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DOI: 10.1055/a-2501-3442
Photocatalytic Defluorinative Borylation of α-(Trifluoromethyl)styrenes
C.S.B. thanks the Marie Curie Actions for a Fellowship (B-STRAIN 101102819).
For Tatì
Abstract
The defluorinative radical borylation of α-(trifluoromethyl)styrenes is a novel access to diverse difluoroalkene-aminoboranes in good yields. Using the boryl radical precursor borobetaine gives the key boryl radical that reacts with the α-(trifluoromethyl)styrene forming the initial C–B bond. Then a radical-polar crossover mechanism releases fluoride to provide a difluoroalkene product bearing the aminoborane synthetic handle. The difluoroalkene motif is of interest as a potent carbonyl bioisostere that has been shown to enhance biological activity and reactivity. The presence of the aminoborane moiety allows further functionalization such as Suzuki–Miyaura cross-coupling of the borylated products, which is demonstrated using complex aryl bromides. Various post-functionalizations demonstrate difluoroalkene-aminoboranes to be valuable building blocks for the construction of complex, high-value molecules.
Key word
boryl radicals - photoredox catalysis - radical-polar crossover - difluoroalkenes - borylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2501-3442.
- Supporting Information
Publication History
Received: 25 September 2024
Accepted after revision: 28 November 2024
Accepted Manuscript online:
12 December 2024
Article published online:
20 January 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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