High-yield synthesis of fluorinated benzothiazolyl sulfones: general synthons for fluoro-julia olefinations.
[reaction: see text] General, high-yield tandem electrophilic fluorination and modified Julia olefination for the synthesis of fluoro olefins is reported. A series of alpha-fluoro 1,3-benzothiazol-2-yl sulfone-based synthons were synthesized via deprotonation-fluorination. Of critical importance for high-yield fluorinations were heterogeneous reaction conditions, as under homogeneous conditions only starting sulfones were recovered. The alpha-fluoro 1,3-benzothiazol-2-yl sulfones so obtained were subjected to condensations with a variety of aldehydes and ketones to afford high yields of regiospecifically fluorinated olefins.
Ghosh
Arun K
AK
Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, New York 10031, USA.
Zajc
Barbara
B
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D052160:Benzothiazoles; D006845:Hydrocarbons, Fluorinated; D013450:Sulfones