Cross-coupling followed by desilylation of terminal alkynes is a common method for building complexity in organic synthesis. In the course of other studies, our work required deuterium enriched ethynylpyridines. Replacement of the trimethylsilyl group with a deuterium atom can be difficult to complete with many current desilylation techniques. We will discuss the first reported one-pot microwave assisted desilylation and deuterium incorporation of ethynyl pyridines. Using tetrabutylammonium fluoride and deuterium oxide, we observe rapid reactions with high deuterium incorporation for various ethynyl substituted pyridines.

Desilylation and deuterium enrichment of ethynyl substituted pyridines

249th National Meeting (2015)

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