A mechanistic study on modern palladium catalyst precursors as new gateways to Pd(0) in cationic Heck reactions |
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Authors: | Andreas Svennebring Mats Larhed |
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Affiliation: | a Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University, PO Box 574, SE-751 23 Uppsala, Sweden b Department of Physical and Analytical Chemistry, Uppsala Biomedical Center, Uppsala University, PO Box 599, SE-751 23 Uppsala, Sweden |
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Abstract: | Electrospray ionization mass spectrometry (ESI-MS) was used as a means to directly identify catalytic cationic organopalladium species in ligand-controlled Heck reactions involving electron-rich olefins and different Pd-sources. In these high-temperature Heck arylations, the oxidative addition intermediates were observed as bidentate ligand chelated cationic aryl palladium species, suggesting that the used ligand attaches to the metal center at the very beginning of the catalytic cycle. This was also in agreement with the obtained regioisomeric profile of the isolated products. The investigation supports the standard Pd(0)/Pd(II) Heck mechanism and provides further insight regarding the conceivable composition of fundamental Pd(II) intermediates in an ongoing Heck reaction. |
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Keywords: | ESI-MS Heck Palladium Microwave |
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