Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles.
Synthesis of a novel, stable reagent (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile from readily synthesized ethyl alpha-(1,3-benzothiazol-2-ylsulfanyl)-alpha-fluoroacetate is reported. Aldehydes undergo condensations with (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile in the presence of DBU leading to alpha-fluoro acrylonitriles in high yields and with good Z-stereoselectivity. Lowering of reaction temperature increases the Z selectivity.
Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, New York 10031-9198, USA.
Maria
M
del Solar
Arun K
AK
Ghosh
Barbara
B
Zajc
D000181:Acrylonitrile / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D005461:Fluorine; D000181:Acrylonitrile