期刊
CHEMICAL SCIENCE
卷 10, 期 22, 页码 5832-5836出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc01370a
关键词
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资金
- EPSRC Dial-a-Molecule Network [EP/P007589/1]
- Elsevier
- EPSRC [EP/P007589/1] Funding Source: UKRI
Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of alpha-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.
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