Amides as modifiable directing groups in electrophilic borylation
Saqib A. Iqbal, Marina Uzelac, Ismat Nawaz, Zhongxing Wang, T. Harri Jones, Kang Yuan, Clément R. P. Millet, Gary S. Nichol, Ghayoor Abbas Chotana, Michael J. Ingleson
Abstract
-octyl-1-BPin-carbazole). Substituent variation is tolerated at boron as well as in the amide unit, with diarylborenium cations also amenable to reduction. This enables a double C-H borylation-reduction-hydrolysis sequence to access B,N-polycyclic aromatic hydrocarbons (PAHs), including an example where both the boron and nitrogen centres contain functionalisable handles (N-H and B-OH). This method is therefore a useful addition to the metal-free borylation toolbox for accessing useful intermediates (ArylBPin) and novel B,N-PAHs.
Topics & Concepts
BorylationChemistryAmideElectrophileMedicinal chemistryAmine gas treatingFuranSubstituentStereochemistryCombinatorial chemistryOrganic chemistryArylAlkylCatalysisOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods