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Gold‐Catalyzed Sequential Activation of Propargylic Carboxylates: A Facile Route to Benzoannulenes
Author(s) -
Oh Chang Ho,
Kim Ji Hee,
Oh Bu Keun,
Park Jong Ryul,
Lee Ji Ho
Publication year - 2013
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.201204091
Subject(s) - catalysis , annulene , cascade , chemistry , hydrolysis , combinatorial chemistry , medicinal chemistry , organic chemistry , chromatography
A cascade reaction of 1‐(2‐(3‐acetoxyprop‐1‐ynyl)phenyl)prop‐2‐ynyl acetate and its derivatives is catalyzed by gold to give the corresponding benzo[7]annulenes (see scheme) in excellent yields. A double activation of the gold catalyst toward two different propargylic carboxylates was proposed. Benzoannulenes were hydrolyzed to 8‐hydroxybenzo[7]annulene‐5‐ones.