2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans

Publication Type: Journal contribution (peer reviewed)
Authors: Schmidt, D.; Malakar, C. C.; Beifuss, U.
Year of publication: 2014
Published in: Org. Lett
Band/Volume: 16/
DOI: 10.1021/ol502371j
Page (from - to): 4862-4865

Abstract

The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with β-ketoesters and 1,3-diketones, respectively, in DMF at 120 °C using Cs₂CO₃ as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.

Involved persons

Prof. Dr. rer. nat. Uwe Beifuß

Involved institutions

Institute of Chemistry
Bioorganic Chemistry