[en] Rhodium (II) carboxylates of perfluoroacids are very efficient catalysts for promoting the insertion of carbenes (carbenoids) (generated from diazoesters) into the C-H bonds of alkanes with selectivities which differ from those observed in typical free-carbene processes.
Disciplines :
Chemistry
Author, co-author :
Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Noels, Alfred ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Hubert, André J.
Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Language :
English
Title :
Transition-metal-catalysed reactions of diazoesters. Insertion into C-H bonds of paraffins by carbenoids
Publication date :
1981
Journal title :
Journal of the Chemical Society. Chemical Communications
The influence of the diazoester alkoxy-group was previously evidenced in carbene cycloadditions to olefins, see A. J. Hubert, A. F. Noels, A. J. Anciaux, and Ph. Teyssié, Synthesis, 1976, 600
A. J. Hubert, A. F. Noels, A. J. Anciaux, and Ph. Teyssié, J. Org. Chem., 1980, 45, 695.
A. J. Anciaux, A. Demonceau, A. T. Hubert, A. F. Noels, and Ph. Teyssié, J. Chem. Soc., Chem. Commun., 1980, 765
A. J. Anciaux, A. Demonceau, A. T. Hubert, A. F. Noels, and Ph. Teyssié, J. Org. Chem., 1981, 46, 873.
For a comparison with copper catalysts, see L. T. Scott and G. J. Decicco, J. Am. Chem. Soc., 1974, 96, 322.
D. S. Wulfman and B. Poling, ‘Reactive Intermediates,’ ed. R. A. Abramovitch, Plenum Press, New York, 1980, Vol. 1, p. 431
A. P. Marchand and N. McBrockway, Chem. Rev., 1974, 74, 431
W. Kirmse, ‘Carbene Chemistry,’ 2nd Edn., Academic Press, New York, 1971, pp. 85-88 and p. 209.
