Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 5, Pages 1249-1253Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610797
Keywords
boron; chemoselectivity; cross-coupling; palladium; transmetallation
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Funding
- EPSRC
- GlaxoSmithKline
- Engineering and Physical Sciences Research Council [1628052] Funding Source: researchfish
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Chemoselective Suzuki-Miyaura cross-coupling generally requires a designed deactivation of one nucleophile towards transmetallation. Here we show that boronic acids can be chemoselectively reacted in the presence of ostensibly equivalently reactive boronic acid pinacol (BPin) esters by kinetic discrimination during transmetallation. Simultaneous electrophile control allows sequential chemoselective crosscouplings in a single operation in the absence of protecting groups.
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