Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation

Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation
Takeshi Ohkuma, Noriyoshi Arai
Aza-Diels–Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to-catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20–25 °C), affording the cycloaddition product in 97% yield.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00838

DOI: 10.1021/acs.joc.7b00838

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