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.
Keywords:
furan, CH-alkylation, palladium, photoinduced metal catalysis, 2-hetarylfurans.
Citation:
I. V. Lavrentev, K. E. Shepelenko, I. G. Gnatiuk, A. A. Aleksandrov, Y. Zhang, V. M. Chernyshev, “CH-alkylation of furan derivatives under photoinduced Pd catalysis”, Mendeleev Commun., 33:4 (2023), 494–496
Linking options:
https://www.mathnet.ru/eng/mendc438
https://www.mathnet.ru/eng/mendc/v33/i4/p494
This publication is cited in the following 5 articles:
Ilya M. Tkachenko, Natalia A. Ivanova, Kristina S. Khrapovitskaya, Yuri N. Klimochkin, “Synthesis of Alkylated Carbonyl‐Bearing Furans via Acid‐Catalyzed Friedel‐Crafts Reaction”, Asian J Org Chem, 2024
Petter Dunås, Andrew J. Paterson, Simon E. Lewis, Nina Kann, “Carbon–carbon bond formation using aromatics from biomass”, Chem. Commun., 2024
Konstantin E. Shepelenko, Irina G. Gnatiuk, Igor V. Lavrentev, Mikhail E. Minyaev, Victor M. Chernyshev, Valentine P. Ananikov, “Simple Access to 3-(Hetero)arylated Derivatives of 2-Furoic Acid via Ru(II)-Catalyzed C3-H Arylation of 2-Furoylimidazole”, Synthesis, 56:19 (2024), 3063
A. V. Astakhov, Yu. N. Tkachenko, I. V. Lavrentev, D. V. Pasyukov, M. A. Shevchenko, V. M. Chernyshev, “Transition metal-free visible light induced intramolecular C–Hal/C–H bond activation leading to cyclization into pyrimido[5′,4′:3,4]pyrrolo[1,2-f ]phenanthridines”, Mendeleev Commun., 34:2 (2024), 238–241
K. E. Shepelenko, I. G. Gnatiuk, V. M. Chernyshev, “Ruthenium-catalyzed C3 Alkylation of the Furan/Thiophene Ring in 2-(Furan-2-carbonyl)/(Thiophene-2-carbonyl)-1-methylimidazoles with Acrylic Acid Derivatives”, Russ J Org Chem, 60:11 (2024), 2140
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