Introducing Alkyl Selenocyanates as Bifunctional Reagents in Photoredox Catalysis: Divergent Access to Ambident Isomers of −SeCN

Owing to their diverse biological activities and versatility as synthetic precursors, organoselonocyanes categorize themselves as vital compounds. However, a limited reagent pool restricts their utility. In the present work, alkyl selenocyanates are hereby established as new bifunctional reagents for the simultaneous transfer of an alkyl group in addition to −SeCN. These reagents, when merged with photocatalysis, provide a key to accessing organoselenocyanates from feedstock olefins in an efficient and atom-economic fashion. A route to the analogous isoselenocyanate isomers facilitated by Lewis acid catalysis is also reported, presenting a divergent strategy for accessing both ambident isomers of −SeCN in an efficient manner.