Journal
ORGANIC LETTERS
Volume 10, Issue 13, Pages 2633-2636Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol800509z
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A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or anti-Wacker-type oxidative addition to the Pd-0 catalyst.
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