Synthesis of 2-alkyl-2-boryl-substituted-tetrahydrofurans via copper(i)-catalysed borylative cyclization of aliphatic ketones.


Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido, Japan. [Email]


A new method was developed for synthesizing 2-alkyl-2-boryl-tetrahydrofuran derivatives from aliphatic ketones using a copper(i)/N-heterocyclic carbene complex catalyst. This reaction presumably proceeds through the nucleophilic addition of a borylcopper(i) intermediate to ketone, followed by intramolecular substitution of the resulting alkoxide for the halide leaving group. The new borylation products, 2-alkyl-2-boryl-tetrahydrofuran derivatives with a condensed structure around the C-B bond, cannot be synthesized by other methods.

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