Suggestion of an organometallic intermediate in an intramolecular dechlorination reaction involving copper(I) and a ArCH2Cl moiety |
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Authors: | Maiti Debabrata Narducci Sarjeant Amy A Itoh Shinobu Karlin Kenneth D |
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Institution: | Department of Chemistry, The Johns Hopkins University, Baltimore, Maryland 21218, USA. |
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Abstract: | A copper(I)-mediated reductive dechlorination reaction involving an "internal" chloromethylene substrate at the pyridyl 6-position of one TMPA arm (TMPA triple bond TPA triple bond tris(2-pyridylmethyl)amine) leads to a 1:1 ratio of the starting ligand 6ClCH2-TMPA and a new methyl-TMPA product, 6CH2H-TMPA. On the basis of observed product distributions and a kinetic study, a reaction mechanism involving intramolecular oxidative insertion of Cu(I) to the C-Cl substrate is suggested. The resulting organometallic intermediate is then protonated, leading to the observed products. |
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