We’ve recently started exploring foreign parts of the periodic table, and turned our attention to sulfur. Organosulfur compounds are useful in various settings, and three-component couplings represent a fast, efficient, and modular way to synthesize such compounds. Classical carbosulfenylation (the addition of a carbon and a sulfur(II) group across an alkene) proceed via a reactive thiiranium intermediate that is then opened in an S_N2 fashion, with limitations arising from the electrophilic nature of the sulfenyl transfer groups typically employed. We envisioned an alternative organometallic approach relying on three-component catalytic coupling of organoboron nucleophiles, sulfenyl electrophiles, and unactivated alkenes. This novel transformation was enabled by the discovery of a new family of N–S electrophiles that possess perfectly balanced reactivity, which could be understood through computational studies. Hats off to the team, graduate student co-authors Zi-Qi and Taeho, and former SURF intern Yilin, who has since returned to UCSB to finish her senior year of college.

For a link to the pre-print, click here: https://chemrxiv.org/engage/chemrxiv/article-details/61a7d3e0f35d4ca9794de71d