Varinder K. Aggarwal
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 |
Files
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Publisher Licence URL
https://creativecommons.org/licenses/by/4.0/
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