Hypervalent Iodine‐Mediated C3‐Trifluoropropionyloxylation of N‐Substituted Indoles DOI

Yao Tian,

Ming‐Xi Zhou,

Yue Wang

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(37)

Published: Sept. 28, 2024

Abstract A metal‐free hypervalent iodine‐mediated C3‐trifluoropropionyloxylation of N ‐substituted indoles was developed. (Bis‐trifluoropropanoate)iodobenzene used as both the oxidant and fluorine source. The reaction sensitive to ‐protecting groups indoles. ‐acylated provided 3‐trifluoropropionyloxylated indoles, while oxindoles were generated from bearing ‐alkyl groups.

Language: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

Citations

28

tert‐Butyl Hydroperoxide (TBHP): Recent Progress in C−H Functionalization and Heteroatom‐Heteroatom Bond Formations DOI Open Access
Ravi Varala,

Vittal Seema,

Mohamed Hussein

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(30)

Published: Aug. 6, 2024

Abstract tert‐ Butyl hydroperoxide (tBuOOH, TBHP) is a commonly used in many oxidation processes. The primary factors contributing to the increasing usefulness of TBHP include its affordability, eco‐friendliness, exceptional efficacy, and capacity substitute harmful or rare heavy metal oxidants. In this sexennial update, we thoroughly critically examined most noteworthy applications C−H functionalization heteroatom‐heteroatom bond formation reactions from 2018 till present. review has been subdivided based on nature bonds being formed. focuses advantages disadvantages using synthetic organic transformations, as well breadth their use underlying mechanisms involved.

Language: Английский

Citations

4

Role of tert-Butyl Hydroperoxide (TBHP) in Cross-Coupling Reactions DOI Creative Commons
Ravi Varala,

Murali Mohan Achari Kamsali,

Durga Prasad Beda

et al.

IntechOpen eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

tert-Butyl hydroperoxide (tBuOOH, TBHP) is a common used in variety of oxidation processes. The primary reasons for TBHP’s increased usability are its low cost, environmental friendliness, high efficiency, and capacity to replace dangerous or scarce heavy metal oxidants. In this book chapter, we have reviewed briefed up representative applications TBHP cross-coupling reactions from 2014 the present.

Language: Английский

Citations

0

Iodoxybenzoic Acid (IBX) in Organic Synthesis: A Septennial Review DOI
Ravi Varala, Vittal Seema, Mohammed Mujahid Alam

et al.

Current Organic Synthesis, Journal Year: 2023, Volume and Issue: 21(5), P. 607 - 664

Published: Oct. 19, 2023

This study reviews the oxidative applications of 2-iodoxybenzoic acid (IBX) in organic synthesis, focusing on C-H functionalization, hetero-hetero bond formations, ring cleavage reactions, dehydrogenation, heterocyclic and some miscellaneous reactions a comprehensive critical way. It compiles literature starting from mid-2015 to date.

Language: Английский

Citations

9

Recent Advances in Hypervalent Iodine Reagents and m-CPBA Mediated Oxidative Transformations DOI
Ravi Varala, Vittal Seema, Mohammed Amanullah

et al.

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(7), P. 489 - 509

Published: March 14, 2024

Abstract: Among the several peroxides available, meta-chloroperbenzoic acid (mCPBA) plays an efficient role of oxidizing reagent and is used for many oxidative transformations, such as oxidation various functional groups, carbon-carbon, carbon-hetero bond formation, heterocyclic ring heteroarylation, cross-coupling, lactonization, dearomatization, α-oxytosylation or α-acetoxylation, C-C activation in other miscellaneous reactions. The purpose this review to critically discuss significant contributions mCPBA along with hypervalent iodine/iodine reagents organic synthesis from mid-2015 date.

Language: Английский

Citations

3

Dess-Martin Periodinane (DMP) in Organic Synthesis-A Septennial Update (2015-till Date) DOI
Ravi Varala, Vittal Seema, Mohammed Mujahid Alam

et al.

Current Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(17), P. 1504 - 1530

Published: Sept. 1, 2023

Abstract: Dess-Martin periodinane (DMP) is one of the hypervalent iodines that most frequently utilized as an oxidizing agent in organic chemistry. The authors this septennial review have critically and methodically presented representative applications DMP synthesis from 2015 to present, including oxidations, dehydrogenations, hetero homo-dimerizations, aromatizations, thiocyanations, halogenations, dearylations, ring expansions, cyclizations, heterocyclic formation, other miscellaneous reactions. This discusses range constraints these transformations.

Language: Английский

Citations

7

Recent advances in TBHP‐promoted heterocyclic ring construction via annulation/cyclization DOI
Ravi Varala,

Vittal Seema,

Mohammed Amanullah

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: 61(8), P. 1269 - 1298

Published: June 2, 2024

Abstract One of the most often utilized hydroperoxides in an array oxidation strategies is tert ‐butyl hydroperoxide ( t BuOOH, TBHP). The key reasons for rising utility TBHP are its low cost, environmental friendliness, high efficiency, and ability to replace hazardous or rare heavy metal oxidants. In this sexennial update, we concisely critically discussed applications heterocyclic ring formations starting from 2018 date. Merits demerits utility, scope a synthetic organic transformation along with mechanistic logistics features review.

Language: Английский

Citations

2

Easy Access to α-Ketothioamides via Oxidative Amidation of Bunte Salts Using Electrolysis or Hypervalent Iodine DOI

Neha Sharma Prabhakar,

Kaushal Kishor,

Krishna Nand Singh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13329 - 13337

Published: Sept. 10, 2024

Two new protocols leveraging electrochemical and hypervalent iodine-mediated synthesis of α-ketothioamides have been developed by using easily accessible cost-effective Bunte salts secondary amines. The methods are efficient, simple, straightforward, showcase the formation C-N bonds across diverse substrates under ambient conditions.

Language: Английский

Citations

2

Recent advances in metal-mediated oxidations with mCPBA DOI
Ravi Varala, Surbhi Dhadda,

Vittal Seema

et al.

Transition Metal Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: June 24, 2024

Language: Английский

Citations

1

PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes DOI

Suvam Paul,

Sourav Das,

Tathagata Choudhuri

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 4, 2024

We have developed a visible-light-mediated convenient and efficient strategy for the iodination of heteroarenes using diacetoxyiodobenzene (PIDA) under photocatalyst-free conditions. This unique approach is first report on photocatalytic C-H employing PIDA as iodinating agent. The new applicable to wide range pyrazolo[1,5-a]pyrimidine derivatives with various functionalities. Iodination other electron-rich heterocycles like imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, pyrazoles has been accomplished this benign protocol. usefulness 3-iodo synthetic intermediate in synthesizing functionalized pyrazolo[1,5-a]pyrimidines demonstrated.

Language: Английский

Citations

1