Organic & Biomolecular Chemistry 2012-12-21

Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt.

Shaoxiang Wu, Wei Zeng, Qi Wang, Fu-Xue Chen

Index: Org. Biomol. Chem. 10(47) , 9334-7, (2012)

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Abstract

A general enantioselective trifluoromethylation of aldehydes has been developed using (IPr)CuF and quinidine-derived quaternary ammonium salt as the cooperative catalyst. Thus, a wide range of aromatic aldehydes have been converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. The greatly enhanced activity and enantioselectivity result from the initiative generation of active [(IPr)CuCF(3)] as well as additional coordination activation of other copper species.