2-Fluorovinyl tosylate

Cross-Coupling Reaction Using 2-Fluorovinyl Tosylate. 71... 

Fluorovinyl tosylate 40 was stereoselectively prepared from commercially available 2,2,2-trifluoroethyl tosylate in two steps. A pure ( )-40, isolated by column chromatography, was used in the Suzuki-Miyaura coupling with (4-methoxyphenyl)boronic acid, and ( )-(2-fluorovinyl)-4-methoxybenzene 41 was obtained stereoselectively [66] (Scheme 14). 

Scheme 14 Cross-coupling reaction using 2-fluorovinyl tosylate 40...

Cycloaddition Reactions. The reaction of pyridinium, iso-quinolinium, and benzimidazolinium 7V-ylide with fluorovinyl tosylate 1 gives cyclic monofluorinated adducts in moderate yield (eq 6). The reaction mechanism is thought to involve initial 1,3-dipolar cycloadditon of the TV-ylide to 1, followed by elimination of both tosic and hydrofluoric acid. ... 

Anion Chemistry. The fluorovinyl anion 3 (eq 1) is a versatile intermediate and can be reacted with a variety of electrophiles. When treated with ketones, the anion gives secondary alcohols which can be sequentially hydrolyzed, firstly to carboxy enol-tosylates under acidic conditions, and then under basic conditions to give synthetically useful a-keto carboxylic acids (eq 2). ... 

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See also in sourсe #XX -- [ ]

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