期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 1, 页码 236-240出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408650
关键词
alkenes; high-valent palladium; nitrite; oxidation; oxygen
资金
- King Abdullah University of Science and Technology Centre in Development
- King Fahd University of Petroleum and Minerals
- NSF [CHE 1212767]
- NIH [R01GM031332]
- Gordon and Betty Moore Foundation
- NIH
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1502616, 1212767] Funding Source: National Science Foundation
Catalytic nitrite was found to enable carbon-oxygen bond-forming reductive elimination from unstable alkyl palladium intermediates, providing dioxygenated products from alkenes. A variety of functional groups were tolerated, and high yields (up to 94%) were observed with many substrates, also for a multigram-scale reaction. Nitrogen dioxide, which could form from nitrite under the reaction conditions, was demonstrated to be a potential intermediate in the catalytic cycle. Furthermore, the reductive elimination event was probed with O-18-labeling experiments, which demonstrated that both oxygen atoms in the difunctionalized products were derived from one molecule of acetic acid.
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