2010v079n06ABEH004137

    Article  CAS  ADS  Google Scholar 

  9. Tarasenko, E.A., Shestakov, I.V., Rybakov, V.B., and Beletskaya, I.P., ChemCatChem, 2019, vol. 11, p. 3913. https://doi.org/10.1002/cctc.201900575

    Article  CAS  Google Scholar 

  10. Mitrofanov, A.Yu., Bychkova, V.A., Nefedov, S.E., and Beletskaya, I.P., J. Org. Chem., 2020, vol. 85, p. 14507. https://doi.org/10.1021/acs.joc.0c00913

    Article  CAS  PubMed  Google Scholar 

  11. Mitrofanov, A.Yu. and Beletskaya, I.P., J. Org. Chem., 2023, vol. 88, p. 2367. https://doi.org/10.1021/acs.joc.2c02780

    Article  CAS  PubMed  Google Scholar 

  12. Morozkov, G.V., Abel, A.S., Filatov, M.A., Nefe­dov, S.E., Roznyatovsky, V.A., Cheprakov, A.V., Mitro­fanov, A.Yu., Ziankou, I.S., Averin, A.D., Belets­kaya, I.P., Michalak, J., Bucher, C., Bonneviot, L., and Bessmertnykh-Lemeune, A., Dalton Trans., 2022, vol. 51, p. 13612. https://doi.org/10.1039/D2DT01364A

    Article  CAS  PubMed  Google Scholar 

  13. Alabugin, I.V. and Gonzalez-Rodriguez, E., Acc. Chem. Res., 2018, vol. 51, p. 1206. https://doi.org/10.1021/acs.accounts.8b00026

    Article  CAS  PubMed  Google Scholar 

  14. Alabugin, I.V., Kuhn, L., Medvedev, M.G., Krivoshchapov, N.V., Vil’, V.A., Yaremenko, I.A., Mehaffy, P., Yarie, M., Terent’ev, A.O., and Zolfigol, M.A., Chem. Soc. Rev., 2021, vol. 50, p. 10253. https://doi.org/10.1039/D1CS00386K

    Article  CAS  PubMed  Google Scholar 

  15. Yaremenko, I.A., Belyakova, Y.Y., Radulov, P.S., Novikov, R.A., Medvedev, M.G., Krivoshchapov, N.V., Korlyukov, A.A., Alabugin, I.V., and Terent’ev, A.O., J. Am. Chem. Soc., 2021, vol. 143, p. 6634. https://doi.org/10.1021/jacs.1c02249

    Article  CAS  PubMed  Google Scholar 

  16. Elliott, Q., Gomes, G., Evoniuk, C.J., and Alabugin, I.V., Chem. Sci., 2020, vol. 11, p. 6539. https://doi.org/10.1039/C9SC06511C

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Syroeshkin, M.A., Kuriakose, F., Saverina, E.A., Timofeeva, V.A., Egorov, M.P., and Alabugin, I.V., Angew. Chem., Int. Ed., 2019, vol. 58, p. 5532. https://doi.org/10.1002/anie.201807247

    Article  CAS  Google Scholar 

  18. Galushko, A.S., Boiko, D.A., Pentsak, E.O., Eremin, D.B., and Ananikov, V.P., J. Am. Chem. Soc., 2023, vol. 145, p. 9092. https://doi.org/10.1021/jacs.3c00645

    Article  CAS  PubMed  Google Scholar 

  19. Eremin, D.B., Galushko, A.S., Boiko, D.A., Pentsak, E.O., Chistyakov, I.V., and Ananikov, V.P., J. Am. Chem. Soc., 2022, vol. 144, p. 6071. https://doi.org/10.1021/jacs.2c01283

    Article  CAS  PubMed  Google Scholar 

  20. Boiko, D.A., Kozlov, K.S., Burykina, Yu.V., Ilyushen­kova, V.V., and Ananikov, V.P., J. Am. Chem. Soc., 2022, vol. 144, p. 14590. https://doi.org/10.1021/jacs.2c03631

    Article  CAS  PubMed  Google Scholar 

  21. Boiko, D.A., Pentsak, E.O., Cherepanova, V.A., Gordeev, E.G., and Ananikov, V.P., Chem. Sci., 2021, vol. 12, p. 7428. https://doi.org/10.1039/D0SC05696K

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Kashin, A.S., Boiko, D.A., and Ananikov, V.P., Small, 2021, vol. 17, article ID 2007726. https://doi.org/10.1002/smll.202007726

