Metal-Free One-Pot Synthesis of Benzofurans
2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 29, 8888-8892 p.Article in journal (Refereed) Published
Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B.
Place, publisher, year, edition, pages
2014. Vol. 20, no 29, 8888-8892 p.
arylation, aryloxyamines, cyclization, diaryliodonium salts, O-aryloximes, sigmatropic rearrangement
IdentifiersURN: urn:nbn:se:su:diva-106727DOI: 10.1002/chem.201403523ISI: 000339386700013OAI: oai:DiVA.org:su-106727DiVA: diva2:738416
FunderWenner-Gren FoundationsCarl Tryggers foundation , 12:345