We have developed a method for the site-selective hydrogenation of unactivated alkenes using 8-aminoquinoline amide as the directing group. For unactivated alkenes with two C-C double bonds, Daugulis's 8-aminoquinoline amide facilitated the site-selective hydrogenation of the desired C-C double bond, producing a product in which one C-C double bond was reduced. Site-selective reduction methodologies using intramolecular directing groups are expected to contribute significantly to the synthesis of molecules with multiple reducible functional groups in the future.
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