Electrochemical synthesis of biaryls by reductive extrusion from N,N'-diarylureas.

Autor: Stammers E; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK., Parsons CD; Early Chemical Development, Pharmaceutical Sciences, R&D, AstraZeneca, Macclesfield, SK10 2NA, UK., Clayden J; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. j.clayden@bristol.ac.uk., Lennox AJJ; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. a.lennox@bristol.ac.uk.
Jazyk: angličtina
Zdroj: Nature communications [Nat Commun] 2023 Jul 28; Vol. 14 (1), pp. 4561. Date of Electronic Publication: 2023 Jul 28.
DOI: 10.1038/s41467-023-40237-6
Abstrakt: The synthesis of biaryl compounds by the transition-metal free coupling of arenes is an important contemporary challenge, aiming to avoid the toxicity and cost profiles associated with the metal catalysts commonly used in the synthesis of these pharmaceutically relevant motifs. In this paper, we describe an electrochemical approach to the synthesis of biaryls in which aniline derivatives are coupled through the formation and reduction of a temporary urea linkage. The conformational alignment of the arenes in the N,N'-diaryl urea intermediates promotes C-C bond formation following single-electron reduction. Our optimized conditions are suitable for the synthesis of a variety of biaryls, including sterically hindered examples carrying ortho-substituents, representing complementary reactivity to most metal catalysed methods.
(© 2023. The Author(s).)
Databáze: MEDLINE
Externí odkaz: