Visible Light Photocatalysis of 6π Heterocyclization.

ABSTRACT: Photo-mediated 6π cyclization is a valuable method for the formation of fused heterocyclic systems. Here we demonstrate that irradiation of cyclic 2-aryloxyketones with blue LED light in the presence of an Ir^III complex leads to efficient and high yielding arylation across a panoply of substrates by energy transfer. 2-Arylthioketones and 2-arylaminoketones also cyclize effectively under these conditions. Quantum calculation demonstrates that the reaction proceeds via conrotatory ring closure in the triplet excited state. Subsequent suprafacial 1,4-hydrogen shift and epimerization leads to the observed cis-fused products.

SUBMITTER: Munster N 

PROVIDER: S-EPMC5575533 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature