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

Ellie Stammers, Chris D. Parsons, Jonathan Clayden*, Alastair J J Lennox*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)

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.
Original languageEnglish
Article number4561
JournalNature Communications
Volume14
Issue number1
DOIs
Publication statusPublished - 28 Jul 2023

Bibliographical note

Funding Information:
The authors acknowledge funding from the Royal Society (University Research Fellowship and Enhancement Awards to A.J.J.L.), the ERC (Advanced Grant 883789 to J.C.), EPSRC (EP/S018050/1 and EP/L015366/1) and AstraZeneca for a studentship (to E.S.) through the Bristol Centre for Doctoral Training in Chemical Synthesis.

Publisher Copyright:
© 2023, The Author(s).

Structured keywords

  • BCS and TECS CDTs

Fingerprint

Dive into the research topics of 'Electrochemical synthesis of biaryls by reductive extrusion from N,N’-diarylureas'. Together they form a unique fingerprint.

Cite this