Synlett 2012; 23(5): 807-808
DOI: 10.1055/s-0031-1290294
© Georg Thieme Verlag Stuttgart · New York


Amanda Silva de Miranda
LASSBio, sala B16, CCS, Universidade Federal do Rio de Janeiro, CEP 21944-470, Rio de Janeiro, Brazil, Email:
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Publication History

Publication Date:
28 February 2012 (online)


Fluorination is a very useful strategy in the design and synthesis of bioactive compounds, since the special nature of fluorine can confer enhanced binding interactions, metabolic stability and desirable physical properties to a molecule. In fact, approximately 5–15% of the total number of drugs launched in the past 50 years were fluorinated compounds and this percentage has noticeably increased in the past five years.[ 1 ] Recently, a novel deoxofluorinating agent, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (named Fluolead™, 1) has been reported.[2] [3] Fluolead™ is a versatile reagent with relative high thermal and hydrolytic stability that fluorinates a broad range of substrates, generally more efficiently and selectively than currently available deoxofluorinating agents, such as diethylaminosulfur trifluoride (DAST), Deoxo-Fluor™ and other related reagents.[ 2,3,6,14 ] In addition, it can be obtained from commercial sources or be easily prepared in two steps from commercial available 5-tert-butyl-m-xylene (Scheme [1]).[2] [5] Because it is versatile, efficient, shelf-stable, easy-to-handle, and relative highly safe, Fluo­lead™ is expected to be widely used in both academic and industrial areas.[ 2 ]

Zoom Image
Scheme 1
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