Keywords
2-hetarylfurans.
CH-alkylation
furan
palladium
photoinduced metal catalysis
Abstract
A new method for selective C(5)-H alkylation of 2-substituted furans with tertiary and secondary alkyl bromides under photoinduced by visible light (∼460 nm) palladium catalysis has been developed. The method is relied on the use of available Pd(PPh3)4 catalyst under mild conditions (30 ± 5 °C, K2CO3 as base), tolerates to various functional groups in furanic substrates and provides from good to excellent yields of alkylated products.
References
.
Karlinskii B.Y., Ananikov V.P.
ChemSusChem,
2020
.
Kucherov F.A., Romashov L.V., Galkin K.I., Ananikov V.P.
ACS Sustainable Chemistry and Engineering,
2018
.
Chernyshev V.M., Kravchenko O.A., Ananikov V.P.
Russian Chemical Reviews,
2017
.
Kashparova V.P., Chernysheva D.V., Klushin V.A., Andreeva V.E., Kravchenko O.A., Smirnova N.V.
Russian Chemical Reviews,
2021
.
Chacón‐Huete F., Messina C., Cigana B., Forgione P.
ChemSusChem,
2022
.
Mori A., Curpanen S., Pezzetta C., Perez‐Luna A., Poli G., Oble J.
European Journal of Organic Chemistry,
2022
.
Chernyshev V.M., Khazipov O.V., Eremin D.B., Denisova E.A., Ananikov V.P.
Coordination Chemistry Reviews,
2021
.
Evano G., Theunissen C.
Angewandte Chemie - International Edition,
2019
.
Cheung K.P., Sarkar S., Gevorgyan V.
Chemical Reviews,
2021
.
Chuentragool P., Kurandina D., Gevorgyan V.
Angewandte Chemie - International Edition,
2019
.
Lee G.S., Kim D., Hong S.H.
Nature Communications,
2021
.
Zhou W., Cao G., Zhang Z., Yu D.
Chemistry Letters,
2019
.
Khazipov O.V., Shepelenko K.E., Pasyukov D.V., Chesnokov V.V., Soliev S.B., Chernyshev V.M., Ananikov V.P.
Organic Chemistry Frontiers,
2021
.
Schramm Y., Takeuchi M., Semba K., Nakao Y., Hartwig J.F.
Journal of the American Chemical Society,
2015
.
Makarov A.S., Kekhvaeva A.E., Hall C.J., Price D.R., Trushkov I.V., Uchuskin M.G.
Tetrahedron,
2017
.
Fu Y., Shang R., Wang G.
Synthesis,
2018
.
Racané L., Zlatar I., Perin N., Cindrić M., Radovanović V., Banjanac M., Shanmugam S., Stojković M.R., Brajša K., Hranjec M.
Molecules,
2021
.
Howell B.A., Lazar S.T.
Industrial & Engineering Chemistry Research,
2018
.
Luo W., Yang Y., Liu B., Yin B.
Journal of Organic Chemistry,
2020
.
Ankade S.B., Shabade A.B., Soni V., Punji B.
ACS Catalysis,
2021
.
Zhou W., Cao G., Shen G., Zhu X., Gui Y., Ye J., Sun L., Liao L., Li J., Yu D.
Angewandte Chemie - International Edition,
2017
.
Aleksandrov A.A., Savost’yanov A.P., El’chaninov M.M., Salamatina G.V.
Russian Journal of General Chemistry,
2011
.
Elchaninov M.M., Aleksandrov A.A.
Russian Journal of Organic Chemistry,
2018
.
Climent M.J., Corma A., Iborra S.
Green Chemistry,
2014
.
Theunissen C., Wang J., Evano G.
Chemical Science,
2017
.
Yuan J., Zhang X., Yang C.
RSC Advances,
2021
.
Jaswal A., Singh P.P., Mondal T.
Green Chemistry,
2022
.
Kim D., Lee G.S., Kim D., Hong S.H.
Nature Communications,
2020
.
Ferreira M.A., Paixão M.W., Jardim G.A., Dantas J.A., Barboza A.A.
Synthesis,
2022
.
Iovel' I.G., Lukevics E.
Chemistry of Heterocyclic Compounds,
1998
.
Karlinskii B.Y., Ananikov V.P.
Chemical Society Reviews,
2023
.
Manna S.K., Giri S., Mondal S., Sana R.N., Samal A.K., Mandal A.
ChemistrySelect,
2023
.
Wu X., See J.W., Xu K., Hirao H., Roger J., Hierso J., Zhou J.S.
Angewandte Chemie - International Edition,
2014
.
Temirak A., Shaker Y.M., Ragab F.A., Ali M.M., Ali H.I., El Diwani H.I.
European Journal of Medicinal Chemistry,
2014
.
Wang C., Gong M., Huang M., Li Y., Kim J.K., Wu Y.
Tetrahedron,
2016
.
Abdullaziz M.A., Abdel-Mohsen H.T., El Kerdawy A.M., Ragab F.A., Ali M.M., Abu-bakr S.M., Girgis A.S., El Diwani H.I.
European Journal of Medicinal Chemistry,
2017
.
Nakagawa Y., Tamura M., Tomishige K.
Fuel Processing Technology,
2019
.
Liu Z., Chen X.
Chem,
2020
.
Shepelenko K.E., Nikolaeva K.A., Gnatiuk I.G., Garanzha O.G., Alexandrov A.A., Minyaev M.E., Chernyshev V.M.
Mendeleev Communications,
2022