Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis
Ravi Varala, Vittal Seema, Narsimhaswamy Dubasi
Organics · pp. 1–40 · Published 23 Dec 2022
10.3390/org4010001Abstract
One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented representative applications of PIDA in organic synthesis involving C-H functionalization, hetero-hetero bond formations, heterocyclic ring construction, rearrangements or migrations and miscellaneous reactions along with their interesting mechanistic aspects starting from the summer of 2015 to the present.
References (40)
- 1 Zhdankin, 2021, Application of hypervalent iodine compounds in advanced green technologies
- 2 Yoshimura, 2016, Advances in synthetic applications of hypervalent iodine compounds [DOI]
- 3 Shetgaonkar, 2021, Hypervalent iodine reagents for oxidative rearrangements
- 4 Zhang, 2020, Hypervalent iodine reagent-mediated reactions involving rearrangement processes [DOI]
- 5 Soni, 2022, Aqueous mediated reactions involving hypervalent iodine reagents [DOI]
- 6 Rani, 2022, Combined approach of hypervalent iodine reagents and transition metals in organic reactions [DOI]
- 7 Kiprof, 2005, The nature of iodine oxygen bonds in hypervalent 10-i-3 iodine compounds
- 8 Wang, 2022, Visible light promoted polyhalomethylation of alkenes: Alkylation and cyclization [DOI]
- 9 Yadav, 2022, Phenyliodine(III) diacetate-mediated dearomatization of 2-(2-hydroxyaryl)benzoxazoles and 2-(2-hydroxyaryl)benzothiazoles: Regio- and stereoselective synthesis of tetramethoxycyclohexenones and bicyclo[2.2.2]octenones [DOI]
- 10 Freitas, 2017, (Diacetoxyiodo)benzene: More than an oxidant [DOI]
- 11 Willgerodt, 1886, Ueber einige aromatische Jodidchloride [DOI]
- 12 Iinuma, 2012, Simple and practical method for preparation of [(diacetoxy)iodo]arenes with iodoarenes and m-chloroperoxybenzoic acid [DOI]
- 13 Hossain, 2005, Alternative, easy preparation of (diacetoxyiodo)arenes from iodoarenes using potassium peroxodisulfate as the oxidant [DOI]
- 14 Togo, 2000, Preparation and reactivities of novel (diacetoxyiodo)arenes bearing heteroaromatics [DOI]
- 15 Xie, 2019, Visible-light-initiated decarboxylative alkylation of quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates in recyclable ruthenium(II) catalytic system [DOI]
- 16 Meyer, 2019, Hydrodifluoromethylation of alkenes with difluoroacetic acid [DOI]
- 17 Zhang, 2022, Switchable, reagent-controlled C(sp3)-H selective iodination and acetoxylation of 8-methylquinolines [DOI]
- 18 Zheng, 2018, (Diacetoxyiodo)benzene-mediated selective synthesis of α-azido ketones or acyl azides from β-keto acids [DOI]
- 19 Opai, 2021, (Diacetoxyiodo)benzene mediated metal-free C(sp2)-H phenylselenation of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles using diphenyl diselenide [DOI]
- 20 Izzo, 2017, A new, practical one-pot synthesis of unprotected sulfonimidamides by transfer of electrophilic NH to sulfinamides [DOI]
- 21 Liu, 2015, Modular preparation of 5-halomethyl-2-oxazolines via PIDA-promoted intramolecular halooxygenation of N-allylcarboxamides [DOI]
- 22 Ma, 2016, Synthesis of quinoxaline derivatives via tandem oxidative azidation/cyclization reaction of N-arylenamines [DOI]
- 23 Schofield, 2021, 5-endo trig oxidative radical cyclizations of Ugi-3CR products toward 1,4-imidazolidinones [DOI]
- 24 Shimizu, 2018, Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents [DOI]
- 25 Zhang, 2015, Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement [DOI]
- 26 Rosa, 2020, A Straightforward Synthesis of N-Substituted Ureas from Primary Amides [DOI]
- 27 Danton, 2019, Phenyliodine(III) diacetate/i2-mediated domino approach for pyrrolo[1,4]thiazines and 1,4-thiazines by a one-pot morin rearrangement of N,S-acetals [DOI]
