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A Borrowing Hydrogen Strategy for Dehydrative Coupling of Aminoisoquinolines with Benzyl Alcohols in Water
We report a borrowing hydrogen strategy for a palladium-catalyzed dehydrative coupling of aminoisoquinolines with benzylic alcohols in water. This cascade reaction using the pi-benzylpalladium system can be achieved in an atom-economic process without the need for base or other additives, furnishing the N-benzylated aminoisoquinolines in moderate to excellent yields along with water as the sole co-product. The crossover experiment using [D7]benzyl alcohol and 4-methoxybenzyl alcohol afforded H/D scrambled products. KIE experiments showed that benzylic C?H bond cleavage of benzyl alcohol was involved in the turnover limiting step (KIE = 4.4). The coupling reaction was found to be first order in benzyl alcohol with a kinetic solvent isotope effect (KSIE) of 1.6. These experimental results are consistent with a borrowing hydrogen mechanism in water. Notably, the water-soluble Pd0/TPPMS system can be applied to the more challenging catalytic benzylic amination with aminoisoquinoline nucleophiles despite the possible deactivation of PdII species.
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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem