57357-20-7

Usage

Uses

Used in Pharmaceutical Industry:
BIS(TERT-BUTYLCARBONYLOXY)IODOBENZENE 97 is used as a reagent for the preparation of α,β-unsaturated-γ-lactams via Rh-catalyzed C-H amination of allene carbamates, followed by Ru-catalyzed cyclocarbonylation. This process is essential in the synthesis of various pharmaceutical compounds.
Used in Chemical Synthesis:
BIS(TERT-BUTYLCARBONYLOXY)IODOBENZENE 97 is used as a catalyst in the palladium-catalyzed diamination process, which is crucial for the synthesis of various organic compounds.
Used in Heterocyclic Compound Synthesis:
In the field of organic chemistry, BIS(TERT-BUTYLCARBONYLOXY)IODOBENZENE 97 is used as a catalyst for the preparation of functionalized bicyclic heterocyclic compounds through rhodium-catalyzed allene amidation and cyclization.
Used in Copper-Catalyzed Intramolecular Aminoacetoxylation:
BIS(TERT-BUTYLCARBONYLOXY)IODOBENZENE 97 is used as a catalyst in the preparation of piperidine and pyrrolidine derivatives via copper-catalyzed intramolecular aminoacetoxylation of aminoolefins.
Used in C-H Acyloxylation of Arenes:
BIS(TERT-BUTYLCARBONYLOXY)IODOBENZENE 97 is employed as a catalyst in the C-H acyloxylation of arenes, a vital process in the synthesis of various aromatic compounds.
Used as a Hypervalent Iodine Oxidant:
BIS(TERT-BUTYLCARBONYLOXY)IODOBENZENE 97 is also used as a hypervalent iodine oxidant, playing a crucial role in various oxidation reactions in organic chemistry.

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 75-98-9 Trimethylacetic acid 
• 815-17-8 trimethylpyruvic acid 
• 591-50-4 iodobenzene 

Downstream Products

• 98-86-2 acetophenone 
• 1196712-45-4 5,5-dimethyl-1-tosylpiperidin-3-yl pivalate 
• 1196712-23-8 5-fluoro-3,3-dimethyl-1-tosylpiperidine 
• 1232693-12-7 C₂₂H₃₁NO₂Si 
• 1232693-15-0 C₂₃H₃₃NO₃Si 
• 1232693-17-2 (PivO)(Me)C₆H₃Si(iPr)2C₅H₄N 
• 1232693-20-7 C₂₃H₃₃NO₂Si 
• 1232693-24-1 C₂₄H₃₅NO₂Si 
• 1232693-28-5 C₂₂H₃₀ClNO₂Si 
• 1232693-27-4 C₂₂H₃₀FNO₂Si 
• 1232693-29-6 C₂₂H₃₀BrNO₂Si 
• 1232693-30-9 C₂₃H₃₂FNO₂Si 
• 1232693-31-0 C₂₃H₃₂ClNO₂Si 
• 1232693-32-1 C₂₉H₄₃NO₄Si 

Relevant academic research and scientific papers

A benzene-bridged divanadium complex-early transition metal catalyst for alkene alkylarylation with PhI(O2CR)2viadecarboxylation

The synthesis, structure and catalytic activity of a benzene-bridged divanadium complex were comprehensively studied. The reduction of (Nacnac)VCl2(1) (Nacnac = (2,6-iPr2C6H3NCMe)2HC) supported by β-diketiminate with potassium graphite (KC8) by employing benzene as the solvent allows access to the benzene-bridged inverted-sandwich divanadium complex (μ-η6:η6-C6H6)[V(Nacnac)]2(2a), which can catalyze alkene alkylarylation with hypervalent iodine(iii) reagents (HIRs)viadecarboxylation to generate regioselectively diverse indolinones. Furthermore, the mild nature of this reaction was amenable to a wide range of functionalities on alkenes and HIRs. Mechanistic studies revealed a relay sequence of decarboxylative radical alkylation/radical arylation/oxidative re-aromatization.

Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives

A visible-light-mediated decarboxylative tandem carbocyclization of acrylamide-tethered alkylidenecyclopropanes with phenyliodine(III) diacetate and various aliphatic acids has been reported in this paper. An alkyl radical in situ generated from phenyliodine(III) dicarboxylates upon visible-light irradiation catalyzed by fac-Ir(ppy)3 adds to the less hindered central carbon of alkylidenecyclopropane to initiate the tandem annulation, generating tetracyclic benzazepine derivatives in moderate to good yields with broad substrate scope under mild conditions.

Direct β-C(sp3)-H Acetoxylation of Aliphatic Carboxylic Acids

The controlled construction of defined oxidation patterns is one of the key aspects in the synthesis of natural products and bioactive molecules. Towards this goal, we herein report a novel protocol for the Pd-catalyzed direct β-C(sp3)-H acetoxylation of aliphatic carboxylic acids. The protocol enables the use of free carboxylic acids in one step and without the need of introducing specialized strong directing groups. In our studies, we found that the use of a "traceless base" was crucial for the development of a synthetically useful transformation. Furthermore, the synthetic utility of the products obtained was demonstrated by their use in subsequent transformations.

A Catalyst-Free Minisci-Type Reaction: the C–H Alkylation of Quinoxalinones with Sodium Alkylsulfinates and Phenyliodine(III) Dicarboxylates

A direct C–H alkylation of quinoxalinones at the C-3 position with sodium alkylsulfinates and phenyliodine(III) dicarboxylates has been developed under catalyst-free conditions. A series of 3-alkylquinoxalinones were afforded in moderate to excellent yields in this protocol, which offers a practical and efficient access to biologically interesting 3-alkylquinoxalin-2(1H)-one derivatives.

Peptidomimetic synthesis by way of diastereoselective iodoacetoxylation and transannular amidation of 7-9-membered lactams

Azacyclo-and azabicycloalkanone peptidomimetics were synthesized regio-and diastereoselectively by iodoacetoxylation and transannular amidation reactions on unsaturated lactam precursors contingent on ring size olefin position solvent and hypervalent iodi

Preparation method and device for iodobenzene dibenzoate derivative

The invention relates to a preparation method and device for an iodobenzene dibenzoate derivative. The method includes the steps that 6 mmol of iodobenzene diacetate and 12 mmol of benzoic acid or a benzoic acid derivative or pivalic acid are added into a

Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination

In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.

Palladium catalyzed ortho-C-H-benzoxylation of 2-arylpyridines using iodobenzene dibenzoates

A palladium-catalyzed ortho-C-H-benzoxylation of 2-arylpyridines using iodobenzene dibenzoates has been developed. The reaction employed the stable and easily accessible hypervalent iodine reagents as both benzoxylate source and oxidant which made the protocol simple and facile. It showed high regioselectivity and good functional group tolerance, and gave the mono-benzoxylation products in moderate to excellent yields.

Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation

Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.

Catalytic intermolecular amination of C-H bonds: Method development and mechanistic insights

Reaction methodology for intermolecular C-H amination of benzylic and 3° C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3° centers, displays high chemoselectivity for benzylic oxidation, and enables the facile preparation of isotopically enriched 15N-labeled compounds. Access to substituted amines, amino alcohols, and diamines is thereby made possible in a single transformation. Important information relevant to understanding the initial steps in the catalytic cycle, reaction chemoselectivity, the nature of the active oxidant, and pathways for catalyst inactivation has been gained through mechanistic analysis; these studies are also presented.