Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-Pot Formal Dehydroboration Sequence
This work was supported by the National Science Foundation under Grant No. 2247802. The NSF provided instrument funding for the BioAnalytical Mass Spectrometry Facility at PSU under Grant No. 1828753.
Arylboron compounds are widely available and synthetically useful reagents in which the boron group is typically substituted. Herein, we show that the boron group and -hydrogen atom are substituted in a formal cycloaddition reaction. This transformation is enabled by a one-pot sequence involving diaryliodonium and aryne intermediates. The scope of arylboron reagents and arynophiles is demonstrated, and the method is applied to the formal synthesis of an investigational drug candidate.
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Karandikar, S. S., Metze, B. E., Roberts, R. A., & Stuart, D. R. (2023). Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-pot Formal Dehydroboration Sequence. Organic Letters.