Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 24, Pages 8951-8964Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500970
Keywords
boron; chemoselectivity; cross-coupling; palladium; speciation
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Funding
- Engineering and Physical Sciences Research Council (EPSRC)
- GlaxoSmithKline
- Engineering and Physical Sciences Research Council [1628052] Funding Source: researchfish
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Boronic acid solution speciation can be controlled during the Suzuki-Miyaura cross-coupling of haloaryl N-methyliminodiacetic acid (MIDA) boronic esters to enable the formal homologation of boronic acid derivatives. The reaction is contingent upon control of the basic biphase and is thermodynamically driven: temperature control provides highly chemoselective access to either BMIDA adducts at room temperature or boronic acid pinacol ester (BPin) products at elevated temperature. Control experiments and solubility analyses have provided some insight into the mechanistic operation of the formal homologation process.
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