A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.

Atropisomerism is a type of chirality that is ubiquitous but often overlooked in modern drug discovery. In this Account we discuss studies on leveraging atropisomerism as a design principle in medicinal chemistry, and how this work led to several seemingly disparate projects that began due to synthetic challenges associated with accessing pharmaceutically relevant atropisomers.

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