Traditional carbene chemistry utilizes explosive diazo species and unstable <i>gem</i>-dihalo compounds. While strategies have been developed to address the safety of carbene precursors, non-stabilized alkyl carbenes remain not fully harnessed for catalytic carbene chemistry. We have discovered that alkyl, aryl, and formyl aldehydes can be readily converted to electronically diverse carbenoid species via α-acyloxy halides. Employing these carbenoid species, we can access traditional carbene reactivity while providing a safer reaction profile than diazo-based carbene reactivity. This allows multigram, batch reactions to occur without any additional precautions.

Non-diazo carbene reactivity from aldehydes

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.