Geri, Jacob B.; Wade Wolfe, Michael M.; Szymczak, Nathaniel K. published the artcile< The Difluoromethyl Group as a Masked Nucleophile: A Lewis Acid/Base Approach>, Recommanded Product: (9Z,12Z)-Methyl octadeca-9,12-dienoate, the main research area is difluoromethyl arene heteroarene preparation difluoromethyl group masked nucleophile electrophile; Lewis acid bronsted superbase deprotonation aryl difluoromethyl synthon intermediate.
The difluoromethyl group (R-CF2H) imparts desirable pharmacokinetic properties to drug mols. and is commonly targeted as a terminal functional group that is not amenable to further modification. Deprotonation of widely available Ar-CF2H starting materials to expose nucleophilic Ar-CF2- synthons represents an unexplored, yet promising route to construct benzylic Ar-CF2-R linkages. Here we show that the combination of a Bronsted superbase with a weak Lewis acid enables deprotonation of Ar-CF2H groups and capture of reactive Ar-CF2- fragments. This route provides access to isolable and reactive Ar-CF2- synthons that react with a broad array of electrophiles at room temperature The methodol. is highly general in both electrophile and difluoromethyl (hetero)arene and can be applied directly to the synthesis of benzylic difluoromethylene (Ar-CF2-R) linkages, which are useful lipophilic and metabolically resistant replacements for benzylic linkages in medicinal chem.
Journal of the American Chemical Society published new progress about Bronsted bases Role: RGT (Reagent), RACT (Reactant or Reagent). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Recommanded Product: (9Z,12Z)-Methyl octadeca-9,12-dienoate.
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