Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-pot Formal Dehydroboration Sequence

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 ortho-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.

Automated summary

In this study, a one-pot reaction involving diaryliodonium and aryne intermediates is used to substitute the boron group and ortho-hydrogen atom in arylboron compounds. The method demonstrates the versatility of arylboron reagents and arynophiles, and is applied to the formal synthesis of a potential drug candidate.