Efficient nucleophilic fluoromethylation and subsequent transformation of alkyl and benzyl halides using fluorobis(phenylsulfonyl)methane.
An efficient methodology for the nucleophilic fluoromethylation of alkyl and benzyl halides using alpha-fluoro-alpha-(phenylsulfonyl)methane (1) as a highly versatile reagent is reported. Using benzyl halides, stereospecific one-pot synthesis of alpha-fluorovinyl compounds such as alpha-fluorostyrylsulfones, alpha-fluorocinnamates, and alpha-fluorochalcones has been achieved. The methodology has been extended toward the synthesis of alpha-substituted fluoroalkane derivatives using selective reductive desulfonylation conditions.
Prakash
G K Surya
GK
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA. gprakash@usc.edu
Chacko
Sujith
S
Vaghoo
Habiba
H
Shao
Nan
N
Gurung
Laxman
L
Mathew
Thomas
T
Olah
George A
GA