期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 2, 页码 624-627出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja311669p
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资金
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM62871]
- Merck Research Laboratories
The first Suzuki cross-couplings of unactivated tertiary alkyl electrophiles are described. The method employs a readily accessible catalyst (NiBr2 center dot diglyme/4,4'-di-tert-butyl-2,2'-bipyridine, both commercially available) and represents the initial example of the use of a group 10 catalyst to cross-couple unactivated tertiary electrophiles to form C-C bonds. This approach to the synthesis of all-carbon quaternary carbon centers does not suffer from isomerization of the, alkyl group, in contrast with the umpolung strategy for this bond construction (cross-coupling of a tertiary alkylmetal with an aryl electrophile). Preliminary mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.
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