  23. Schmidt, E.Yu., Bidusenko, I.A., Protsuk, N.I., Demyanov, Y.V., Ushakov, I.A., and Trofimov, B.A., Eur. J. Org. Chem., 2019, vol. 2019, p. 5875. https://doi.org/10.1002/ejoc.201900932

    Article  CAS  Google Scholar 

  24. Bidusenko, I.A., Schmidt, E.Yu., Ushakov, I.A., Vashchenko, A.V., and Trofimov, B.A., Org. Lett., 2021, vol. 23, p. 4121. https://doi.org/10.1021/acs.orglett.1c01009

    Article  CAS  PubMed  Google Scholar 

  25. Bidusenko, I.A., Schmidt, E.Yu., Ushakov, I.A., Vashchenko, A.V., Protsuk, N.I., Orel, V.B., and Vitkovskaya, N.M., and Trofimov, B.A., J. Org. Chem., 2022, vol. 87, p. 12225. https://doi.org/10.1021/acs.joc.2c01372

    Article  CAS  PubMed  Google Scholar 

  26. Semenova, N.V., Schmidt, E.Yu., Ushakov, I.A., Vashchenko, A.V., and Trofimov, B.A., Mendeleev Commun., 2023, vol. 33, p. 164. https://doi.org/10.1016/j.mencom.2023.02.005

    Article  CAS  Google Scholar 

  27. Volkov, P.A., Khrapova, K.O., Telezhkin, A.A., Bidusenko, I.A., Schmidt, E.Yu., Albanov, A.I., and Trofimov, B.A., Adv. Synth. Catal., 2023, vol. 365, p. 53. https://doi.org/10.1002/adsc.202201179

    Article  CAS  Google Scholar 

  28. Zerov, A.V., Boyarskaya, I.A., Khoroshilova, O.V., Lavrentieva, I.N., Slita, A.V., Sinegubova, E.O., Zarubaev, V.V., and Vasilyev, A.V., J. Org. Chem., 2021, vol. 86, p. 1489. https://doi.org/10.1021/acs.joc.0c02361

    Article  CAS  PubMed  Google Scholar 

  29. Devleshova, N.A., Lozovskiy, S.V., and Vasilyev, A.V., Tetrahedron, 2019, vol. 75, article ID 130517. https://doi.org/10.1016/j.tet.2019.130517

  30. Nursahedova, S.K., Ryabukhin, D.S., Muzalev­skiy, V.M., Iakovenko, R.O., Boyarskaya, I.A., Starova, G.L., Nenajdenko, V.G., and Vasilyev, A.V., Eur. J. Org. Chem., 2019, vol. 2019, p. 1293. https://doi.org/10.1002/ejoc.201801645

    Article  CAS  Google Scholar 

  31. Nursahedova, S.K., Zerov, A.V., Boyarskaya, I.A., Grinenko, E.V., Nenajdenko, V.G., and Vasilyev, A.V., Org. Biomol. Chem., 2019, vol. 17, p. 1215. https://doi.org/10.1039/C8OB02887G

    Article  CAS  PubMed  Google Scholar 

  32. Zerov, A.V., Kazakova, A.N., Boyarskaya, I.A., Panikorovskii, T.L., Suslonov, V.V., Khoroshilova, O.V., and Vasilyev, A.V., Molecules, 2018, vol. 23, article no. 3079. https://doi.org/10.3390/molecules23123079

  33. Lyapunova, A.G., Danilkina, N.A., Rumyantsev, A.M., Khlebnikov, A.F., Chislov, M.V., Starova, G.L., Sambuk, E.V., Govdi, A.I., Bräse, S., and Balova, I.A., J. Org. Chem., 2018, vol. 83, p. 2788. https://doi.org/10.1021/acs.joc.7b03258

    Article  CAS  PubMed  Google Scholar 

  34. Danilkina, N.A., D’yachenko, A.S., Govdi, A.I., Khlebnikov, A.F., Kornyakov, I.V., Bräse, S., and Balova, I.A., J. Org. Chem., 2020, vol. 85, p. 9001. https://doi.org/10.1021/acs.joc.0c00930

    Article  CAS  PubMed  Google Scholar 

  35. Danilkina, N.A., Govdi, A.I., Khlebnikov, A.F., Tikhomirov, A.O., Sharoyko, V.V., Shtyrov, A.A., Ryazantsev, M.N., Bräse, S., and Balova, I.A., J. Am. Chem. Soc., 2021, vol. 143, p. 16519. https://doi.org/10.1021/jacs.1c06041

