Total synthesis of 7,7-, 10,10-, and 13,13-difluoroarachidonic acids

Sulfoximines as a Versatile Scaffold for Electrophilic Fluoroalkylating Reagents

“…[22] During the initiation step, the nucleophilic species generates a difluoromethyl (or chlorofluoro) carbene which is then able to start a catalytic cycle for the production of the fluoro-alkylated material (Scheme 4). The significant amount of molecules 11a and 11b indicates that the initiation reaction competes efficiently with the catalytic cycle.…”

Selective Green Coupling of Alkynyltins and Allylic Halides to Trienynes via a Tandem Double Stille Reaction

“…The reactants Bu 3 SnCl, Bu 3 SnH, phenylethynyltributyltin, dodeca-5,7-diyne, the organic halides and the terminal alkynes were obtained from commercial suppliers and used without further purification. The compounds Copol-NB-NB-Sn(Bu) 2 Cl, [3] cuprous butylacetylide, [13] A…”

Fluorinated Organozinc Reagents

“…These workers utilized this reaction to prepare α-difluorovinyl substituted β-hydroxyesters in high yields and high regioselectivity via the reactions of aldehydes mediated by zinc (equation 89) 82 . Fried and coworkers prepared fluorine-containing propargylic halides via reaction of alkynyllithium reagents with CF 2 BrCl (equation 91) 83 . These workers utilized these propargylic halides for the total synthesis of 7,7-10,10-and 13,13-difluoroarachidonic acids.…”