The stereospecific Barbier reaction between (Z)- and (E)-1-iodopentafluoropropenes, zinc and aldehydes

Fluorinated stannanes

“…As part of a mechanistic study of the Barbier reaction, the methodology was extended to the synthesis of fluorinated stannanes [5]. (Z)-1-iodo-1,2,3,3,3-pentafluoropropene reacted efficiently with tri-n-butyltin chloride in the presence of zinc to stereospecifically yield the corresponding stannane in good yields (Scheme 1).…”

“…In an earlier report from this group, a novel Barbiertype reaction of fluorinated vinyl and aryl iodides with aldehydes in the presence of zinc to stereospecifically yield partially fluorinated alcohols was discussed [5]. Mechanistic details as well as scope of the reaction were also elucidated [5].…”

Trifluoromethylated Vinylic and Aromatic Compounds from α-(Trifluoro­methyl)allyl Alcohols

“…[17][18][19][20][21] The third route is based on b-metalation of a,a,a-trifluoropropenes, followed by condensation with an aldehyde. [22][23][24][25][26] This method has been also used to prepare b-(trifluoromethyl)allyl alcohols from 2-bromo-1,1,1-trifluoropropene. 30 The g-(trifluoromethyl)allyl alcohols produced have been used in several fruitful transformations such as hydroxyl/halogen exchange followed by S N 2 substitution 12,14 or indium-mediated condensation on carbonyl compounds.…”

Fluorinated Organozinc Reagents

“…Jairaj and Burton have studied the mechanistic details of the reaction between Z-1-iodopentafluoropropene with Zn • and have presented mechanistic evidence consistent with the formation of a vinyl carbanion that is captured in situ by zinc halide to form the vinylzinc reagent 45 . Their mechanism is presented in Scheme 1.…”