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Palladium-Catalyzed Chemoselective Negishi Cross-Coupling of Bis[(pinacolato)boryl]methylzinc Halides with Aryl (Pseudo)Halides

Title
Palladium-Catalyzed Chemoselective Negishi Cross-Coupling of Bis[(pinacolato)boryl]methylzinc Halides with Aryl (Pseudo)Halides
Authors
CHO, SEUNG HWANLEE, HYOJAELEE, YEOSAN
Date Issued
2-Aug-2019
Publisher
AMER CHEMICAL SOC
Abstract
We describe a palladium-catalyzed chemo-pharmaceutical selective Negishi cross-coupling of a bis[(pinacolato)boryl]-methylzinc halide with aryl (pseudo)halides. This reaction affords an array of benzylic 1,1-diboronate esters, which can serve as useful synthetic handles for further transformations. The developed coupling reaction is compatible with various functional groups and can be easily scaled up. The coupling of bis[(pinacolato)boryl]methylzinc halides with pharmaceuticals and the subsequent late-stage manipulations demonstrate the power of the developed protocol.
Keywords
ASYMMETRIC-SYNTHESIS; BORON REAGENTS; ESTERS; DIBORYLATION; BORYLATION; ALLYLATION; ALDEHYDES; FUNCTIONALIZATION; HYDROBORATION; OLIGOARENES
URI
http://oasis.postech.ac.kr/handle/2014.oak/99575
ISSN
1523-7060
Article Type
Article
Citation
ORGANIC LETTERS, vol. 21, no. 15, page. 5912 - 5916, 2019-08-02
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 CHO, SEUNG HWAN
Dept of Chemistry
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