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alpha-Functionalization of tetrahydroisoquinolines with activated alkyl bromide under photoredox catalysis
Benzylic C-H functionalization of N-aryl-tetrahydroisoquinolines (THIQs) with various benzyl bromides was developed using a photoredox iridium (Ir) catalyst under blue LED irradiation, affording arylmethyl group-substituted THIQs in moderate to good yields (up to 82%). This photoredox catalyst-mediated reaction was also applicable to other activated bromides, including allyl bromide, cinnamyl bromide, propargyl bromide, and alpha-bromoacetate. We propose that photoredox catalyst-mediated electron transfer generates a radical species from the THIQ and another radical from the bromide, and then radical-radical cross-coupling occurs to form a new carbon-carbon bond.
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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem