Metal‐Free One‐Pot Synthesis of Benzofurans. Issue 29 (20th June 2014)

• Record Type: Journal Article
• Authors: Ghosh, Raju; Stridfeldt, Elin; Olofsson, Berit
• Is Part Of: Chemistry. Volume 20:Issue 29(2014)
• Page Start: 8888
• Page End: 8892
• Publication Date: 2014-06-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201403523
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition‐metal‐free conditions. The obtained <italic>O</italic>‐arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[<italic>b</italic>]furans through oxime formation, [3, 3]‐rearrangement, and cyclization in a fast and operationally simple one‐pot fashion without using excess reagents. Alternatively, the <italic>O</italic>‐arylated products could be isolated or transformed in situ to aryloxyamines or <italic>O</italic>‐arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)‐machaeriol B.</p> </abstract>