期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 25, 页码 8219-8226出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03989
关键词
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资金
- National Basic Research Program of China [2015CB856600]
- NSFC [21422206, 21272206]
- Fundamental Research Funds for the Central Universities
The synthesis of fluorinated complex molecules via direct C(sp(3))-H fluorination is attractive yet remains challenging. Here we describe the Pd(II)-catalyzed fluorination of unactivated methylene C(sp(3))-H bonds by an inner-sphere mechanism. This method allows the site- and diastereoselective fluorination of beta-methylene C(sp(3))-H bonds of alpha-amino acid derivatives. A range of substrates containing both aliphatic and benzylic C(sp(3))-H bonds were compatible with this protocol, leading to an array of beta-fluorinated alpha-amino acids. Stoichiometric fluorination of an isolated palladacycle intermediate takes place rapidly under very mild reaction conditions (room temperature, 5-10 min). Data from preliminary mechanistic studies are consistent with direct C-F reductive elimination from a high-valent intermediate.
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