Iterative One-Carbon Homologation of Unmodified Carboxylic Acids

Wheatley, Emilie; Melnychenko, Heorhii; Silvi, Mattia

Abstract

The one-carbon homologation of carboxylic acids is a valuable route to construct families of homologues, which play fundamental roles in chemistry and biology. However, known procedures are based on multistep sequences, use harsh conditions or are limited in scope. Thus, almost a century after the discovery of the original Arndt–Eistert homologation sequence, a general method to directly convert carboxylic acids into their corresponding homologues remains elusive. Exploiting the photoredox reactivity of nitroethylene, we disclose a practical visible-light-induced homologation of unmodified carboxylic acids. Iterations of the procedure reveal an exceptionally tunable strategy for the construction of inert carbon spacers, opening new opportunities in synthesis.

Citation

Wheatley, E., Melnychenko, H., & Silvi, M. (2024). Iterative One-Carbon Homologation of Unmodified Carboxylic Acids. Journal of the American Chemical Society, https://doi.org/10.1021/jacs.4c13630

• Journal Article Type: Article
• Acceptance Date: Dec 6, 2024
• Online Publication Date: Dec 10, 2024
• Publication Date: Dec 10, 2024
• Deposit Date: Dec 17, 2024
• Publicly Available Date: Dec 17, 2024
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• DOI: https://doi.org/10.1021/jacs.4c13630
• Public URL: https://nottingham-repository.worktribe.com/output/42841043
• Publisher URL: https://pubs.acs.org/doi/10.1021/jacs.4c13630