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Merck

Trifluoromethylation of allylsilanes under photoredox catalysis.

Organic letters (2013-03-08)
Satoshi Mizuta, Keary M Engle, Stefan Verhoog, Oscar Galicia-López, Miriam O'Duill, Maurice Médebielle, Katherine Wheelhouse, Gerasimos Rassias, Amber L Thompson, Véronique Gouverneur
ABSTRACT

A new catalytic method to access allylic secondary CF3 products is described. These reactions use the visible light excited Ru(bpy)3Cl2·6H2O catalyst and the Togni or Umemoto reagent as the CF3 source. The photoredox catalytic manifold delivers enantioenriched allylic trifluoromethylated products not accessible under Cu(I) catalysis.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Copper(I) chloride, ≥99.995% trace metals basis
Sigma-Aldrich
Copper(I) chloride, AnhydroBeads, ≥99.99% trace metals basis
Sigma-Aldrich
Copper(I) chloride, ReagentPlus®, purified, ≥99%
Sigma-Aldrich
Copper(I) chloride, reagent grade, 97%