    Article  CAS  PubMed  Google Scholar 

  36. Motornov, V.A., Muzalevskiy, V.M., Tabolin, A.A., Novikov, R.A., Nelyubina, Y.V., Nenajdenko, V.G., and Ioffe, S.L., J. Org. Chem., 2017, vol. 82, p. 5274. https://doi.org/10.1021/acs.joc.7b00578

    Article  CAS  PubMed  Google Scholar 

  37. Larkovich, R.V., Shambalova, V.E., Ponomarev, S.A., Aldoshin, A.S., Lyssenko, K.A., Nechaev, M.S., and Nenajdenko, V.G., J. Org. Chem., 2023, vol. 88, p. 10122. https://doi.org/10.1021/acs.joc.3c00935

    Article  CAS  PubMed  Google Scholar 

  38. Ponomarev, S.A., Larkovich, R.V., Aldoshin, A.S., Tabolin, A.A., Ioffe, S.L., Groß, J., Opatz, T., and Nenajdenko, V.G., Beilstein J. Org. Chem., 2021, vol. 17, p. 283. https://doi.org/10.3762/bjoc.17.27

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Galenko, E.E., Kryukova, M.A., Novikov, M.S., and Khlebnikov, A.F., J. Org. Chem., 2020, vol. 85, p. 6109. https://doi.org/10.1021/acs.joc.0c00611

    Article  CAS  PubMed  Google Scholar 

  40. Agafonova, A.V., Funt, L.D., Novikov, M.S., and Khlebnikov, A.F., Org. Biomol. Chem., 2021, vol. 19, p. 1976. https://doi.org/10.1039/d1ob00053e

    Article  CAS  PubMed  Google Scholar 

  41. Agafonova, A.V., Novikov, M.S., and Khlebnikov, A.F., Molecules, 2023, vol. 28, article no. 275. https://doi.org/10.3390/molecules28010275

  42. Oparina, L.A., Belyaeva, K.V., Koluvanov, N.A., Ushakov, I.A., Gotsko, M.D., Sobenina, L.N., Vashchenko, A.V., and Trofimov, B.A., J. Org. Chem., 2022, vol. 87, p. 9518. https://doi.org/10.1021/acs.joc.2c00476

    Article  CAS  PubMed  Google Scholar 

  43. Belyaeva, K.V., Nikitina, L.P., Gen’, V.S., Tomilin, I.V., Sobenina, L.N., Afonin, A.V., Oparina, L.A., and Trofimov, B.A., Catalysts, 2022, vol. 12, article no. 1604. https://doi.org/10.3390/catal12121604

  44. Belyaeva, K.V., Nikitina, L.P., Gen’, V.S., Saliy, I.V., Sobenina, L.N., Afonin, A.V., Vashchenko, A.V., and Trofimov, B.A., ChemistrySelect, 2022, vol. 7, article ID e20220448. https://doi.org/10.1002/slct.202204482

  45. Gulevskaya, A.V. and Nelina-Nemtseva, J.I., Chem. Heterocycl. Compd., 2018, vol. 54, p. 1084. https://doi.org/10.1007/s10593-019-02398-5

    Article  CAS  Google Scholar 

  46. Gulevskaya, A.V. and Tonkoglazova, D.I., Adv. Synth. Catal., 2022, vol. 364, p. 2502. https://doi.org/10.1002/adsc.202200513

    Article  CAS  Google Scholar 

  47. De, A., Santra, S., Hajra, A., Zyryanov, G.V., and Majee, A., J. Org. Chem., 2019, vol. 84, p. 11735. https://doi.org/10.1021/acs.joc.9b01625

    Article  CAS  PubMed  Google Scholar 

  48. Rahman, M., Bagdi, A.K., Kopchuk, D.S., Kovalev, I.S., Zyryanov, G.V., Chupakhin, O.N., Majee, A., and Hajra, A., Org. Biomol. Chem., 2020, vol. 18, p. 9562. https://doi.org/10.1039/D0OB01638A

    Article  CAS  PubMed  Google Scholar 

  49. Mahato, S., Santra, S., Zyryanov, G.V., and Majee, A., J. Org. Chem., 2019, vol. 84, p. 3176. https://doi.org/10.1021/acs.joc.8b03065

    Article  CAS  PubMed  Google Scholar 

  50. Khlebnikov, A.F., Novikov, M.S., and Rostovskii, N.V., Tetrahedron, 2019, vol. 75, p. 2555. https://doi.org/10.1016/j.tet.2019.03.040

    Article  CAS  Google Scholar 

  51. Sakharov, P.A., Novikov, M.S., and Rostovskii, N.V., Chem. Heterocycl. Compd., 2021, vol. 57, p. 512. https://doi.org/10.1007/s10593-021-02934-2

