Am ethodf or the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl 2 (PPh 3 ) 3 ]a nd D 2 Oa sadeuterium source is presented. Throughv ariation of additives like CuI, KOH, and various amounts of zinc powder,o rthogonal chemoselectivities in the deuteration process are observed.M echanistic investigation indicates the presence of different, defined Rucomplexes under the given specific conditions. Scheme1.Activation of the precatalyst [RuCl 2 (PPh 3 ) 3 ]( 1)t hrough additives. Scheme2.Additive-directed chemoselective reductive deuteration of carbonylc ompounds and alkynes.[ a] 16 hreactiont ime.
We describe the iron-catalyzed reductive cleavage of N–O-bonds in oxazines using malononitrile as reductant, which – in sequence with a [4 + 2]-cycloaddition – can be considered as an efficient way for the diastereoselective 1,4-aminohydroxylation of 1,3-dienes.
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