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Competition studies in alkyne electrophilic cyclization reactions.

ABSTRACT: 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), ICl, 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.

SUBMITTER: Mehta S

PROVIDER: S-EPMC2662397 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Competition studies in alkyne electrophilic cyclization reactions.

Mehta Saurabh S Waldo Jesse P JP Larock Richard C RC

The Journal of organic chemistry 20090201 3

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), ICl, 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 in ...[more]

PMID: 19105638

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