An expedient route to substituted furans via olefin cross-metathesis.
The olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di- or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.
Department of Chemistry, University of Oxford, Oxford, OX1 3TA UK. timothy.donohoe@chem.ox.ac.uk
Timothy J
TJ
Donohoe
John F
JF
Bower
D000475:Alkenes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*
D000475:Alkenes; D005663:Furans