期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 3, 页码 1141-1147出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo802196r
关键词
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资金
- National Institute of General Medical Sciences [GM070620, GM079593]
- National Institutes of Health Kansas University Center of Excellence for Chemical Methodologies and Library Development [P50 GM069663]
The relative reactivity of various functional groups toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I-2, ICI, NBS and PhSeCl as electrophiles. The results indicate that the nucleophilicity of the competing functional groups, polarization of the alkyne triple bond, and the cationic nature of the intermediate are the most important factors in determining the outcome of these reactions.
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