LiCl-Mediated Preparation of Highly Functionalized Benzylic Zinc Chlorides

LiCl-Mediated Preparation of Highly Functionalized Benzylic Zinc Chlorides

In the presence of zinc dust (1.5−2.0 equiv) and LiCl (1.5−2.0 equiv), various benzylic chlorides bearing functional groups (iodide, cyanide, ester, ketone) are smoothly converted at 25 °C to the corresponding zinc reagents without homo-coupling (<5%). The utility of these benzylic zinc reagents...

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Bibliographic Details
Published in:Organic letters Vol. 10; no. 6; pp. 1107 - 1110
Main Authors: Metzger, Albrecht, Schade, Matthias A, Knochel, Paul
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-03-2008
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Summary:In the presence of zinc dust (1.5−2.0 equiv) and LiCl (1.5−2.0 equiv), various benzylic chlorides bearing functional groups (iodide, cyanide, ester, ketone) are smoothly converted at 25 °C to the corresponding zinc reagents without homo-coupling (<5%). The utility of these benzylic zinc reagents is demonstrated by a short synthesis of papaverine.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol7030697