Journal
CHEMSUSCHEM
Volume 12, Issue 24, Pages 5265-5273Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201902853
Keywords
base; cross-coupling; palladium; sustainable chemistry; water
Funding
- National Natural Science Foundation of China [21771122, 21571121, 21701108, 21602129]
- National Key Research and Development Program of China [2016YFB0701100]
- Natural Science Foundation of Shaanxi Provincial Department of Education [2018JQ2012]
- China Postdoctoral Science Foundation [2017M623110]
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A simple and efficient system was developed for the ligand-free Pd-catalyzed Suzuki-Miyaura reaction in water under mild conditions. Quaternary ammonium hydroxides with long chains were found to be very suitable bases. This ligand-free Pd-catalyzed Suzuki-Miyaura reaction showed improved durability in water with Pd loadings decreased to ppm level. Bases were shown to stabilize active palladium species in addition to acting as a base during the catalytic process. In the catalytic system with a strong base, the soluble active Pd-II ion exhibited anti-reduction properties, which prevented aggregation and deactivation of Pd species. The entire catalytic system could be recycled after separating the product by simple filtration. The water-compatible and air-stable effective catalytic protocol described herein represents an attractive and green synthetic advance in Suzuki-Miyaura couplings.
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