Photo-tunable oxidation of toluene and its derivatives catalyzed by TBATB

Photoinduced oxidation of benzylic boronic esters to ketones/aldehydes via α-borylalkyl radicals

“…The reaction began with taking away the benzylic hydrogen atom from 2a by the bromine radical (Br˙), which originated from the homolytic cleavage of Br–Br bonds in TBATB under illumination. 16 Under the oxygen atmosphere, the α-borylbenzyl radical IM1 would trap one O 2 to generate peroxyl radical IM2 . Then, IM2 and hydrogen bromide (HBr) underwent a hydrogen atom transfer (HAT) process to afford IM3 and regenerate the bromine radical (Br˙), thus completing the catalytic cycle.…”

Synthetic utility of biomimicking vanadium bromoperoxidase and n-tetrabutylammonium tribromide (TBATB) in organic synthesis

“…TBATB has been used for several important functional group transformations. 106–109 In 2006, Patel et al transformed various alcohols into esters through acylation using carboxylic acids (Scheme 30A). 106 The reaction was chemoselective in nature, where primary alcohols were chemoselectively acylated in the presence of secondary alcohols and phenols.…”

“…The controlled oxidation of toluene to aldehydes, ketones and carboxylic acids took place tuning the visible light (Scheme 30D). 109…”

“…TBATB has been used for several important functional group transformations. [106][107][108][109] In 2006, Patel et al…”

Highly Efficient One‐pot Aerobic Synthesis of α‐Aminophosphonate from Alcohols: Dual Catalytic Effect of Tetrabutylammonium Tribromide (TBATB)

“…[28][29][30][31][32][33][34] Very recently, we presented TBATB as an agent for alcohol and toluene oxidation under visible blue light irradiation (465 nm) under mild and green conditions. [18,35] According to our knowledge, to date, there are two reports on the synthesis of one-pot α-aminophosphonates from benzyl alcohols: (a) the first work was done in 2017 by Kaboudin et al In this work, first imines were prepared through aerobic oxidation of alcohol in the presence of NaOH for 4 days at toluene using CuO@Fe 3 O 4 magnetic nanoparticles. Then diethylphosphite was added to the reaction mixture to synthesize αaminophosphonates at reflux condition for 1 day [36] (b) Dangroo et al reported in 2020, benzyl alcohols were first oxidized in the presence of ammonium perchlorate under UV light irradiation and triethylphosphite and amines were added to the reaction mixture to produce α-aminophosphenates (Scheme 1) [36] In continuing of our works in the photocatalytic aerobic oxidation of alcohols and synthesis of α-aminophosphonates, here in, we report the efficient two steps one-pot synthesis of α-aminophophonates from alcohols in the presence of TBATB.…”