Regio- and Diastereoselective Decarboxylative Coupling of Heteroaromatic Alkanes
Journal of the American Chemical Society2007Vol. 129(14), pp. 4138–4139
Citations Over TimeTop 10% of 2007 papers
Abstract
Allylic esters of heteroaromatic alkanes undergo facile palladium-catalyzed decarboxylative coupling. The resulting C−C bond is formed with high diastereoselectivity and high regioselectivity for coupling at the more substituted allyl terminus. It is proposed that this unusual combination of selectivities results from a tandem allylation/aza-Cope rearrangement sequence. After allylation, decarboxylative dearomatization produces an intermediate for the aza-Cope rearrangement. The subsequent aza-Cope rearrangement occurs under mild conditions because it is driven by rearomatization.
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