Selective Fluoroalkylations with Fluorinated Sulfones, Sulfoxides, and Sulfides^†

G. K. Surya Prakash was born in Bangalore, India, in 1953. He received a B.Sc. (Honors) degree in 1972 from the Bangalore University and a M.Sc. Degree from Indian Institute of Technology, Madras, in 1974. He obtained his Ph.D. degree from the University of Southern California (USC) in 1978 under the tutelage of George A. Olah. After his postdoctoral work at USC, he joined the faculty in the Loker Hydrocarbon Research Institute and thereafter the Department of Chemistry at USC. Currently, he is a full professor in chemistry and Scientific Co-director of the Loker Hydrocarbon Research Institute at USC. He also holds the George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry with research contributions and interests in selective fluorination methods, new synthetic methods, mechanistic studies of organic reactions, electrochemistry, and superacid and hydrocarbon chemistry. He has received many honors and accolades including the 2004 ACS Award for Creative Work in Fluorine Chemistry, the 2006 George A. Olah Award in Hydrocarbon or Petroleum Chemistry, and the 2006 Tolman Award.

Jinbo Hu was born in Zhejiang, China (1973). He completed his B.S. (1994) and M.S. degrees (1997) at Hangzhou University and Chinese Academy of Sciences (CAS), respectively. He did his Ph.D. work during 1997−2002 at the University of Southern California (USC) with Professors G. K. S. Prakash and G. A. Olah. After his postdoctoral work at USC with Professors Prakash and Olah, he accepted the Research Professorship at Shanghai Institute of Organic Chemistry (SIOC), CAS in early 2005. The same year he received the Faculty Excellence Award by Air Products Inc. His main research interests are in selective fluorination methodologies and fluorinated materials.

Efficient fluoroalkylations have been proven to be a highly useful strategy for the synthesis of bioactive fluorine-containing compounds and other materials. The design and use of a single category of reagents for multiple synthetic goals are much more attractive to preparative organic chemists. In this Account, we show how we have succeeded in the nucleophilic trifluoromethylation, difluoromethylation, difluoromethylenation, (phenylsulfonyl)difluoromethylation, (phenylthio)difluoromethylation, and monofluoromethylation as well as radical (phenylsulfonyl)difluoromethylation and electrophilic difluoromethylation by using fluorinated sulfones, sulfoxides, sulfides, or fluorinated sulfonium salts. The chemistry not only provides practically powerful synthetic methods, but the molecular design concept that we have developed may also be adopted to tackle other related chemical problems.