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Allylboronates are unique building blocks widely used in organic synthesis, but the construction of cyclic allylboranates remains a challenging subject. We demonstrate here a mild and efficient access to this… Click to show full abstract
Allylboronates are unique building blocks widely used in organic synthesis, but the construction of cyclic allylboranates remains a challenging subject. We demonstrate here a mild and efficient access to this type of compound through the cross-electrophile coupling of vinyl triflates and α-chloroboronates. The reaction proceeded with a good substrate scope and good functional group compatibility. The ready availability of vinyl triflates from ketones, as well as the rich chemistry of allylboranates, makes our method suitable for the divergent modification of biologically active compounds. Preliminary mechanistic studies revealed that α-chloroboronates were activated via a radical process.
Journal Title: Organic letters
Year Published: 2020
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