66543-14-4Relevant academic research and scientific papers
Visible Light Photocatalysis of 6π Heterocyclization
Münster, Niels,Parker, Nicholas A.,van Dijk, Lucy,Paton, Robert S.,Smith, Martin D.
, p. 9468 - 9472 (2017)
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 IrIII 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.
