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

Xiaojian Jiang, Mark Gandelman

Research output: Contribution to journalArticlepeer-review

67 Scopus citations

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.

Original languageEnglish
Pages (from-to)2542-2547
Number of pages6
JournalJournal of the American Chemical Society
Volume137
Issue number7
DOIs
StatePublished - 25 Feb 2015
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

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