Reductive Cyclization of Bromoenynamides with Alcohols as Hydride Source: Synthesis and Reactions of 2‐Amidodienes

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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.

Document Type: Communications


Affiliations: 1: Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, U.K. phone: (+44)-1865-285-037, Fax: (+44)-1865-285-002 2: Syngenta Ltd., Jealott's Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, U.K.

Publication date: November 26, 2012

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