Tetrafluoroboric Acid

Friestad, Gregory K.; Branchaud, Bruce P.

doi:10.1002/047084289x.rt035

Cited by 4 publications

(2 citation statements)

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“…A review of the literature revealed various applications of tetrafluoroboric acid, including Hosomi-Sakurai allylation and Prins cyclization, 32 cycloisomerizations, 33 polycyclizations, 34 syntheses of diarylmethyl tetrafluoroborates, 35 Fischer indole synthesis, 36 Meyer-Schuster-like rearrangement, 37 ring closures of aryl C-glycosides, 38 the cross-coupling of trifluoroborates with benzhydryl alcohols, 39 and more. 40 Due to the lack of prior attempts to use the tetrafluoroboric acid-diethyl ether complex for the dehydration of alcohols, we studied the behavior of commonly available alcohols in the presence of the tetrafluoroboric acid-diethyl ether complex. The optimized reaction conditions for the dehydration of halocyclobutanols were used to synthesize 1,2-diphenylcyclobutene 9a in a 53% yield (Scheme 3).…”

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confidence: 99%

Halocyclobutanol Dehydration En Route to Halocyclobutenes

et al. 2022

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Section: Accepted Manuscriptmentioning

confidence: 99%

Halocyclobutanol Dehydration En Route to Halocyclobutenes

et al. 2022

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“…a NMR yield using 1,1,2,2-tetrachloroethane as the internal standard. b Based on the Evans p K a table except HSbF 6 and HBF 4 …”

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Rapid Access to Kinase Inhibitor Pharmacophores by Regioselective C–H Arylation of Thieno[2,3-d]pyrimidine

et al. 2020

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Regioselective C–H arylations of thieno[2,3-d]pyrimidine are accomplished under palladium catalysis. Thieno[2,3-d]pyrimidines react with aryl iodides at the C6-position and with aryl boronic acids at the C5-position, showing excellent regioselectivity. Mechanistic investigations indicate that the regioselectivity is controlled by the nature of the palladium catalyst: the cationic palladium favorably arylates the C5-position. The utility of this direct arylation has been highlighted in the streamlined synthesis of kinase inhibitors and their derivatives.

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