Generation and Cross-Coupling of Organozinc Reagents in Flow

A versatile flow synthesis method for in situ formation of organozinc reagents and subsequent cross-coupling with aryl halides and activated carboxylic acids is reported. Formation of organozinc reagents is achieved by pumping organic halides, in the presence of ZnCl2 and LiCl, through an activated...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 23; pp. 7429 - 7432
Main Authors Herath, Ananda, Molteni, Valentina, Pan, Shifeng, Loren, Jon
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
ROOM-TEMPERATURE
CATALYSIS
REACTORS
COMPLEXES
DIRECT MAGNESIUM INSERTION
REDOX-ACTIVE ESTERS
FUNCTIONALIZED ARENES
GRIGNARD-REAGENTS
ZINC
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Summary:A versatile flow synthesis method for in situ formation of organozinc reagents and subsequent cross-coupling with aryl halides and activated carboxylic acids is reported. Formation of organozinc reagents is achieved by pumping organic halides, in the presence of ZnCl2 and LiCl, through an activated Mg-packed column under flow conditions. This method provides efficient in situ formation of aryl, primary, secondary, and tertiary alkyl organozinc reagents, which are subsequently telescoped downstream to a Negishi or decarboxylative Negishi cross-coupling reaction. The described method offers access to a variety of C–C bond formations with organozinc reagents that are otherwise commercially unavailable or difficult to prepare under traditional batch reaction conditions.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03156