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Free keywords:
DEHYDROGENATIVE COUPLING REACTION; CARBON-HYDROGEN BONDS; TERTIARY-AMINES; NITROGEN ATOM; OXIDATIVE CYANATION; SODIUM-CYANIDE; ADJACENT; NUCLEOPHILICITY; AMIDOALKYLATION; ALKYNYLATION
Abstract:
An organocatalytic oxidative synthesis of N-protected tetrahydroisoquinolines is described by C–H functionalization via intermediate peroxides. The peroxides were synthesized from tert-butylhydroperoxide under metal-free thermal conditions and were converted into the final products by Brønsted acid catalyzed substitution. The nucleophile scope was investigated in detail and proved to be broad; N-deprotection of the coupling products could also be achieved.