In this talk, I will present a selection of new synthetic strategies for assembling poly- and heteroaromatic systems.
In the 1st part, I will discuss the advantages of alkynes as high-energy carbon-rich precursors for extended polyaromatics, the two general patterns of oligoalkyne folding into an aromatic ribbon, and the use of supramolecular effects in the design of traceless directing groups for radical reactions.
In the 2nd part, I will present a mild method for oxidative C(sp3)–H amination from unprotected anilines and C(sp3)–H bonds. In this process, basic, radical, and oxidizing species work together in a coordinated sequence of deprotonation, H-atom transfer and electron transfer that forges a new C–N bond. I will also introduce reductant upconversion, a new concept in catalysis, and show how it can be used for preventing the premature entry of oxidants into reaction cascades.
References: Acc. Chem. Res., 2018, 51, 1206-1219. Angew. Chem. Int. Ed., 2018, 57, https://doi.org/10.1002/anie.201807247.