Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents

2016 ◽  
Vol 22 (19) ◽  
pp. 6552-6555 ◽  
Author(s):  
Sermadurai Selvakumar ◽  
Ryu Sakamoto ◽  
Keiji Maruoka
Keyword(s):  
Hypervalent Iodine ◽  
Aliphatic Aldehydes

Hypervalent iodine(III) catalyzed radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes under photolysis

Tetrahedron ◽  
2017 ◽  
Vol 73 (40) ◽  
pp. 5841-5846 ◽  
Author(s):  
Sermadurai Selvakumar ◽  
Qi-Kai Kang ◽  
Natarajan Arumugam ◽  
Abdulrahman I. Almansour ◽  
Raju Suresh Kumar ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
Aliphatic Aldehydes

Co-Catalyzed decarbonylative alkylative esterification of styrenes with aliphatic aldehydes and hypervalent iodine(iii) reagents

2019 ◽  
Vol 6 (17) ◽  
pp. 3065-3070 ◽  
Author(s):  
Yong Peng ◽  
Yuan-Yuan Jiang ◽  
Xue-Jiao Du ◽  
Da-You Ma ◽  
Luo Yang
Keyword(s):  
Radical Addition ◽  
Hypervalent Iodine ◽  
Aliphatic Aldehydes ◽  
Alkyl Radicals

Decarbonylation of aliphatic aldehydes into 1°, 2° and 3° alkyl radicals to construct C(sp3)–C(sp3) bond via radical addition and C(sp3)–O bond via the interconversion of CoII–CoIII–CoI.

The radical acylarylation of N-arylacrylamides with aliphatic aldehydes using the photolysis of hypervalent iodine(iii) reagents

2018 ◽  
Vol 16 (30) ◽  
pp. 5412-5415 ◽  
Author(s):  
Ryu Sakamoto ◽  
Naomichi Hirama ◽  
Keiji Maruoka
Keyword(s):  
Uv Light ◽  
Hypervalent Iodine ◽  
Aliphatic Aldehydes

Aradical acylarylation of N-arylacrylamides with aliphatic aldehydes using a combination of hypervalent iodine(iii) reagents and UV light is reported.

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>

Recent Computational Studies on Mechanisms of Hypervalent Iodine(III)-Promoted Dearomatization of Phenols

2020 ◽  
Vol 24 (18) ◽  
pp. 2106-2117
Author(s):  
Hanliang Zheng ◽  
Xiao-Song Xue
Keyword(s):  
Hypervalent Iodine ◽  
Computational Studies ◽  
Mechanistic Studies

Hypervalent iodine-promoted dearomatization of phenols has received intense attention. This mini-review summarizes recent computational mechanistic studies of phenolic dearomatizations promoted by hypervalent iodine(III) reagents or catalysts. The first part of this review describes mechanisms of racemic dearomatization of phenols, paying special attention to the associative and dissociative pathways. The second part focuses on mechanisms and selectivities of diastereo- or enantio-selective dearomatization of phenols.

Enantioselective Alkynylation of Aromatic and Aliphatic Aldehydes Catalyzed by Titanium(IV) Complex of D-Glucosamine-derived Sulfonamides

2014 ◽  
Vol 18 (9) ◽  
pp. 1218-1224 ◽  
Author(s):  
Tomasz Bauer ◽  
Maciej Majdecki ◽  
Slawomir Smolinskia ◽  
Janusz Jurczak
Keyword(s):  
Aliphatic Aldehydes

Formation of Carbon-Oxygen Bond Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions

2020 ◽  
Vol 17 ◽  
Author(s):  
Ayesha Jalil ◽  
Yaxin O Yang ◽  
Zhendong Chen ◽  
Rongxuan Jia ◽  
Tianhao Bi ◽  
...  
Keyword(s):  
Natural Products ◽  
Bond Formation ◽  
Building Blocks ◽  
Review Article ◽  
Hypervalent Iodine ◽  
Metal Free ◽  
Bioactive Natural Products ◽  
The Past ◽  
Oxygen Bond ◽  
Privileged Scaffolds

: Hypervalent iodine reagents are a class of non-metallic oxidants have been widely used in the construction of several sorts of bond formations. This surging interest in hypervalent iodine reagents is essentially due to their very useful oxidizing properties, combined with their benign environmental character and commercial availability from the past few decades ago. Furthermore, these hypervalent iodine reagents have been used in the construction of many significant building blocks and privileged scaffolds of bioactive natural products. The purpose of writing this review article is to explore all the transformations in which carbon-oxygen bond formation occurred by using hypervalent iodine reagents under metal-free conditions

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