Aryl and diaryl derivatives of alkyl- and benzyl-type carbamates were made by transmetalating the lithiated carbamates with zinc chloride, followed by a Negishi-type cross-coupling reaction with aryl halides. Asymmetric lithiation led to a lower than expected enantioselectivity, presumably due to racemization after transmetallation to palladium. Attempts to induce better enantioselectivity were performed using chiral palladium complexes as the coupling partner for the Negishi cross-coupling reaction with racemic zinc carbamates. The aryl carbamate derivatives can be reduced to mono- and diaryl alcohols, which are useful synthons in natual product synthesis.

Negishi-type cross-coupling arylation of selected carbamates

249th National Meeting (2015)

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