Visible‐Light‐Induced Hydroxysulfurization and Alkoxysulfurization of Styrenes in the Absence of Photocatalyst: Synthesis of β‐Hydroxysulfides and β‐Alkoxysulfides

Abstract

We developed hydroxysulfurization and alkoxysulfurization of styrenes using a visible‐light synthetic strategy in the absence of photocatalyst and oxidant. This strategy provided the corresponding β‐hydroxysulfides and β‐alkoxysulfides in moderate to good yields with high regioselectivity. The reaction was tolerated by a wide range of functional groups. This is the first example of ArSSAr/CBr4 system has been introduced into organic transformation.

Visible‐Light‐Induced Difunctionalization of Styrenes: An Efficient and Green Protocol for the Synthesis of β‐Acyloxyselenides

“…On the basis of the above experimental results and previous works, [19] a possible mechanism has been depicted in Scheme 4. Initially, the excited-state Rose Bengal* (RB*) was generated from Rose Bengal (RB) under the light irradiation of a blue LED.…”

Alkoxysulfenylation of alkenes: development and recent advances

“…Recently, Meng and Wang along with their co-workers demonstrated the similar alkoxysulfenylation under visible light irradiation and photocatalyst-free conditions. 21 The transformation was performed in DCM at room temperature by using the combination of blue LED and carbon tetrabromide (CBr 4 ). Under these conditions several styrene derivatives 9 carrying various substituents were slowly converted to the corresponding β-alkoxy sulfides 12 in moderate to good yields by treatment with diaryl disulfides 10 and diols 11 ( Scheme 3b ).…”

Visible‐light‐Induced Sulfhydrylation and Oxylation of Olefins with Iodine as Catalyst

“…Of course, the photoreaction without photosensitizer can also be carried out. Wang [24] groups reported visible‐light‐induced hydroxysulfurization and alkoxysulfurization of styrenes to achieve the β ‐oxy sulfides compounds promoted by CBr 4 (Scheme 1b). Although the use of transition metal complexes and organic dyes was avoided, the equivalent CBr 4 still brought too much toxicity.…”