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Synfacts 2013; 9(6): 0649
DOI: 10.1055/s-0033-1338732
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Direct Difluoroethylation of Hetero-aromatics, Michael Acceptors and Thiols

Rezensent(en):
Paul Knochel
,
Andreas K. Steib
Zhou Q, Ruffoni A, Gianatassio R, Fujiwara Y, Sella E, Shabat D, Baran PS * The Scripps Research Institute, La Jolla, USA and Tel-Aviv University, Israel
Direct Synthesis of Fluorinated Heteroarylether Bioisosteres.

Angew. Chem. Int. Ed. 2013;
52: 3949-3952
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Publikationsverlauf

Publikationsdatum:
16. Mai 2013 (online)

 
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Key words

difluoroethylation - bioisosteres - C–H functionalization

Significance

A novel protocol for direct difluoroethylation of a broad range of heterocycles, ­Michael acceptors and even thiols with sodium difluoroethylsulfinate (DFES-Na) has been described. DFES-Na is shown to be compatible with various sensitive functional groups, reacts site selectively in high conversion and is easy to handle.


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Comment

Interestingly, performing the reaction with DFES-Na and tert-butylhydroperoxide (TBHP) solely results in only traces of the desired product. Only after addition of stoichiometric amounts of ZnCl2 and TsOH·H2O, the product is obtained in high yield.


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