Abstract

In visible light photocatalysis, amines are commonly used as an electron donor to reduce the photoexcited state of organometallic complexes or organic dyes while they are oxidized to amine radical cations. Taking advantage of this facile redox process, we have applied it to ring opening of cyclopropylanilines and cyclobutylanilines. The ring opening process produces distonic radical cations, which are shown to undergo annulation reactions with various types of pi bonds to yield a range of aniline-substituted carbocycles. Several examples of these annulation reactions will be discussed in the talk. Moreover, we have used mass spectrometry coupled with online laser irradiation to investigate the mechanism for one of the annulation reactions, [3+2] annulation of cyclopropylanilines with alkenes. In the talk will also be discussed our findings on the mechanism including the evidence to support the involvement of a chain process.