Oxidative Para-triflation of Acetanilides
Overview
Chemistry
Affiliations
Direct triflation of acetanilide derivatives with silver triflate has been accomplished under mild iodine(III)-mediated oxidative conditions. The reaction shows excellent regioselectivity for the para position and tolerates a range of ortho and meta substituents on the aromatic ring. This method is also compatible with the preparation of arylnonaflates in synthetically useful yields.
SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates.
Li B, Voets L, Van Lommel R, Hoppenbrouwers F, Alonso M, Verhelst S Chem Sci. 2022; 13(8):2270-2279.
PMID: 35310484 PMC: 8864708. DOI: 10.1039/d1sc06267k.
Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide.
McErlain H, Riley L, Sutherland A J Org Chem. 2021; 86(23):17036-17049.
PMID: 34726917 PMC: 8650017. DOI: 10.1021/acs.joc.1c02172.
Cu(OTf)-catalyzed Beckmann Rearrangement of Ketones Using Hydroxylaminesulfonic Acid (HOSA).
Munnuri S, Verma S, Chandra D, Anugu R, Falck J, Jat J Synthesis (Stuttg). 2020; 51(19):3709-3714.
PMID: 32684655 PMC: 7367085. DOI: 10.1055/s-0039-1690005.
Site-Selective C-H Functionalization of (Hetero)Arenes via Transient, Non-Symmetric Iodanes.
Fosu S, Hambira C, Chen A, Fuchs J, Nagib D Chem. 2019; 5(2):417-428.
PMID: 31032461 PMC: 6481961. DOI: 10.1016/j.chempr.2018.11.007.