Synthesis of mono-fluorinated functionalized cyclopropanes and aziridines using the α-fluorovinyl diphenyl sulfonium salt.

The α-fluorovinyl diphenyl sulfonium salt 1 is attractive due to its high potential for the synthesis of mono-fluorinated cyclopropanes and aziridines as useful three-membered rings. The synthetically useful salt 1 is readily prepared from α-fluorovinyl phenyl sulfide and diphenyl iodonium salt in one step.

Synthesis of 2-aryl-3-fluoro-5-silylthiophenes via a cascade reactive sequence.

2-Aryl-3-fluoro-5-silylthiophenes were readily prepared only in two steps from 2-bromo-3,3,3-trifluoropropene in good yields. These transformations include the first successful S(N)2'-type reaction of 2-bromo-3,3,3-trifluoropropene and benzylthiols and [2,3]sigmatropic rearrangement of 2-bromo-3,3-difluoroallyl benzyl sulfide.

AgSbF6-promoted cycloaddition reaction of 2-trifluoromethyl-N-tosylaziridine with aldehydes.

2-Trifluoromethyl-N-tosylaziridine reacted with various aldehydes in the presence of a catalytic amount of AgSbF(6) to provide the corresponding cis-4-trifluoromethyl-2-substituted-N-tosyl-1,3-oxazolidines with excellent regio- and stereoselectivity.

Mizoroki-Heck reaction of (1-fluorovinyl)methyldiphenylsilane with aryl iodides.

The Mizoroki-Heck reaction of (1-fluorovinyl)methyldiphenylsilane with a variety of aryl iodides was accomplished under the conditions composing Pd(OAc)(2), Ag(2)CO(3) and MS 4 Å in 1,4-dioxane to give the corresponding (E)-β-aryl-(α-fluorovinyl)methyldiphenylsilanes with excellent stereoselectivity.