Synthesis 2010(11): 1899-1904  
DOI: 10.1055/s-0029-1218752
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Magnesium Metal-Mediated Reductive Trifluoromethylation of Aldehydes with Phenyl Trifluoromethyl Sulfone

Yanchuan Zhao, Jieming Zhu, Chuanfa Ni, Jinbo Hu*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, P. R. of China
e-Mail: jinbohu@sioc.ac.cn;
Further Information

Publication History

Received 28 February 2010
Publication Date:
23 April 2010 (eFirst)

Abstract

An unprecedented reductive nucleophilic trifluoromethylation of aldehydes by using phenyl trifluoromethyl sulfone is reported. Mercury(II) chloride efficiently activates magnesium metal to induce the desulfonylative trifluoromethylation process. The new reductive trifluoromethylation provides an alternative method for efficient trifluoromethylation of non-enolizable or enolizable aldehydes with readily available phenyl trifluoromethyl sulfone reagent.