Premium
Gold‐Catalyzed Cycloaromatization of 2,4‐Dien‐6‐yne Carboxylic Acids: Synthesis of 2,3‐Disubstituted Phenols and Unsymmetrical Bi‐ and Terphenyls
Author(s) -
GarcíaGarcía Patricia,
FernándezRodríguez Manuel A.,
Aguilar Enrique
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901269
Subject(s) - decarboxylation , regioselectivity , phenols , catalysis , chemistry , sequence (biology) , organic chemistry , biochemistry
Round numbers : A gold‐catalyzed 2,7‐cycloaromatization of captodative dienyne carboxylic acids has been developed that occurs at room temperature with low catalyst loading and total regioselective control (see scheme). The reaction is totally dependent on the electronic properties of the dienyne acid: if a strong electron‐donating group is not directly linked to the triple bond, a 1,6‐cyclization/decarboxylation sequence takes place.