TY - JOUR
T1 - The Cu(i) catalyzed Meerwein reaction in aqueous solutions proceeds via a radical mechanism. the effect of several ligands
AU - Burg, Ariela
AU - Wolfer, Yaniv
AU - Kornweitz, Haya
AU - Shenar-Jackson, Limor
AU - Masarwa, Alexandra
AU - Meyerstein, Dan
PY - 2013/4/14
Y1 - 2013/4/14
N2 - The effect of the ligands 2,5,8,11-tetramethyl-2,5,8,11-tetraaza-dodecane and fumarate on the mechanism and kinetics of the Cu(i) catalyzed Meerwein reaction was studied. The results point out that initially the Cu(i) ion binds to the aromatic ring with the diazo substituent. This reaction is followed by a redox process involving N2 loss and the formation of an aryl radical, R. The following kinetics depends on the nature of the ligand, its effect on the redox potential and the steric hindrance it induces on the central copper ion. Clearly the ligand 2,5,8,11-tetramethyl-2,5,8,11-tetraaza-dodecane does not form an optimal catalyst with Cu(i) while it does for the Ullmann reaction.
AB - The effect of the ligands 2,5,8,11-tetramethyl-2,5,8,11-tetraaza-dodecane and fumarate on the mechanism and kinetics of the Cu(i) catalyzed Meerwein reaction was studied. The results point out that initially the Cu(i) ion binds to the aromatic ring with the diazo substituent. This reaction is followed by a redox process involving N2 loss and the formation of an aryl radical, R. The following kinetics depends on the nature of the ligand, its effect on the redox potential and the steric hindrance it induces on the central copper ion. Clearly the ligand 2,5,8,11-tetramethyl-2,5,8,11-tetraaza-dodecane does not form an optimal catalyst with Cu(i) while it does for the Ullmann reaction.
UR - http://www.scopus.com/inward/record.url?scp=84875045767&partnerID=8YFLogxK
U2 - 10.1039/c3dt32573c
DO - 10.1039/c3dt32573c
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C2 - 23389299
AN - SCOPUS:84875045767
SN - 1477-9226
VL - 42
SP - 4985
EP - 4993
JO - Dalton Transactions
JF - Dalton Transactions
IS - 14
ER -