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Facile N-directed Ru-catalyzed C(3)–H acylation of heterocyclopentadienes with acyl chlorides Full article

Journal Organic Chemistry Frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129
Output data Year: 2025, Volume: 12, Number: 24, Pages: 6864-6872 Pages count : 9 DOI: 10.1039/d5qo00965k
Authors Shepelenko Konstantin E. 1,2 , Gnatiuk Irina G. 1,2 , Aleksandrov Andrey A. 2 , Minyaev Mikhayl E. 3 , Chernyshev Victor M. 1,2 , Ananikov Valentine P. 3
Affiliations
1 Platov South-Russian State Polytechnic University (NPI), 346428, Novocherkassk, Prosveshcheniya st., 132, Russian Federation
2 Skolkovo Institute of Science and Technology, Build. 1, 30 Bol′shoy b-r, Skolkovo Innovation Center, 121205 Moscow, Russian Federation
3 Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russian Federation

Abstract: The selective C3–H functionalization of 2-substituted heterocyclopentadienes (furan, thiophene and pyrrole) remains challenging owing to the typically higher reactivity of the C5–H and C4–H bonds. In this study, we report a facile method for the selective C3–H acylation of pharmaceutically and agrochemically relevant heterocyclopentadienes bearing N-donor directing groups at the 2-position. This approach utilizes readily available aliphatic, aromatic and heteroaromatic acyl chlorides under catalysis by a Ru/PPh3 system generated in situ from commercially available, bench-stable precursors. The method exhibits broad tolerance toward various N-donor directing groups, including those with unprotected NH moieties potentially susceptible to N-acylation. Preliminary mechanistic studies suggest a reaction pathway involving C–H activation, which is rate-limiting and assisted by the carboxylate anion generated via the partial decomposition of the acyl chloride in a basic medium.
Cite: Shepelenko K.E. , Gnatiuk I.G. , Aleksandrov A.A. , Minyaev M.E. , Chernyshev V.M. , Ananikov V.P.
Facile N-directed Ru-catalyzed C(3)–H acylation of heterocyclopentadienes with acyl chlorides
Organic Chemistry Frontiers. 2025. V.12. N24. P.6864-6872. DOI: 10.1039/d5qo00965k WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001568216900001
Scopus: 2-s2.0-105018101180
OpenAlex: W4414017792
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