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Complete Switch of Selectivity in the C–H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups

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posted on 28.10.2015, 00:00 by Jiyu Kim, Sung-Woo Park, Mu-Hyun Baik, Sukbok Chang
A complete switch in the Cp*Ir­(III)-catalyzed paths between C–H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the β-H elimination, which ultimately affords the observed chemoselectivity.

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