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)

Full Text: HTML

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.

Related Compounds

  • Cupric fluoride
  • Quinidine

Related Articles:

Catalytic enantioselective aldol reaction to ketones.

2006-06-07

[J. Am. Chem. Soc. 128 , 7164, (2006)]

Nucleophilic activation of alkenyl and aryl boronates by a chiral Cu(I)F complex: catalytic enantioselective alkenylation and arylation of aldehydes.

2006-07-17

[Chem. Asian J. 1(1-2) , 161-6, (2006)]

The effect of various fluoride compounds on the development of experimental root surface caries in hamsters.

1995-12-01

[Bull. Tokyo Med. Dent. Univ. 42(3) , 105-16, (1995)]

[Effect of fluoride of copper and iron on polymerization of MMA/TBBO resin and adhesion to dentin].

1989-05-01

[Shika Zairyo. Kikai 8(3) , 425-30, (1989)]

[Study on adhesion mechanism of MMA-TBBO resin to dentin. A model experiment using decalcified dentin].

1990-03-01

[Shika Zairyo. Kikai 9(2) , 320-5, (1990)]

More Articles...