期刊
ORGANIC LETTERS
卷 17, 期 19, 页码 4906-4909出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02481
关键词
-
资金
- National Science Foundation [CHE 1111406]
- National Science Foundation (IRD)
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1639875] Funding Source: National Science Foundation
Metalated nitriles exhibit complementary chemoselectivities in electrophilic alkylations. N-Lithiated or C-magnesiated nitriles can be prepared from the same nitrile precursor and selectively reacted with a 1:1 mixture of methyl cyanoformate and benzyl bromide or bifunctional electrophiles through chemoselective attack onto either an alkyl halide or a carbonyl electrophile. A mechanistic explanation for the chemoselectivity preferences is provided that rests on the structural and complexation differences between N- and C-metalated nitriles.
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