Photoredox Catalytic Three-Component Amidoazidation of 1,3-Dienes
Dan Forster, Weisi Guo, Qian Wang, Jieping Zhu
Abstract
In spite of the obvious synthetic potential of functionalized allylic azides, only limited synthetic routes have been developed. We report herein a three-component 1,2-amidoazidation of 1,3-dienes. In the presence of fac-Ir(ppy)3 under blue LED irradiation, reaction of 1-aryl substituted 1,3-dienes with N-amidopyridinium salt and trimethylsilyl azide (TMSN3) affords exclusively the 1,2-amidoazidation products. The 1-alkyl substituted counterparts undergo the same reaction with moderate to high 1,2- vs 1,4-selectivity. Reduction of this mixture with PPh3 under dynamic kinetic conditions enriches significantly one of the two isomers thanks to the facile 1,3-azide shift (Winstein rearrangement) of the allyl azides.