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

Organic & Biomolecular Chemistry Pub Date: 2019-05-20 DOI: 10.1039/C9OB00962K

Abstract

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.

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