The deuterium kinetic isotope effect has long been exploited extensively by physical organic chemists for studying reaction mechanisms and medicinal chemists for studying metabolism of deuterated versions of drugs respectively.  Benzaldehydes are important building blocks in synthetic organic chemistry that have wide applications for the synthesis of natural products and pharmaceutical drugs. Herein we report a general synthetic methodology for the synthesis of highly functionalized deuterated benzaldehydes in 100 % isotopic purity via regio-selective deutero-formylation. Regio-selective deprotonation of 1,3- disubstituted benzene 1  with LDA at -78 oC and treatment with d7-DMF led to the synthesis of 2-deutero-1, 3-disubstituted benzaldehydes 2  in moderate to good yields. The synthetic methodology described represents a simple yet versatile route to functionalized formyl-deuterated benzaldehydes.

Synthesis of novel formyl-deuterated benzaldehydes via regio-selective deutero-formylation

243rd National Meeting (2012)

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