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[Report] Arylation of hydrocarbons enabled by organosilicon reagents and weakly coordinating anions

ScienceNOW - Fetched: March 31st, 2017, 3:00pm UTC

Over the past 80 years, phenyl cation intermediates have been implicated in a variety of C–H arylation reactions. Although these examples have inspired several theoretical and mechanistic studies, aryl cation equivalents have received limited attention in organic methodology. Their high-energy, promiscuous reactivity profiles have hampered applications in selective intermolecular processes. We report a reaction design that overcomes these challenges. Specifically, we found that β-silicon–stabilized aryl cation equivalents, generated via silylium-mediated fluoride activation, undergo insertion into sp3 and sp2 C–H bonds. This reaction manifold provides a framework for the catalytic arylation of hydrocarbons, including simple alkanes such as methane. This process uses low loadings of Earth-abundant initiators (1 to 5 mole percent) and occurs under mild conditions (30° to 100°C). Authors: Brian Shao, Alex L. Bagdasarian, Stasik Popov, Hosea M. Nelson

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