Trimethylsulfonium Fluoride andn-Butyldimethylsulfonium Fluoride: New Methylating Agents for Nucleosides and Related Compounds

Alkylation Reactions with Alkylsulfonium Salts

“…synthesized in good to excellent yield by heating 9 and benzyl halides in the presence or absence of solvent. 15 Závada and coworkers reported that reactions of 4-alkyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]thiepin-4-ium (13) with a range of N-, S-, Se-, O-, and C-nucleophiles afforded the corresponding ring opening bidentate products (14) and/or dealkylative product (12), which was dependent upon the counteranions of the sulfoniums (Scheme 3c). 16 In most instances, iodide caused the formation of 12, while perchlorate, tetraphenyl borate, and tetrafluoroborate favored the production of 14.…”

“…Treatment of guanosine ( 1 ) with [Me 3 S]F formed 1-methylguanosine ( 2a ) in 67% yield, while the similar reaction with [Me 3 S]I provided 7-methylguanosine ( 2b) in 54% yield (Scheme 1 ). 12 The difference in the selectivity of methylation might be attributed to the hydrogen bonding between the fluoride anion and amide/imide groups in the substrates, which increased the nucleophilicity of the groups and enhanced the attack of sulfonium cations.…”

Oligomeric Benzylsulfonium Salts: Facile Benzylation via High-Load ROMP Reagents

“…Prominent among the uses of such salts are their conversion into sulfonium ylides for use in the Corey epoxidation procedure and for alkylation of nucleophiles. Examples of the latter include reactions with azide ion, carboxylates, nucleosides, phenols and thiophenols, amines, cyanides, amides, enolates, and sulfenates . Application in Pd-catalyzed carbon−carbon formations has also been reported …”