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Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes

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journal contribution
posted on 25.07.2017, 00:00 by Tianyu Huang, Xiaohua Liu, Jiawen Lang, Jian Xu, Lili Lin, Xiaoming Feng
An efficient asymmetric aerobic oxidation of tetrahydroisoquinolines with terminal alkynes was realized under mild reaction conditions using O2 as the sole oxidant. A chiral N,N′-dioxide/zinc­(II)/iron­(II) bimetallic cooperative catalytic system proves to be efficient for the formation of various α-alkynyl substituted tetrahydroisoquinolines in good to excellent yields and enantioselectivities. A primary mechanistic study supports an enantioselective electrophilic addition of zinc acetylide to the iminium intermediates, formed through a molecular O2-involved oxidative process.