Journal
ORGANIC LETTERS
Volume 21, Issue 15, Pages 5912-5916Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02050
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Funding
- National Research Foundation of Korea - Korean government [NRF-2018R1A4A1024713, NRF-2019R1A2C2004925]
- National Research Foundation of Korea (NRF) [NRF-2017H1A2A1045655]
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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.
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