Literature DB >> 27046019

Catalytic, Diastereoselective 1,2-Difluorination of Alkenes.

Steven M Banik1, Jonathan William Medley1, Eric N Jacobsen1.   

Abstract

We describe a direct, catalytic approach to the 1,2-difluorination of alkenes. The method utilizes a nucleophilic fluoride source and an oxidant in conjunction with an aryl iodide catalyst and is applicable to alkenes with all types of substitution patterns. In general, the vicinal difluoride products are produced with high diastereoselectivities. The observed sense of stereoinduction implicates anchimeric assistance pathways in reactions of alkenes bearing neighboring Lewis basic functionality.

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Year:  2016        PMID： 27046019      PMCID： PMC5097459          DOI： 10.1021/jacs.6b02391

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  23 in total

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  27 in total

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5.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

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8.  Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides.

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9.  Enantioselective Aryl-Iodide-Catalyzed Wagner-Meerwein Rearrangements.

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10.  The Effect of Vicinal Difluorination on the Conformation and Potency of Histone Deacetylase Inhibitors.

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