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J Am Chem Soc. 2015 Feb 25;137(7):2542-7. doi: 10.1021/jacs.5b00473. Epub 2015 Feb 16.

Enantioselective Suzuki cross-couplings of unactivated 1-fluoro-1-haloalkanes: synthesis of chiral β-, γ-, δ-, and ε-fluoroalkanes.

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Schulich Faculty of Chemistry, Technion-Israel Institute of Technology , Technion City, Haifa 32000, Israel.


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.

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