On the nature of organoindium intermediates: the formation of readily isolable difluoropropargylindium reagents and their regioselectivity towards electrophilic substitutions.
The structure and reactivity of intermediate propargylindium complexes have been investigated. Their reaction with electrophiles produced a difluoroalkyne or -allene, depending on the nature of the electrophiles. A mechanism based on the Curtin-Hammett principle was invoked to explain this phenomenon. A newly proposed mechanism on the formation of indium(III) complexes, through the intermediacy of indium(I) species, could help to explain the reaction of indium with 1,1,1-difluorobromo-2-alkynes in the presence of aldehydes.
Xu
Bo
B
Department of Chemistry, University of Louisville, Louisville, Kentucky, USA.
Hammond
Gerald B
GB
D004563:Electrochemistry; D005461:Fluorine / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D009019:Morphinans; C440369:N-propargyl; D009942:Organometallic Compounds; D007204:Indium; D005461:Fluorine