Dithioacetalization or thioetherification of benzyl alcohols using 9-mesityl-10-methylacridinium perchlorate photocatalyst

Abstract

We report herein the use of 9-mesityl-10-methylacridinium perchlorate as the visible-light photocatalyst for dithioacetalization or thioetherification of benzyl alcohols in one pot using aerial dioxygen as terminal oxidant. EPR analysis...

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

“…With the advantages of photocatalysis in mind, we turned our attention to the influence of visible light on the oxidative cyclization of 2-aminobenzyl alcohol ( 1a ) and 1-phenylethan-1-ol ( 2a ) (Table ). Given that the indirect Friedlander reaction generally involves the oxidation of alcohols, we first examined the photocatalysts that were reportedly employed for this class of oxidative transformations (entries 1–6), including Rose Bengal, Eosin Y, [Mes-Acr] + ClO 4 – , thioxanthenone, 9-fluorenone, and sodium trifluoromethanesulfinate . Among them, [Mes-Acr] + ClO 4 – and 9-fluorenone showed activity under our reaction conditions (entries 3 and 5).…”

A Click Reaction Enabled by Phosphorus‐Oxygen Bond for Synthesis of Triazoles

“…Further, EPR experiments (Figure 5) also helped to establish the radical mechanism. [28] When phenyl propiolate derivative (2 f), phosphoryl azidate in DMSO (1 mL) was heated for 2 h at 90°C in presence of 0.5 mL of a spin trapping agent 5,5dimethyl-1-pyrroline-N-oxide (DMPO), a new signal was ob-served (Figure 5a). This implied that azidyl radical have formed and trapped by DMPO which forms a stable DMPO-N 3 radical.…”

Visible Light as the Key for the Formation of Carbon–Sulfur Bonds in Sulfones, Thioethers, and Sulfonamides: An Update

“…84 Mes-MeAcr-ClO4 was also exploited as the photocatalyst in an oxidative dithioacetalization or thioetherification of benzyl alcohols 171, using a 3 W blue LED light at room temperature. 85 Thiophenols 162 were used as the substrates and the reaction was addressed…”

“…In 2020, Mal also used Mes-MeAcr-ClO 4 as the photocatalyst in an oxidative dithioacetalization or thioetherification of benzyl alcohols 171, using a 3-W blue LED light at room temperature (Scheme 60). 85 Thiophenols 162 were used as the substrates and the reaction examined the synthesis of sulfides 175 versus thioacetals 174 in the case of para-electron-withdrawing substituted benzyl alcohols 171a. Mechanistically, benzaldehyde 172 is obtained from the corresponding benzyl alcohol 171 by the interaction of PC* and the alcohol via a SET.…”