Competition studies in alkyne electrophilic cyclization reactions.
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.
Mehta
Saurabh
S
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Waldo
Jesse P
JP
Larock
Richard C
RC
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D001555:Benzene Derivatives; D006574:Heterocyclic Compounds, 2-Ring; D007097:Imines