Synthesis 2024; 56(19): 3063-3073
DOI: 10.1055/s-0043-1775383
paper

Simple Access to 3-(Hetero)arylated Derivatives of 2-Furoic Acid via Ru(II)-Catalyzed C3-H Arylation of 2-Furoylimidazole

Konstantin E. Shepelenko
a   Platov South-Russian State Polytechnic University, 346428 Novocherkassk, Russian Federation
,
Irina G. Gnatiuk
a   Platov South-Russian State Polytechnic University, 346428 Novocherkassk, Russian Federation
,
Igor V. Lavrentev
a   Platov South-Russian State Polytechnic University, 346428 Novocherkassk, Russian Federation
,
Mikhail E. Minyaev
b   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
,
Victor M. Chernyshev
a   Platov South-Russian State Polytechnic University, 346428 Novocherkassk, Russian Federation
,
a   Platov South-Russian State Polytechnic University, 346428 Novocherkassk, Russian Federation
b   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
› Author Affiliations
This work was supported by the Russian Science Foundation (grant no. 23-73-10129, https://rscf.ru/project/23-73-10129/).


Abstract

A new approach for the preparation of a variety of 3-arylated 2-furoic acid derivatives has been developed. The approach involves selective Ru-catalyzed C3-H arylation of the furan moiety of readily available 2-furoyl-1-methylimidazole (using imidazole as a removable N-donor directing group), subsequent N-methylation, and nucleophilic substitution of the imidazole moiety with N, O, S, and C nucleophiles.

Supporting Information



Publication History

Received: 16 April 2024

Accepted after revision: 21 June 2024

Article published online:
16 July 2024

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