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Metal‐Free One‐Pot Synthesis of Benzofurans
Author(s) -
Ghosh Raju,
Stridfeldt Elin,
Olofsson Berit
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403523
Subject(s) - reagent , oxime , yield (engineering) , chemistry , in situ , transition metal , metal , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
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.