The sensitivity of single-particle fluorescence microscopy uniquely enables direct observation of the buildup and the persistence of organozinc intermediates in various reaction conditions. When combined with NMR spectroscopy, these imaging data give insight into the previously elusive mechanistic details in the synthesis of widely used organozinc reagents. These findings characterize the acceleration of oxidative addition of the starting organohalide to the surface of zinc metal in differing conditions. These findings characterize the acceleration of oxidative addition of the starting organoiodide to the surface of zinc metal in DMSO relative to THF, but once formed, surface intermediates display similar persistence in either solvent. In addition, a solution species of the organozinc synthesized with DMSO was characterized indicating a different coordination environment when using DMSO vs THF. The current studies are a demonstration of a highly sensitive, single-particle fluorescence microscopy technique to pinpoint otherwise elusive mechanistic effects in synthetic chemistry.

Determination of organozinc complexes structure and reactivity by combined microscopy and NMR spectroscopy

ACS Spring 2022

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