Addition of boranes to N-aryl-salicylaldimines: intramolecular hydrogenation of imines |
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Authors: | Barnes Stephanie S Vogels Christopher M Decken Andreas Westcott Stephen A |
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Institution: | Department of Chemistry and Biochemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada. |
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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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