Palladium-Catalyzed Direct Heck Arylation of Dual π-Deficient/π-Excessive Heteroaromatics. Synthesis of C-5 Arylated Imidazo[1,5-a]pyrazines
Organic Letters2008Vol. 10(14), pp. 2923–2926
Citations Over TimeTop 10% of 2008 papers
Jianxin Wang, J. Adam McCubbin, Meizhong Jin, Radoslaw S. Laufer, Yunyu Mao, Andrew P. Crew, Mark J. Mulvihill, Victor Snieckus
Abstract
A general and efficient synthesis of 5-aryl imidazo[1,5- a]pyrazines by palladium-catalyzed coupling of the corresponding 8-substituted derivatives with aryl halides is described. The scope of this new reaction for the imidazo[1,5- a]pyrazine ring system was explored using three readily available 8-substituted precursors, X = NH2, NMe2, and OMe, as well as 8-aryl derivatives, X = Ar'. On the basis of these results as well as studies using a deuterated derivative, a Heck-like mechanism is proposed for this transformation.
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