Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

Among cross-coupling reactions, the Suzuki–Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to...

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Bibliographic Details
Published in:Organic letters 2016-09, Vol.18 (17), p.4440-4443
Main Authors: Laulhé, Sébastien, Blackburn, J. Miles, Roizen, Jennifer L
Format: Article
Language:English
Subjects:
aromatic compounds
boronic acids
cross-coupling reactions
esters
Letter
moieties
organic halogen compounds
toxicity
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Summary:Among cross-coupling reactions, the Suzuki–Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki–Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b02323