Organic Chemistry Portal



N-Heterocyclic Carbene Catalyzed Highly Chemoselective Intermolecular Crossed Acyloin Condensation of Aromatic Aldehydes with Trifluoroacetaldehyde Ethyl Hemiacetal

Bandaru T. Ramanjaneyulu, Sriram Mahesh and Ramasamy Vijaya Anand*

*Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Sector 81, Knowledge City, S. A. S. Nagar, Manauli (PO), Punjab - 140306, India, Email:

B. T. Ramanjaneyulu, S. Mahesh, R. V. Anand, Org. Lett., 2015, 17, 6-9.

DOI: 10.1021/ol502581b


A N-heterocyclic carbene as a catalyst enables a highly chemoselective intermolecular crossed acyloin condensation between aromatic aldehydes and trifluoroacetaldehyde ethyl hemiacetal under mild reaction conditions. A wide range of aromatic aldehydes underwent a smooth transformation to trifluoromethylated acyloin derivatives in good yields.

see article for more examples

Key Words

acyloin condensation, trifluoromethyl carbinols, α-trifluoromethyl carbonyl compounds, organocatalysis

ID: J54-Y2015