Control of regioselectivity in palladium-catalyzed arene C�H functionalization is typically accomplished with directing groups that lead to ortho-functionalization. A new approach, pioneered by the Jin-Quan Yu lab, employs nitrile-containing templates to achieve remote meta-selectivity. We present a computational study of the mechanism and origins of regioselectivity in template-directed C�H olefination reactions, highlighting the role of template conformation and distortion energy. This analysis is applied toward developing a strategy for de novo template design.

Origins of regioselectivity in template-directed palladium-catalyzed C�H bond activation

247th National Meeting (2014)

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