Organofluorine chemistry1 has been of great interest recently due to its wide range of applications. Currently, around twenty percent of all pharmaceuticals contain at least one fluorine atom. The trifluoromethyl group is particularly important in drug discovery due to its strong electron-withdrawing character, high hydrophobicity, increased bioavailability, and metabolic stability. However, many current techniques for introducing the trifluoromethyl group to compounds employ harsh conditions that are not environmentally friendly. In this research, nucleophilic trifluoromethylation of various electrophiles including aldehydes, ketones, and imines has been accomplished using a calcium catalyst under mild conditions.  Additionally, the scope of aldehydes amenable to this method has proven to be broad including aliphatic and heteroaromatic aldehydes as well as aldehydes containing electron withdrawing (nitrile and trifluoromethyl) groups and electron donating (methoxy and hydroxyl) groups. Mizuta, S. et al. Tetrahedron Asymmetry, 2008, 19, 2633.

Calcium-catalyzed nucleophilic trifluoromethylation

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.