Visible Light and Triselenium Dicyanide (TSD): New Horizons in the Synthesis of Organic Selenocyanates

Abstract

Herein we describe a new method for the synthesis of α‐carbonyl selenocyanates by reacting triselenium dicyanide (TSD) and styrenes under blue light irradiation and O2 atmosphere. The reactions are triggered by the formation of Se‐centered radical species, followed by the addition/oxidation of the styrene π‐bond. α‐Carbonyl selenocyanates and α‐hydroxy selenocyanates were obtained in moderate to excellent yields from aryl‐ and alkyl‐substituted alkenes, respectively. It was demonstrated that α‐carbonyl selenocyanates could be used as a synthetic platform in a multicomponent reaction strategy to prepare 2‐phenylimidazo[1,2‐a]pyridine derivatives, which were evaluated for their photophysical properties. Overall, this new method provides a useful tool for synthesizing α‐carbonyl selenocyanates, demonstrating their potential for use in the synthesis of other compounds, and opening new synthetic opportunities to construct organic selenocyanate compounds.

TBA(FeCl3Br) Complex as a Photocatalyst in the Csp3–H Bond Activation in Alcohols for the Synthesis of N-Based Heterocycles

“…Thus, in line with our recent interest in the development of visible-light-mediated ecofriendly approaches, − we disclose herein the Fe­(III)-photocatalyzed C sp3 –H bond activation in benzyl and alkyl alcohols, allowing the selective synthesis of 2-substituted BCZ and 2-substituted QZN, under blue-light irradiation (Scheme ).…”