期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 28, 页码 9503-9506出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05469
关键词
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资金
- National Science Foundation under the Center for Chemical Innovation in Selective C-H Functionalization [CHE-1205656]
- Novartis Pharmaceuticals
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1205646] Funding Source: National Science Foundation
The identification, optimization, and evaluation of a new catalytic protocol for sp(3) C-H hydroxylation is described. Reactions are performed in aqueous acid using a bis(bipyridine)Ru catalyst to enable oxidation of substrates possessing basic amine functional groups. Tertiary and benzylic C-H hydroxylation is strongly favored over N-oxidation for numerous amine derivatives. With terpene-derived substrates, similar trends in reactivity toward tertiary and benzylic C-H bonds are observed. Hydroxylation of chiral tertiary centers is enantiospecific in spite of the ionizing strength of the reaction medium. Preliminary kinetics experiments show a marked difference in reactivity between isomeric cis- and trans-Ru catalysts suggesting that the catalyst is configurationally stable under the reaction conditions.
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