Oxidative homocoupling of aryl, alkenyl, and alkynyl Grignard reagents with TEMPO and dioxygen

MS Maji, T Pfeifer, A Studer

Index: Maji, Modhu Sudan; Pfeifer, Thorben; Studer, Armido Angewandte Chemie - International Edition, 2008 , vol. 47, # 49 p. 9547 - 9550

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Citation Number: 92

Abstract

The treatment of various alkyl organometallic compounds RÀM (M= Li, Mg, Zn, Cu, Sm, Ti) with 2 equivalents of 2, 2, 6, 6-tertramethylpiperidine-N-oxyl radical (TEMPO) has been reported to lead to the corresponding alkoxyamines TEMPO–R.[1] In these processes, one equivalent of TEMPO is required for oxidation of the organometallic species to the corresponding C-centered radical, which is subsequently trapped by the second ...