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Dalton transactions (Cambridge, England : 2003)

Addition of boranes to N-aryl-salicylaldimines: intramolecular hydrogenation of imines.


PMID 21431160

Abstract

Addition of boranes to N-aryl-salicylaldimines takes place initially at the reactive phenolic O-H bond to give an activated boron-containing imine and dihydrogen. In some cases a subsequent intramolecular hydrogenation step is observed and the C=N imine bond is reduced to the corresponding amine. Reactions with dimesitylborane in THF are unique in that the reduced amine product is the major product observed in solution.

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