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Reductive Cyclization of Bromoenynamides with Alcohols as Hydride Source: Synthesis and Reactions of 2‐Amidodienes
Author(s) -
Greenaway Rebecca L.,
Campbell Craig D.,
Chapman Helen A.,
Anderson Edward A.
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200703
Subject(s) - chemistry , alkyne , hydride , alcohol , aryne , palladium , catalysis , selectivity , combinatorial chemistry , organic chemistry , medicinal chemistry , hydrogen
Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium‐catalyzed cyclization to cyclic 2‐amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5–8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi‐ and tricyclic azacycles, which can be further oxidized to the aromatic azacycles.