Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Abstract

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Radical–anion coupling through reagent design: hydroxylation of aryl halides

“…Arene hydroxylation reactions are powerful enabling synthetic methods which are routinely used in the preparation of high-value pharmaceuticals, agrochemicals, polymers and natural products. 1 Many different synthetic approaches have been developed to form aryl C(sp 2 )–OH bonds, 2 but in terms of cost, operational simplicity and toxicity, nucleophilic aromatic substitution (S N Ar) 3 represents one of the most attractive and frequently used methods. 4 However, the broad application and selectivity of this approach is limited by the high basicity and low nucleophilicity of the hydroxide anion.…”

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

“…The study indicated that the reaction does not involve any possible hydrogen peroxide radicals, such as hydroxyl radical, peroxy hydroxyl radical, and superoxide radical [34] . A plausible mechanism for the reaction has been proposed based on the previously reported literature [32] . The transformation of boronic acid II to phenol V was accelerated rapidly by forming boronic acid adduct III with activated hydrogen peroxide complex I , which further undergoes rearrangement to give intermediate compound IV and final hydrolysis yielded phenol V (see Supporting information, Figure S1) [34] …”

“…Earlier reported protocol for the synthesis of benzofuranone ( 9 u ) utilizes a stoichiometric amount of catalyst, required elevated temperature, and resulted in a relatively lower yield (Figure 2B) [30] . The synthesis of a protein disulfide isomerase inhibitor derivative of menthol ( 2 aa ) was accomplished in 86 % yield by using the developed protocol, whereas the previously developed protocol utilized UV light irradiation over 24 h in the presence of molecular O 2 and provided comparatively lower yield (69 %) of the desired product (Figure 2C) [31,32] …”

Peripheral or nonperipheral tetra‐[4‐(9H‐carbazol‐9‐yl)phenoxy] substituted cobalt(II), manganese(III) phthalocyanines: Synthesis, acetylcholinesterase, butyrylcholinesterase, and α‐glucosidase inhibitory effects and anticancer activities

“…The synthetic routes of 4‐[4‐(9 H ‐carbazol‐9‐yl)phenoxy]phthalonitrile (P‐CN), 3‐[4‐(9 H ‐carbazol‐9‐yl)phenoxy]phthalonitrile (N‐CN) and metallophthalocyanines (PCo, PMn, NCo, and NMn) have been shown in Figure 1. 4‐[4‐(9 H ‐Carbazol‐9‐yl)phenoxy]phthalonitrile, 3‐[4‐(9 H ‐carbazol‐9‐yl)phenoxy]phthalonitrile were prepared by the reaction between 4‐(9 H ‐carbazol‐9‐yl)phenol [ 38 ] 1 and 4‐nitrophthalonitrile, 3‐nitrophthalonitrile. Then, peripheral or nonperipheral tetra‐[4‐(9 H ‐carbazol‐9‐yl)phenoxy] substituted cobalt(II), manganese(III) phthalocyanines (PCo, PMn, NCo, and NMn) were synthesized by a cyclotetramerization reaction of the 4‐[4‐(9 H ‐carbazol‐9‐yl)phenoxy]phthalonitrile (P‐CN), 3‐[4‐(9 H ‐carbazol‐9‐yl)phenoxy]phthalonitrile (N‐CN).…”