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DOI: 10.1055/a-2501-3442
Photocatalytic defluorinative borylation of α-trifluoromethyl-styrenes
Supported by: H2020 Marie Skłodowska-Curie Actions 101102819
The defluorinative radical borylation of α-trifluoromethyl-styrenes described here shows the novel access to difluoroalkene-aminoboranes, with its application demonstrated by the diverse substrate scope synthesized in good yields. Use of borobetaine as the boryl radical precursor allows the formation of the key boryl radical, which is involved in the initial C–B bond formation with α-trifluoromethyl-styrenes. A radical-polar crossover mechanism releasing fluoride provides the difluoroalkene product bearing the aminoborane synthetic handle. The interest to access the difluoroalkene motif stems from their use as potent carbonyl bioisosteres, shown to enhance biological activity and reactivity. Presence of the aminoborane moiety further allows functionalization such as Suzuki-Miyaura cross-coupling of the borylated products, which is demonstrated using complex aryl bromides. Further we have shown various post-functionalizations, demonstrating difluoroalkene-aminoboranes to be valuable building blocks for the construction of complex, high-value molecules.
Publication History
Received: 25 September 2024
Accepted after revision: 28 November 2024
Accepted Manuscript online:
12 December 2024
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