Three-Component syn-Carbosulfenylation of Alkene Through Reagent Design – Pre-Print Now Online

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 SN2 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: