Issue 14, 2016

Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes

Abstract

We describe the first ring-opening of furfuryl alcohols with boronic acids to afford functionalized γ-ketoaldehydes. The transformation builds a new C–C bond at the original C-4 of the starting furan, and tolerates ring-substitution at C-3 and C-4 positions. The reaction takes place under metal-free conditions by promotion with tartaric acid.

Graphical abstract: Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes

Supplementary files

Article information

Article type
Communication
Submitted
23 Oct 2015
Accepted
15 Jan 2016
First published
15 Jan 2016

Chem. Commun., 2016,52, 3018-3021

Author version available

Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes

S. Roscales and A. G. Csákÿ, Chem. Commun., 2016, 52, 3018 DOI: 10.1039/C5CC08809G

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