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Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent

Kerr, William and Morrison, Angus J and Pazicky, Marek and Weber, Tina (2012) Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent. Organic Letters, 14 (9). pp. 2250-2253. ISSN 1523-7060

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Abstract

Bismesitylmagnesium has been shown to successfully mediate the Shapiro reaction. A range of tosylhydrazones has been subjected to the developed system, which furnishes exceptionally high incorporation of the introduced electrophiles and good yields of the functionalised styrenes. At conveniently accessible temperatures and with a comparably small excess of base reagent, this protocol offers an efficient alternative to the lithium-mediated process. Importantly, 1.05 equiv of Weinreb amides are sufficient to obtain aryl enones in good yields.