Chemoselective Suzuki–Miyaura Cross‐Coupling via Kinetic Transmetallation

Chemoselective Suzuki–Miyaura Cross‐Coupling via Kinetic Transmetallation

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 discr...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 56; no. 5; pp. 1249 - 1253
Main Authors: Fyfe, James W. B., Fazakerley, Neal J., Watson, Allan J. B.
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 24-01-2017
Edition:International ed. in English
Subjects:
Acids
boron
chemoselectivity
Couplings
Cross coupling
Deactivation
Esters
palladium
Protecting groups
transmetallation
transmetallation
cross-coupling
chemoselectivity
palladium
boron
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Summary: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 cross‐couplings in a single operation in the absence of protecting groups. Set phases to stun: Chemoselective Suzuki–Miyaura cross‐coupling can be achieved by kinetic discrimination of boronic acids and BPin esters during transmetallation. Simultaneous electrophile control allows sequential chemoselective cross‐couplings in a single operation in the absence of protecting groups.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201610797