    Article  CAS  Google Scholar 

  52. Sakharov, P.A., Rostovskii, N.V., Khlebnikov, A.F., Khoroshilova, O.V., and Novikov, M.S., Adv. Synth. Catal., 2019, vol. 361, p. 3359. https://doi.org/10.1002/adsc.201900366

    Article  CAS  Google Scholar 

  53. Sakharov, P.A., Rostovskii, N.V., Khlebnikov, A.F., Panikorovskii, T.L., and Novikov, M.S., Org. Lett., 2019, vol. 21, p. 3615. https://doi.org/10.1021/acs.orglett.9b01043

    Article  CAS  PubMed  Google Scholar 

  54. Sakharov, P.A., Rostovskii, N.V., Khlebnikov, A.F., and Novikov, M.S., Molecules, 2022, vol. 27, article no. 5681. https://doi.org/10.3390/molecules27175681

  55. Ankudinov, N.M., Chusov, D.A., Nelyubina, Y.V., and Perekalin, D.S., Angew. Chem., Int. Ed., 2021, vol. 60, p. 18712. https://doi.org/10.1002/anie.202105179

    Article  CAS  Google Scholar 

  56. Trifonova, E.A., Ankudinov, N.M., Chusov, D.A., Nelyubina, Y.V., and Perekalin, D.S., Chem. Commun., 2022, vol. 58, p. 6709. https://doi.org/10.1039/D2CC01648F

    Article  CAS  Google Scholar 

  57. Ivanova, O.A. and Trushkov, I.V., Chem. Rec., 2019, vol. 19, p. 2189. https://doi.org/10.1002/tcr.201800166

    Article  CAS  PubMed  Google Scholar 

  58. Chagarovskiy, A.O., Vasin, V.S., Kuznetsov, V.V., Ivanova, O.A., Rybakov, V.B., Shumsky, A.N., Makho­va, N.N., and Trushkov, I.V., Angew. Chem., Int. Ed., 2018, vol. 57, p. 10338. https://doi.org/10.1002/anie.201805258

    Article  CAS  Google Scholar 

  59. Agafonova, A.V., Smetanin, I.A., Rostovskii, N.V., Khlebnikov, A.F., and Novikov, M.S., Org. Lett., 2021, vol. 23, p. 8045. https://doi.org/10.1021/acs.orglett.1c03060

    Article  CAS  PubMed  Google Scholar 

  60. Agafonova, A.V., Golubev, A.A., Smetanin, I.A., Khleb­nikov, A.F., Spyridonova, D.V., and Novikov, M.S., Org. Lett., 2023, vol. 25, p. 7165. https://doi.org/10.1021/acs.orglett.3c02696

    Article  CAS  PubMed  Google Scholar 

  61. Kotovshchikov, Y.N., Tatevosyan, S.S., Latyshev, G.V., Kugusheva, Z.R., Lukashev, N.V., and Beletskaya, I.P., New J. Chem., 2023, vol. 47, p. 12239. https://doi.org/10.1039/D3NJ01264F

    Article  CAS  Google Scholar 

  62. Bobrova, A.Yu., Novikov, M.A., and Tomilov, Yu.V., Org. Biomol. Chem., 2021, vol. 21, p. 4678. https://doi.org/10.1039/D1OB00567G

    Article  Google Scholar 

  63. Bobrova, A.Yu., Novikov, M.A., and Tomilov, Yu.V., Mendeleev Commun., 2022, vol. 32, no. 5, p. 619. https://doi.org/10.1016/j.mencom.2022.09.016

    Article  CAS  Google Scholar 

  64. Boichenko, M.A., Ivanova, O.A., Andreev, I.A., Chagarovskiy, A.O., Levina, I.I., Rybakov, V.B., Skvortsov, D.A., and Trushkov, I.V., Org. Chem. Front., 2018, vol. 5, p. 2829. https://doi.org/10.1039/C8QO00742J

    Article  CAS  Google Scholar 

  65. Boichenko, M.A., Andreev, I.A., Chagarovskiy, A.O., Levina, I.I., Zhokhov, S.S., Trushkov, I.V., and Ivanova, O.A., J. Org. Chem., 2020, vol. 85, p. 1146. https://doi.org/10.1021/acs.joc.9b03098

    Article  CAS  PubMed  Google Scholar 

  66. Andreev, I.A., Boichenko, M.A., Ratmanova, N.K., Ivanova, O.A., Levina, I.I., Khrustalev, V.N., Sedov, I.A., and Trushkov, I.V., Adv. Synth. Catal., 2022, vol. 364, p. 2403. https://doi.org/10.1002/adsc.202200486

