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

ABSTRACT: 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.

SUBMITTER: Stammers E

PROVIDER: S-EPMC10382484 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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

Stammers Ellie E Parsons Chris D CD Clayden Jonathan J Lennox Alastair J J AJJ

Nature communications 20230728 1

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 ...[more]

PMID: 37507363

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