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Communication | Special issue | Vol 95, No. 2, 2017, pp.738-747
Published online, 16th January, 2017
DOI: 10.3987/COM-16-S(S)73
α-Functionalization of Tetrahydroisoquinolines with Activated Alkyl Bromide under Photoredox Catalysis

Takafumi Ide, Kazunori Shimizu, Yuji Kawato, Hiromichi Egami, and Yoshitaka Hamashima*

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan


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 α-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.