    Article  CAS  Google Scholar 

  67. Boichenko, M.A., Plodukhin, A.Y., Shorokhov, V.V., Lebedev, D.S., Filippova, A.V., Zhokhov, S.S., Tarasenko, E.A., Rybakov, V.B., Trushkov, I.V., and Ivanova, O.A., Molecules, 2022, vol. 27, article no. 8468. https://doi.org/10.3390/molecules27238468

  68. Shorokhov, V.V., Lebedev, D.S., Boichenko, M.A., Zhokhov, S.S., Trushkov, I.V., and Ivanova, O.A., Chem. Heterocycl. Compd., 2023, vol. 59, p. 54. https://doi.org/10.1007/s10593-023-03162-6

    Article  CAS  Google Scholar 

  69. Vatsadze, S.Z., Medved’ko, A.V., Bodunov, A.A., and Lyssenko, K.A., Mendeleev Commun., 2020, vol. 30, p. 344. https://doi.org/10.1016/j.mencom.2020.05.028

    Article  CAS  Google Scholar 

  70. Vidyakina, A.A., Shtyrov, A.A., Ryazantsev, M.N., Khlebnikov, A.F., Kolesnikov, I.E., Sharoyko, V.V., Spyridonova, D.V., Balova, I.A., Bräse, S., and Danilkina, N.A., Chem. Eur. J., 2023, vol. 29, article ID e202300540. https://doi.org/10.1002/chem.202300540

  71. Vil’, V.A., Barsegyan, Y.A., Kuhn, L., Terent’ev, A.O., and Alabugin, I.V., Organometallics, 2023, vol. 42, p. 2598. https://doi.org/10.1021/acs.organomet.2c00663

    Article  CAS  Google Scholar 

  72. Vorobyeva, D.V., Bubnova, A.S., Godovikov, I.A., Danshina, A.A., and Osipov, S.N., Asian J. Org. Chem., 2022, vol. 12, article ID e202200485. https://doi.org/10.1002/ajoc.202200485

  73. Vorobyeva, D.V., Petropavlovskikh, D.A., Godovi­kov, I.A., Dolgushin, F.M., and Osipov, S.N., Molecules, 2022, vol. 27, article no. 8488. https://doi.org/10.3390/molecules27238488

  74. Tokareva, M.A., Pernik, I., Lewis, W., Messerle, B.A., Glukhareva, T.V., and Keaveney, S.T., ACS Catal., 2022, vol. 12, p. 5574. https://doi.org/10.1021/acscatal.2c01175

    Article  CAS  Google Scholar 

  75. Tokareva, M.A., Pernik, I., Messerle, B.A., Glukhare­va, T.V., and Keaveney, S.T., Catal. Sci. Technol., 2023, vol. 13, p. 2772. https://doi.org/10.1039/D3CY00290J

    Article  CAS  Google Scholar 

  76. Govdi, A.I., Danilkina, N.A., Ponomarev, A.V., and Balova, I.A., J. Org. Chem., 2019, vol. 84, p. 1925. https://doi.org/10.1021/acs.joc.8b02916

    Article  CAS  PubMed  Google Scholar 

  77. Efremova, M.M., Govdi, A.I., Frolova, V.V., Rumyan­tsev, A.M., and Balova, I.A., Molecules, 2021, vol. 26, article no. 2801. https://doi.org/10.3390/molecules26092801

  78. Govdi, A.I., Tokareva, P.V., Rumyantsev, A.M., Pa­nov, M.S., Stellmacher, J., Alexiev, U., Danilkina, N.A., and Balova, I.A., Molecules, 2022, vol. 27, article no. 3191. https://doi.org/10.3390/molecules27103191

  79. Spivak, A.Y., Gubaidullin, R.R., Galimshina, Z.R., Nedopekina, D.A., and Odinokov, V.N., Tetrahedron, 2016, vol. 72, p. 1249. https://doi.org/10.1016/j.tet.2016.01.024

    Article  CAS  Google Scholar 

  80. Gubaidullin, R.R., Spivak, A.Yu., Maistrenko, V.N., and Parfenova, L.V., ChemistrySelect, 2022, vol. 7, article ID e202202241. https://doi.org/10.1002/slct.202202241

  81. Itakhunov, R.N., Odin, I.S., Gusev, D.M., Grabov­skiy, S.A., Gordon, K.V., Vologzhanina, A.V., Sokov, S.A., Sosnin, I.M., and Golovanov, A.A., Org. Biomol. Chem., 2022, vol. 20, p. 8693. https://doi.org/10.1039/D2OB01427K

    Article  CAS  PubMed  Google Scholar 

  82. Shcherbakov, N.V., Titov, G.D., Chikunova, E.I., Filippov, I.P., Rostovskii, N.V., Kukushkin, V.Yu., and Dubovtsev, A.Yu., Org. Chem. Front., 2022, vol. 9, p. 5133. https://doi.org/10.1039/D2QO01105K

    Article  CAS  Google Scholar 

  83. Efremova, M.M., Makarova, A.A., Novikov, A.S., Kryu­kova, M.A., Kuznetsov, M.A., and Molchanov, A.P., Org. Biomol. Chem., 2021, vol. 19, p. 9773. https://doi.org/10.1039/D1OB01584B

    Article  CAS  PubMed  Google Scholar 

  84. Zakharov, T.N., Sakharov, P.A., Novikov, M.S., Khleb­nikov, A.F., and Rostovskii, N.V., Molecules, 2023, vol. 28, article no. 4315. https://doi.org/10.3390/molecules28114315

  85. Ivanova, E.E., Shabalin, D.A., Ushakov, I.A., Vashchenko, A.V., Schmidt, E.Yu., and Trofimov, B.A., Org. Biomol. Chem., 2023, vol. 21, p. 1725. https://doi.org/10.1039/D2OB02230C

    Article  CAS  PubMed  Google Scholar 

  86. Vartanova, A.E., Plodukhin, A.Yu., Ratmanova, N.K., Andreev, I.A., Anisimov, M.N., Gudimchuk, N.B., Ry­ba­kov, V.B., Levina, I.I., Ivanova, O.A., Trushkov, I.V., and Alabugin, I.V., J. Am. Chem. Soc., 2021, vol. 143, p. 13952. https://doi.org/10.1021/jacs.1c07088

    Article  CAS  PubMed  Google Scholar 

  87. Fadeev, A.A., Makarov, A.S., Ivanova, O.A., Uchus­kin, M.G., and Trushkov, I.V., Org. Chem. Front., 2022, vol. 9, p. 737. https://doi.org/10.1039/D1QO01646F

    Article  CAS  Google Scholar 

  88. Kolos, A.V., Nelyubina, Y.V., Sundararaju, B., and Perekalin, D.S., Organometallics, 2021, vol. 40, p. 3712. https://doi.org/10.1021/acs.organomet.1c00403

    Article  CAS  Google Scholar 

  89. Trifonova, E.A., Ankudinov, N.M., Mikhaylov, A.A., Chusov, D.A., Nelyubina, Y.V., and Perekalin, D.S., Angew. Chem., Int. Ed., 2018, vol. 57, p. 7714. https://doi.org/10.1002/anie.201801703

    Article  CAS  Google Scholar 

  90. Komarova, A.A. and Perekalin, D.S., Organometallics, 2023, vol. 42, p. 1433. https://doi.org/10.1021/acs.organomet.3c00153

    Article  CAS  Google Scholar 

  91. Dar’in, D., Kantin, G., Chupakhin, E., Sharoyko, V., and Krasavin, M., Chem. Eur. J., 2021, vol. 27, p. 8221, https://doi.org/10.1002/chem.202100880

    Article  CAS  PubMed  Google Scholar 

  92. Dar’in, D., Kantin, G., Glushakova, D., Sharoyko, V., and Krasavin, M., J. Org. Chem., in press. https://doi.org/10.1021/acs.joc.2c02600

  93. Shcherbakov, R.O., Myasnikov, D.A., Trushkov, I.V., and Uchuskin, M.G., J. Org. Chem., 2023, vol. 88, p. 8227. https://doi.org/10.1021/acs.joc.3c00203

    Article  CAS  PubMed  Google Scholar 

  94. Pelipko, V.V., Baichurin, R.I., Lyssenko, K.A., Kondrashov, E.V., and Makarenko, S.V., Mendeleev Commun., 2023, vol. 33, p. 451. https://doi.org/10.1016/j.mencom.2023.06.003

    Article  CAS  Google Scholar 

  95. Sakharov, P.A., Koronatov, A.N., Khlebnikov, A.F., Novikov, M.S., Glukharev, A.G., Rogacheva, E.V., Kraeva, L.A., Sharoyko, V.V., Tennikova, T.B., and Rostovskii, N.V., RSC Adv., 2019, vol. 9, p. 37901. https://doi.org/10.1039/C9RA09345A

