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

Abstract

The scope of biomimicking vanadium bromoperoxidase in producing bromonium ions and its further utilisation in conducting oxidative bromination or cleavage of various organic molecules has been described in this review.

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

“…The investigation was initiated by exploring the reaction of (1-phenylethyl)boronic pinacol ester 1a in the presence of bromine radical donor TBATB, which was a shelf-stable and involatile solid, and also cheap and readily available. 15 Fortunately, preliminary attempts led to the formation of the target product acetophenone 2a , under irradiation of visible-light and an O 2 atmosphere.…”

Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System

“…By biomimicking, various organic tribromides have been synthesized and applied to achieve the same effect. Among these, n-tetrabutylammonium tribromide (TBATB), a low-cost, shelf-stable, and volatile-free solid, has been investigated as the bromination reagent or surrogate of HBr, allowing for an array of stoichiometric or catalytic transformations. This approach detours the manipulation of toxic, corrosive, and volatile molecular bromine and reduces the environmental impact of the reactions .…”

Electrochemical transformations catalyzed by cytochrome P450s and peroxidases

“…lignin peroxidase, 47,48,[51][52][53][54][55][56] horseradish peroxidase (HRP), 46,[57][58][59][60] chloroperoxidase (CPO), [61][62][63][64] manganese peroxidase, 65,66 and haloperoxidases. [67][68][69] have been used extensively in biocatalytic oxidations (e.g., the oxidation of alkanes to alcohols) or chromogenic reactions in chemiluminescence. 70 While oxidation of these enzymes by H 2 O 2 is required, their inactivation by H 2 O 2 may limit their use in industry.…”

“…lignin peroxidase, 47,48,51–56 horseradish peroxidase (HRP), 46,57–60 chloroperoxidase (CPO), 61–64 manganese peroxidase, 65,66 and haloperoxidases. 67–69 have been used extensively in biocatalytic oxidations ( e.g. , the oxidation of alkanes to alcohols) or chromogenic reactions in chemiluminescence.…”