Abstract
Language | English |
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Number of pages | 5 |
Journal | Angewandte Chemie International Edition |
Publication status | Accepted/In press - 2 Dec 2016 |
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Keywords
- multinucleophile systems
- chemical synthesis
- chemoselectivity
- organoborons
- arylboron nucleophiles
- transmetallation
- kinetic discrimination
- Suzuki-Miyaura reaction
- boron
- cross-coupling
- palladium
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Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. / Fyfe, James W. B.; Fazakerley, Neal J.; Watson, Allan J. B.
In: Angewandte Chemie International Edition, 02.12.2016.Research output: Contribution to journal › Article
TY - JOUR
T1 - Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation
AU - Fyfe, James W. B.
AU - Fazakerley, Neal J.
AU - Watson, Allan J. B.
N1 - This is the peer reviewed version of the following article: Fyfe, J. W. B., Fazakerley, N. J., & Watson, A. J. B. (2016). Chemoselective Suzuki-Miyaura cross-coupling via kinetic transmetallation. Angewandte Chemie International Edition, which will be published in final form at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
PY - 2016/12/2
Y1 - 2016/12/2
N2 - 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.
AB - 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.
KW - multinucleophile systems
KW - chemical synthesis
KW - chemoselectivity
KW - organoborons
KW - arylboron nucleophiles
KW - transmetallation
KW - kinetic discrimination
KW - Suzuki-Miyaura reaction
KW - boron
KW - cross-coupling
KW - palladium
UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773
M3 - Article
JO - Angewandte Chemie International Edition
T2 - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
ER -