    Article  CAS  PubMed  PubMed Central  ADS  Google Scholar 

  96. Rostovskii, N.V., Koronatov, A.N., Sakharov, P.A., Agafonova, A.V., Novikov, M.S., Khlebnikov, A.F., Rogacheva, E.V., and Kraeva, L.A., Org. Biomol. Chem., 2020, vol. 18, p. 9448. https://doi.org/10.1039/D0OB02023K

    Article  CAS  PubMed  Google Scholar 

  97. Titov, G.D., Antonychev, G.I., Novikov, M.S., Khlebnikov, A.F., Rogacheva, E.V., Kraeva, L.A., and Rostovskii, N.V., Org. Lett., 2023, vol. 25, p. 2707. https://doi.org/10.1021/acs.orglett.3c00823

    Article  CAS  PubMed  Google Scholar 

  98. Dvorko, M.Yu., Shabalin, D.A., Ushakov, I.A., Schmidt, E.Yu., and Trofimov, B.A., Eur. J. Org. Chem., 2023, vol. 26, article ID e202201464. https://doi.org/10.1002/ejoc.202201464

  99. Samultceva, S.O., Dvorko, M.Yu., Shabalin, D.A., Ushakov, I.A., Vashchenko, A.V., Schmidt, E.Yu., and Trofimov, B.A., Org. Biomol. Chem., 2022, vol. 20, p. 5325. https://doi.org/10.1039/D2OB00854H

    Article  CAS  PubMed  Google Scholar 

  100. Sergeev, P.G., Novikov, R.A., and Tomilov, Y.V., Adv. Synth. Catal., 2021, vol. 363, p. 5292. https://doi.org/10.1002/adsc.202101198

    Article  CAS  Google Scholar 

  101. Sergeev, P.G., Novikov, R.A., and Tomilov, Y.V., Molecules, 2023, vol. 28, p. 88. https://doi.org/10.3390/molecules28010088

    Article  CAS  Google Scholar 

  102. Soldatova, N.S., Semenov, A.V., Geyl, K.K., Baykov, S.V., Shetnev, A.A., Konstantinova, A.S., Korsakov, M.M., Yusubov, M.S., and Postnikov, P.S., Adv. Synth. Catal., 2021, vol. 363, p. 3566. https://doi.org/10.1002/adsc.202100426

    Article  CAS  Google Scholar 

  103. Podrezova, E.V., Okhina, A.A., Rogachev, A.D., Baykov, S.V., Kirschning, A., Yusubov, M.S., Soldatova, N.S., and Postnikov, P.S., Org. Biomol. Chem., 2023, vol. 21, p. 1952. https://doi.org/10.1039/D2OB02122F

    Article  CAS  PubMed  Google Scholar 

  104. Obydennov, D.L., Goncharov, A.O., and Sosnov­skikh, V.Ya., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, p. 2233. https://doi.org/10.1007/s11172-016-1574-x

    Article  CAS  Google Scholar 

  105. Obydennov, D.L., Viktorova, V.V., Chernyshova, E.V., Shirinkin, A.S., Usachev, S.A., and Sosnovskikh, V.Y., Synthesis, 2020, vol. 52, p. 2267. https://doi.org/10.1055/s-0040-1707471

    Article  CAS  Google Scholar 

  106. Steparuk, E.V., Meshcheryakova, E.A., Viktoro­va, V.V., Ulitko, M.V., Obydennov, D.L., and Sosnov­skikh, V.Y., J. Org. Chem., 2023, vol. 88, p. 11590. https://doi.org/10.1021/acs.joc.3c00907

    Article  CAS  PubMed  Google Scholar 

  107. Steparuk, E.V., Obydennov, D.L., and Sosnov­skikh, V.Y., Molbank, 2023, vol. 2023, article no. M1668. https://doi.org/10.3390/M1668

  108. Munkuev, A.A., Dyrkheeva, N.S., Kornienko, T.E., Ilina, E.S., Ivankin, D.I., Suslov, E.V., Korchagi­na, D.V., Gatilov, Y.V., Zakharenko, A.L., Malakho­va, A.A., Reynisson, J., Volcho, K.P., Salakhutdi­nov, N.F., and Lavrik, O.I., Molecules, 2022, vol. 27, article no. 3374. https://doi.org/10.3390/molecules27113374

  109. Dragomanova, S., Lazarova, M., Munkuev, A., Suslov, E., Volcho, K., Salakhutdinov, N., Bibi, A., Reynisson, J., Tzvetanova, E., Alexandrova, A., Georgieva, A., Uzunova, D., Stefanova, M., Kalfin, R., and Tancheva, L., Molecules, 2022, vol. 27, article no. 5456, https://doi.org/10.3390/molecules27175456

