title: Enantioselective Suzuki cross-couplings of unactivated 1-fluoro-1-haloalkanes: synthesis of chiral β-, γ-, δ-, and ε-fluoroalkanes.
abstract: The incorporation of fluorine atom into a stereogenic center is a highly challenging transformation with current methodologies offering access mainly to chiral α- and β-fluoroalkanes. In this article, the development of a novel general approach to construct β-, γ-, δ-, and ε- fluoroalkanes with good enantioselectivity is described. Different directing groups, such as benzyl, ketone, and sulfonyl, were shown to give good enantioselectivity under Suzuki cross-coupling conditions in the presence of a Ni catalyst and chiral diamine ligand. It includes the first examples of enantioselective synthesis of chiral fluorine-containing centers at as distant as δ or ε positions from the functional groups.
authors: Schulich Faculty of Chemistry, Technion-Israel Institute of Technology , Technion City, Haifa 32000, Israel.
authors: Xiaojian
authors: X
authors: Jiang
authors: Mark
authors: M
authors: Gandelman
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D006845:Hydrocarbons, Fluorinated