Reactions which can manipulate the connectivity of the molecular skeleton are powerful tools for late-stage functionalization and enable unique synthetic routes, but their implementation has been hindered in part by their often non-intuitive retrosynthetic logic. This presentation will cover newly discovered transformations from our laboratory which enable single-atom changes to aliphatic and aromatic heterocycles through the insertion and deletion of single heavy atoms (C,N,O, etc.) from ring systems. These powerful new transformations are accomplished through a variety of strategic approaches spanning organic chemistry, organometallic chemistry, and photochemistry. Applications to late-stage functionalization and diversification of complex pharmaceutically-relevant compounds and unique opportunities for synthesis will be presented.

Advancing single atom logic for skeletal editing of heterocycles

ACS Spring Meeting 2021

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