Elsevier

Tetrahedron Letters

Volume 38, Issue 25, 23 June 1997, Pages 4393-4396
Tetrahedron Letters

Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium

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Abstract

Potassium aryl- and alkenyltrifluoroborates react smoothly with arenediazonium tetrafluoroborates under mild conditions in the presence of a palladium catalyst and without added base.

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    The boronic acid was prepared by hydroboration of 1-decene with dibromoborane dimethyl sulfide with 5 mol% tribromoborane, then hydrolyzed to give the n-decylboronic acid [24]. Fluoridation reaction conditions were based on the methods reported by Vedejs [25] and Genêt [26]. Decylboronic acid was first dissolved in methanol then a concentrated aqueous solution of the KHF2 was then added to the open flask, resulting in an immediate formation of a thick slurry.

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