One-pot, Two-step, Microwave-assisted Palladium-catalyzed Conversion of Aryl Alcohols to Aryl Fluorides Via Aryl Nonaflates
Overview
Affiliations
A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.
Marshall O, McGrory R, Songsri S, Thomson A, Sutherland A Chem Sci. 2025; 16(8):3490-3497.
PMID: 39886437 PMC: 11775655. DOI: 10.1039/d5sc00020c.
Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids.
Ruffell K, Argent S, Ling K, Ball L Angew Chem Int Ed Engl. 2022; 61(40):e202210840.
PMID: 35950691 DOI: 10.1002/anie.202210840.
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.
Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.
Li X, Shi X, Li X, Shi D Beilstein J Org Chem. 2019; 15:2213-2270.
PMID: 31598178 PMC: 6774084. DOI: 10.3762/bjoc.15.218.
In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides.
Milner P, Yang Y, Buchwald S Organometallics. 2016; 34(19):4775-4780.
PMID: 27056379 PMC: 4820280. DOI: 10.1021/acs.organomet.5b00631.