Journal of Organometallic Chemistry p. 379 - 390 (1985)
Update date:2022-09-26
Topics:
Wakita, Yoshiaki
Noma, Shun-Ya
Maeda, Minoru
Kojima, Masaharu
Lithium bis(carbamoyl)cuprates (2) were readily derived from secondary amines such as N-methylaniline, N-methylbenzylamine, and diethylamine, under mild carbonylation conditions (0 deg C, 1 atm of carbon monoxide), but diphenylamine and benzylphenylamine were unsuitable as the starting materials.The carbamoylcopper complexes 2 formed in ether were readily converted to the corresponding formamides, oxamides, carbamates, and oxamic acids by the appropriate treatment.The formation and stability of 2 depended much on the solvent used.The higher polarity effect of the solvent (DME, THF, and HMPA) made 2 less stable and caused concomitant evolution of carbon monoxide in further reactions.A palladium catalyst was found to be effective for cross-coupling reactions of 2 with iodobenzene or (E)-β-bromostyrene.
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