Copper‐Catalyzed Electrophilic Amination of Aryl(alkenyl) Boronic Acids with Nitrogen‐containing Hypervalent Iodine (III) Reagent

2021 ◽  
Author(s):  
Weiming Yuan ◽  
Yuanyuan Hu ◽  
Songlin Zheng ◽  
Wu Fan
Keyword(s):  
Boronic Acids ◽  
Hypervalent Iodine ◽  
Electrophilic Amination

Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4303-4308 ◽  
Author(s):  
Dong Li ◽  
Chuancheng Zhang ◽  
Qiang Yue ◽  
Zhen Xiao ◽  
Xianglan Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Electrophilic Amination ◽  
Mild Conditions

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

Electrophilic Amination: An Update

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1525-1535 ◽  
Author(s):  
Zhe Zhou ◽  
László Kürti
Keyword(s):  
Boronic Acids ◽  
Enol Ethers ◽  
Electrophilic Amination ◽  
Silyl Enol Ethers ◽  
Recent Advances

In this account, we provide an overview of some recent advances in electrophilic amination methodologies that have been developed in the Kürti group over the last seven years. Our group’s focus has been to develop novel amination methodologies that directly yield N-unprotected amine products.1 Introduction2 Amination of Boronic Acids3 Aziridination of Unactivated Olefins4 Rhodium-Catalyzed C–H Amination of Arenes5 Synthesis of Carbazoles6 Amination of Aryl- and Alkylmetals7 Doubly Electrophilic N-Linchpin Reagents8 Aza-Rubottom Oxidation of Silyl Enol Ethers9 Summary

scholarly journals One-pot Synthesis of Unsymmetrical Diaryliodonium Tetrafluoroborate Salts Bearing an Isoxazole Moiety from Aryl Boronic Acids

2019 ◽  
Vol 7 (4.14) ◽  
pp. 158
Author(s):  
M A.F. Abdul Manan ◽  
D B. Cordes ◽  
A M.Z. Slawin ◽  
D O’Hagan
Keyword(s):  
Organic Synthesis ◽  
Low Cost ◽  
Boronic Acids ◽  
Environmentally Benign ◽  
Hypervalent Iodine ◽  
Synthetic Method ◽  
One Pot ◽  
Toxic Heavy Metal ◽  
Organometallic Catalysts ◽  
Iodine Compounds

Hypervalent iodine compounds exhibit attractive features of low cost, mild and selective reagents in organic synthesis. These reagents serve as environmentally benign alternatives to toxic heavy-metal based oxidants and expensive organometallic catalysts. The practical and simple synthesis of unsymmetrical diaryl iodonium tetrafluoroborate salts is described. This synthetic method has allowed the production of isoxazole tetrafluoroborate salts from readily available aryl boronic acids without an extra anion exchange step in acceptable yields of 45% and 50%. 

scholarly journals Correction: Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

2016 ◽  
Vol 7 (10) ◽  
pp. 6573-6573
Author(s):  
Guo-Xing Li ◽  
Cristian A. Morales-Rivera ◽  
Yaxin Wang ◽  
Fang Gao ◽  
Gang He ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Hypervalent Iodine

Correction for ‘Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine’ by Guo-Xing Li et al., Chem. Sci., 2016, DOI: 10.1039/c6sc02653b.

scholarly journals Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

2016 ◽  
Vol 7 (10) ◽  
pp. 6407-6412 ◽  
Author(s):  
Guo-Xing Li ◽  
Christian A. Morales-Rivera ◽  
Yaxin Wang ◽  
Fang Gao ◽  
Gang He ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Hypervalent Iodine

A photoredox-mediated Minisci C–H alkylation of N-heteroarenes with easily accessible primary and secondary alkyl boronic acids has been developed.

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

Oxidase Catalysis via an Aerobically Generated Dess-Martin Periodinane Analogue

2018 ◽  
Author(s):  
Asim Maity ◽  
Sung-Min Hyun ◽  
Alan Wortman ◽  
David Powers
Keyword(s):  
Chemical Synthesis ◽  
Aerobic Oxidation ◽  
Substrate Oxidation ◽  
Oxidation Catalysis ◽  
Hypervalent Iodine ◽  
Oxidation Reactions ◽  
Broad Array ◽  
Oxidation Chemistry ◽  
Reactive Oxidants

<p>Hypervalent iodine(V) reagents, such as Dess-Martin periodinane (DMP) and 2-iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to access these reagents from O2 would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. Here, we couple aerobic oxidation of iodobenzenes with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. Further, the developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.</p>

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Electrochemical Vicinal Difluorination of Alkenes: Sustainable, Scalable, and Amenable to Electron-rich Substrates

2019 ◽  
Author(s):  
Sayad Doobary ◽  
Alexi Sedikides ◽  
Henry caldora ◽  
Darren poole ◽  
Alastair Lennox
Keyword(s):  
Bioactive Compounds ◽  
Hypervalent Iodine ◽  
Electrochemical Generation ◽  
Oxidative Decomposition ◽  
Alkyl Groups ◽  
Rich Functionality

Fluorinated alkyl groups are important motifs in bioactive compounds, positively influencing pharmacokinetics, potency and F conformation. The oxidative difluorination of alkenes represents an H important strategy for their preparation, yet current methods are limited in their alkene-types and tolerance of electron-rich, readily oxidized functionalities, as well as in their scalability. Herein, we report a method for the difluorination of a number of unactivated alkene-types that is tolerant of electron-rich functionality, giving products that are otherwise unattainable. Key to success is the electrochemical generation of a hypervalent iodine mediator (in the presence of nucleophilic fluoride and HFIP) using an ‘ex-cell’ approach, which avoids the oxidative decomposition of the substrate. The more sustainable conditions give good to excellent yields of product in up to decagram scales<br>

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