Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes

Aggarwal, Varinder K.; Silvi, Mattia; Sandford, Christopher

Abstract

© 2017 American Chemical Society. Vinyl boronates react with electron-deficient alkyl iodides in the presence of visible light to give boronic esters in which two new C-C bonds have been created. The reaction occurs by radical addition of an electron-deficient alkyl radical to the vinyl boronate followed by electron transfer with another molecule of alkyl iodide, continuing the chain, and triggering a 1,2-metalate rearrangement. In a number of cases, the use of a photoredox catalyst enhances yields significantly. The scope of the radical precursor includes α-iodo ketones, esters, nitriles, primary amides, α-fluorinated halo-acetates and perfluoroalkyl iodides.

Citation

Aggarwal, V. K., Silvi, M., & Sandford, C. (2017). Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes. Journal of the American Chemical Society, 139(16), 5736-5739. https://doi.org/10.1021/jacs.7b02569

• Journal Article Type: Article
• Acceptance Date: Apr 17, 2017
• Online Publication Date: Apr 17, 2017
• Publication Date: Apr 26, 2017
• Deposit Date: Jan 29, 2020
• Publicly Available Date: Feb 3, 2020
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 139
• Issue: 16
• Pages: 5736-5739
• DOI: https://doi.org/10.1021/jacs.7b02569
• Public URL: https://nottingham-repository.worktribe.com/output/3826705
• Publisher URL: https://pubs.acs.org/doi/10.1021/jacs.7b02569