- 28 Shang, 2018, One-pot synthesis of 2-arylbenzoxazinones from 2-arylindoles with (diacetoxyiodo)benzene as the sole oxidant [DOI]
- 29 Fang, 2020, PhI(OAc)2-promoted 1,2-diaza-cope rearrangement of β,γ-unsaturated Hydrazones with Acetate/H2O: Access to diacyl/acyl N-allylhydrazines [DOI]
- 30 Toth, 2019, Synthesis of multifunctional aryl(trifloxyalkenyl)iodonium triflate salts [DOI]
- 31 Peng, 2022, PIDA-promoted/hfip-controlled dearomative spirocyclization of phenolic ketones via a spirocyclohexadienone-oxocarbenium cation species [DOI]
- 32 Sakamoto, 2018, A Synthetic route to sodium α-aminoalkanesulfinates and their application in the generation of α-aminoalkyl radicals for radical addition reactions [DOI]
- 33 Kalbandhe, 2017, Ring-opening reaction of imidazo[1,2-a]pyridines using (diacetoxyiodo)benzene and NaN3: The synthesis of α-iminonitriles [DOI]
- 34 Kalbandhe, 2016, Oxidative cleavage of c2-c3 bond in isatin using (diacetoxyiodo)benzene: A facile synthesis of carbamates of alkyl anthranilates
- 35 Salvo, 2015, A simple procedure for the oxidation of alcohols using [bis(acetoxy) iodo]benzene and a catalytic amount of bromide ions in ethyl acetate [DOI]
- 36 Al-Matar, H.M., Bin, S., Mohammad, H., and Shalaby, M.A. (2019). Synthesis and electrochemistry of new furylpyrazolino[60]fullerene derivatives by efficient microwave radiation. Molecules, 24. [DOI]
- 37 Li, 2016, Atomic level tuning of the catalytic properties: Doping effects of 25-atom bimetallic nanoclusters on styrene oxidation
- 38 Lin, 2022, Switchable synthesis of 1,4-bridged dihydroisoquinoline-3-ones and isoquinoline-1,3,4-triones through radical oxidation of isoquinolinium salts with phenyliodine(III) diacetate [DOI]
- 39 Yadav, 2022, Phenyliodine(III) diacetate-induced regioselective synthesis of 1-(benzoxazol-2-yl)-1-alkoxynaphthalen-2(1H)- ones from 2-(2-hydroxynaphthyl)benzoxazoles [DOI]
- 40 Tang, 2022, Visible-light-promoted decarboxylative radical cascade cyclization to acylated benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones in water [DOI]
Cited by 78
Akira Yoshimura, Viktor V. Zhdankin · Chemical Reviews · 2024
Pengjie Jiang, Tingting Liu, Chengjun Lei · Journal of the American Chemical Society · 2024
Ravi Varala, Vittal Seema, Mohammed Mujahid Alam · Current Organic Synthesis · 2023
Filip Petko, Magdalena Jankowska, Mariusz Galek · Macromolecules · 2024
Ravi Varala, Vittal Seema, Mohamed Kamel Hussein · ChemistrySelect · 2024
Ravi Varala, Vittal Seema, Mohammed Mujahid Alam · Current Organic Chemistry · 2023
Ravi Varala, Vittal Seema, Mohammed Rizwan Amanullah · Journal of Heterocyclic Chemistry · 2024
Suvam Paul, Sourav Das, Tathagata Choudhuri · Chemistry - An Asian Journal · 2024
Ravi Varala, Kamsali Murali Mohan Achari, Mohamed Hussein · Mini-Reviews in Organic Chemistry · 2025
Ravi Varala, Vittal Seema, Murali Mohan Achari Kamsali · Current Organic Chemistry · 2025
Showing 40 of 78 known citations — external sources report more than can currently be individually listed.
Related research
- A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
- Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
- Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
- Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
- Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage
Article metrics
Real usage data collected on this platform.
0
Page views
0
PDF downloads
0
Outbound clicks
78
Citations
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
No views recorded yet.
Traffic sources
Referring site, by host.
No traffic recorded yet.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.