Organic synthesis with carbon monoxide: the synthesis of carbamoylstannanes and aromatic carbamoylation

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Abstract
The lithium salts of secondary amines were carbonylated and the carbamoyl-lithium species (1) produced quenched with ketones, alkyl halides and trialkyltin chlorides. The latter gave tributyl-, triphenyl- and trimethyl-carbamoylstannanes (2) in good yield. These were found to undergo palladium-catalysed cross coupling with aryl, alkenyl, and hetaryl halides (I, Br) to give the amides (4), (5), and (6) respectively, in fair to excellent yield, the trimethyl series being the reagents of choice.

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