Work

Fluoro-Julia Olefination as a Mild, High-Yielding Route to α-Fluoro Acrylonitriles

Year: 2008

Type: article

Abstract: 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo801235x

Authors: Maria del Solar, Arun K. Ghosh, Barbara Zajc

Institutions: City College of New York, City University of New York

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Science Foundation, National Institute of General Medical Sciences, National Center for Research Resources

Awards: Cellular/Molecular Basis of Development: Research Center, Research Support for Biomedical Careers at CCNY