期刊
NATURE CHEMISTRY
卷 11, 期 2, 页码 117-122出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/s41557-018-0181-x
关键词
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资金
- EPSRC [EP/I038071/1]
- H2020 ERC [670668]
- Bayer Science and Education Foundation
- BBSRC [BB/F011539/1] Funding Source: UKRI
- EPSRC [EP/I038071/1, EP/L011999/1, EP/K03927X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
Transition-metal-catalysed cross-coupling reactions, particularly those mediated by palladium, are some of the most broadly used chemical transformations. The fundamental reaction steps of such cross-couplings typically include oxidative addition, transmetallation, carbopalladation of a pi-bond and/or reductive elimination. Herein, we describe an unprecedented fundamental reaction step: a C-C sigma-bond carbopalladation. Specifically, an aryl palladium(II) complex interacts with a sigma-bond of a strained bicyclo[1.1.0]butyl boronate complex to enable addition of the aryl palladium(II) species and an organoboronic ester substituent across a C-C sigma-bond. The overall process couples readily available aryl triflates and organoboronic esters across a cyclobutane unit with total diastereocontrol. The pharmaceutically relevant 1,1,3-trisubstituted cyclobutane products are decorated with an array of modular building blocks, including a boronic ester that can be readily derivatized.
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