4 years ago

Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes

Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes
Tianyu Huang, Jiawen Lang, Lili Lin, Xiaohua Liu, Jian Xu, 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.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b01912

DOI: 10.1021/acscatal.7b01912

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