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Palladium-catalyzed allylic fluorination of cinnamyl phosphorothioate esters.

Organic letters (2012-09-25)
Andrew M Lauer, Jimmy Wu
ABSTRACT

A highly regioselective, Pd-catalyzed allylic fluorination of phosphorothioate esters is reported. This chemistry addresses several limitations of previously reported methods in which elimination and lack of reactivity were problematic. Preliminary mechanistic investigations reveal that these reactions are stereospecific and provide fluorinated products with net retention of stereochemical configuration. In analogy to other Pd-catalyzed allylic substitution reactions, this process likely proceeds through a palladium π-allyl intermediate.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
trans-Cinnamic acid, natural, ≥99%, FCC, FG
Sigma-Aldrich
trans-Cinnamic acid, ≥99%, FG
Supelco
trans-Cinnamic acid, analytical standard
Sigma-Aldrich
trans-Cinnamic acid, 97%
Sigma-Aldrich
trans-Cinnamic acid, ≥99%