Photochemical Gold Catalyzed Domino Reaction for the Synthesis of Indolines and Tetrahydroquinolines

Key words

gold catalysis - photochemical - domino process - radical addition - indolines - tetrahydroquinolines

Significance

The authors report the synthesis of indolines and tetrahydroquinolines through the coupling of an N-aryl-N-allylamine and a bromoalkane in a gold-catalyzed photochemical domino reaction. Using this method, they were able to synthesis a biologically active compound precursor. The reaction is amenable to a variety of electron donating and withdrawing groups on the aromatic ring.

Comment

The authors show that the inclusion of Na-ascorbate increases the yield from 40% to 81%. This additive has been shown to increase the effectiveness of the gold photocatalyst used. They hypothesize that after radical addition to the allyl amine the intermediate can either cyclize in a radical process and then be oxidized or can be oxidized and then cyclize through an EAS reaction.

Publication History

Article published online:
25 July 2024