Silver‐Catalyzed Intramolecular Aminofluorination of Activated Allenes

Abstract

A nice combination: the intramolecular oxidative aminofluorination of allenes using silver catalysis and FN(SO(2)Ph)(2) as the fluorinating reagent has been developed. This reaction represents an efficient method for the synthesis of various 4-fluoro-2,5-dihydropyrrole compounds. Further transformation provided the corresponding fluorinated pyrrole derivatives in good yields.

Metal Carbides as Alternative Electrocatalyst Supports

“…8,9 The endo-cyclization of 2-substituted 2-allenyl sulfonamamides catalyzed by AgNO 3 in the presence of N -fluorobenzenesulfonimide (NFSI, 1.5 equiv) produced a range of 3-fluoro-3,4-unsaturated pyrrolidines in moderate to excellent yield (Scheme 5). 8 It should also be noted that Pd-catalyzed exo-cyclization/aminohalogenation of allenes have previously been reported by Backvall and co-workers. 10 …”

Chromium(II)-catalyzed enantioselective arylation of ketones

“…Phenyl ketone 1d and ketones with electron-withdrawing groups in different substituent patterns gave the expected products with good enantiocontrol, while the enantioselectivity for ketone 1e bearing an electron-donating group decreased. The mild process exhibited excellent functional group tolerance, with chloride ( 2f ), fluoride ( 2g ), and CF 3 moieties ( 2h ) well tolerated for further manipulation [46–47]. Heteroaryl ketones such as furan-substituted ketone ( 1i ) were also suitable substrate, giving product 2i in 78% ee.…”

Catalytic Aminohalogenation of Alkenes and Alkynes

“…8). 59 (8) The first enantioselective intramolecular aminofluorination was reported by Gouverneur and co-workers in 2011. 60 Various tryptamine derivatives underwent electrophilic fluorination/ cyclization using N-fluorobenzenesulfonamide (NFSI) in the presence of 20 mol% of Sharpless's (DHQ) 2 PHAL ligand (Scheme 36).…”