Abstract
Lithium bis(carbamoyl)cuprates ( 2) were readily derived from secondary amines such as N-methylaniline, N-methylbenzylamine, and diethylamine, under mild carbonylation conditions (0°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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