  110. Munkuev, A.A., Mozhaitsev, E.S., Chepanova, A.A., Suslov, E.V., Korchagina, D.V., Zakharova, O.D., Ilina, E.S., Dyrkheeva, N.S., Zakharenko, A.L., Reynisson, J., Volcho, K.P., Salakhutdinov, N.F., and Lavrik, O.I., Molecules, 2021, vol. 26, article no. 3128, https://doi.org/10.3390/molecules26113128

  111. Suslov, E.V., Ponomarev, K.Yu., Volcho, K.P., and Salakhutdinov, N.F., Russ. J. Bioorg. Chem., 2021, vol. 47, p. 1133. https://doi.org/10.1134/S1068162021060236

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  112. Filatova, E.A., Pozharskii, A.F., Gulevskaya, A.V., Ozeryanskii, V.A., Tsybulin, S.V., and Filarowski, A., Eur. J. Org. Chem., 2019, vol. 2019, no. 42, p. 7128. https://doi.org/10.1002/ejoc.201901292

    Article  CAS  Google Scholar 

  113. Filatova, E.A., Tsybulin, S.V., Rybin, D.A., Ozeryan­skii, V.A., Gulevskaya, A.V., Pozharskii, A.F., and Borodkin, G.S., New. J. Chem., 2022, vol. 46, p. 1829. https://doi.org/10.1039/D1NJ05350G

    Article  CAS  Google Scholar 

  114. Khramchikhin, A.V., Skryl’nikova, M.A., Esaulko­va, I.L., Sinegubova, E.O., Zarubaev, V.V., Gureev, M.A., Puzyk, A.M., and Ostrovskii, V.A., Molecules, 2022, vol. 27, article no. 7940. https://doi.org/10.3390/molecules27227940

  115. Gurenkova, Yu.S., Kornyakov, I.V., Ostrovsky, V.A., Skrylnikova, M.A., and Khramchikhin, A.V., Russ. J. Gen. Chem., 2020, vol. 90, p. 1202. https://doi.org/10.1134/S1070363220070051

    Article  CAS  Google Scholar 

  116. Chikunova, E.I., Dar’in, D.V., Kukushkin, V.Yu., and Dubovtsev, A.Yu., Adv. Synth. Catal., 2022, vol. 364, p. 3697. https://doi.org/10.1002/adsc.202200751

    Article  CAS  Google Scholar 

  117. Shabalin, D.A., Kazak, M.K., Ushakov, I.A., Vashchenko, A.V., and Schmidt, E.Yu., J. Org. Chem., 2022, vol. 87, p. 6860. https://doi.org/10.1021/acs.joc.2c00555

    Article  CAS  PubMed  Google Scholar 

  118. Burykina, J.V., Shlapakov, N.S., Gordeev, E.G., König, B., and Ananikov, V.P., Chem. Sci., 2020, vol. 37, p. 10061. https://doi.org/10.1039/D0SC01939A

    Article  Google Scholar 

  119. Burykina, J.V., Kobelev, A.D., Shlapakov, N.S., Kostyukovich, A.Yu., Fakhrutdinov, A.N., König, B., and Ananikov, V.P., Angew. Chem., Int. Ed., 2022, vol. 61, article ID e202116888. https://doi.org/10.1002/anie.202116888

Download references

Funding

The All-Russian conference with international participation “Ideas and Legacy of A.E. Favorsky in Organic Chemistry” was held under financial support from St. Petersburg State University.

Author information

Authors and Affiliations

  1. Institute of Chemistry, St. Petersburg State University, 199034, St. Petersburg, Russia

    M. M. Efremova & N. V. Rostovskii

Authors
  1. M. M. Efremova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. V. Rostovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. V. Rostovskii.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 12, pp. 1525–1548 https://doi.org/10.31857/S0514749223120017.

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

This review is based on the reports presented at the All-Russian conference with international participation “Ideas and Legacy of A.E. Favorsky in Organic Chemistry,” which was held on July 3–6, 2023 in St. Petersburg. In commemoration of the 300th anniversary of St. Petersburg State University.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Efremova, M.M., Rostovskii, N.V. Symposium on the Chemistry of Alkynes, Allenes, and Small Rings. Russ J Org Chem 59, 2015–2037 (2023). https://doi.org/10.1134/S1070428023120011

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428023120011

Keywords:

Search

Navigation