Abstract
AbstractA new and practical α‐monomethylation strategy using an amine‐borane/N,N‐dimethylformamide (R3N‐BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α‐monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N‐BH3 donated the remaining two hydrogen atoms. Such a unique reaction pathway enabled controllable assemblies of CDH2‐, CD2H‐, and CD3‐ units using Me2NH‐BH3/d7‐DMF, Me3N‐BD3/DMF and Me3N‐BD3/d7‐DMF systems, respectively. Further application of this method to the facile synthesis of anti‐inflammatory flurbiprofen and its varied deuterium‐labeled derivatives was demonstrated.
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