Diethylaminosulfur trifluoride (DAST) is ideal for nucleophilic fluorination and has been used in selective fluorinations of alcohols, alkenols, carbohydrates, ketones, sulfides, epoxides, thioethers, and cyanohydrins.
The functional-group-tolerant, one-step conversion of phenols to aryl fluorides is a highly desirable process. PhenoFluor™ solution, provides straightforward method to fluorinate alcohol and phenols without preactivation and regioselectively fluorinate highly functionalized late-stage intermediates.
The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as stoichiometric chiral reagents or in Lewis acid mediated reactions, to roles in catalytic hydrogenation and stereoregular metathesis polymerization.
Fluoroamidinium salts were an advance in acid halogenation. Compared to chlorides, acid fluorides have greater water stability and a lack of conversion to the corresponding oxazolones upon treatment with organic bases.
The fluoroalkylation toolbox now includes Togni reagents, hypervalent iodine perfluoroalkylation reagents, fluoroalkyl bromides, silanes, carboxylates, and sulfonyl fluorides for late stage fluoroalkylation.
Selectfluor™ (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), or F-TEDA) is a user-friendly, mild, air- and moisture-stable, non-volatile reagent for electrophilic fluorination.
A solid and bench-stable alternative to sulfuryl fluoride gas has been developed, 4-(Acetylamino)phenyl]imidodisulfuryl difluoride (ASIF). ASIF is a shelf-stable, crystallilne reagent for the installation of the valuable SO2F functional group.