Visible-light-induced cyanation of aza-Baylis-Hillman adducts: a Michael type addition

Visible-light-induced aerobic oxidative cyanation of aza-Baylis-Hillman (aza-BH) adducts providing valuable allylic cyanides in good to excellent yields has been developed. The protocol involves in situ formation of 4 pi conjugated iminium ion intermediates, which undergo cyanation at the gamma-position to afford Michael type adducts. This is the first example of visible-light-induced catalytic functionalization of aza-BH adducts using air (O-2) as an economical and ecosustainable oxidant and TMSCN as a convenient and readily available cyanide source. (C) 2014 Elsevier Ltd. All rights reserved.