Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols

2019 ◽  
Vol 17 (47) ◽  
pp. 10097-10102 ◽  
Author(s):  
Iveta Klimánková ◽  
Martin Hubálek ◽  
Václav Matoušek ◽  
Petr Beier
Keyword(s):  
Water Soluble ◽  
Hypervalent Iodine ◽  
Group Transfer ◽  
Fluoroalkyl Group

New activated and water-soluble hypervalent iodine reagents were synthesized and used for fluoroalkyl group transfer to cysteine and in reactions with disulfides.

Synthesis and Characterization of Branched Water-Soluble Homopolymers and Diblock Copolymers Using Group Transfer Polymerization

2005 ◽  
Vol 38 (12) ◽  
pp. 4977-4982 ◽  
Author(s):  
V. Bütün ◽  
I. Bannister ◽  
N. C. Billingham ◽  
D. C. Sherrington ◽  
S. P. Armes
Keyword(s):  
Diblock Copolymers ◽  
Water Soluble ◽  
Synthesis And Characterization ◽  
Group Transfer

Organocatalytic Group Transfer Reactions with Hypervalent Iodine­ Reagents

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 359-370 ◽  
Author(s):  
Marcin Kalek ◽  
Manoj Ghosh ◽  
Adam Rajkiewicz
Keyword(s):  
Short Review ◽  
Lewis Base ◽  
Base Catalysis ◽  
Synthetic Methods ◽  
Hypervalent Iodine ◽  
Group Transfer ◽  
Iodine Compounds ◽  
Amine Catalysis ◽  
Brønsted Base ◽  
Brønsted And Lewis Acid

In recent years, a plethora of synthetic methods that employ hypervalent iodine compounds donating an atom or a group of atoms to an acceptor molecule have been developed. Several of these transformations utilize organocatalysis, which complements well the economic and environmental advantages offered by iodine reagents. This short review provides a systematic survey of the organocatalytic approaches that have been used to promote group transfer from hypervalent iodine species. It covers both the reactions in which an organocatalyst is applied to activate the acceptor, as well as those that exploit the organocatalytic activation of the hypervalent iodine reagent itself.1 Introduction2 Organocatalytic Activation of Acceptor2.1 Amine Catalysis via Enamine and Unsaturated Iminium Formation2.2 NHC Catalysis via Acyl Anion Equivalent and Enolate Formation2.3 Chiral Cation Directed Catalysis and Brønsted Base Catalysis via Pairing with Stabilized Enolates3 Organocatalytic Activation of Hypervalent Iodine Reagent3.1 Brønsted and Lewis Acid Catalysis3.2 Lewis Base Catalysis3.3 Radical Reactions with Organic Promoters and Catalysts4 Summary and Outlook

Water-Soluble Hypervalent Iodine(III) Having an I–N Bond. A Reagent for the Synthesis of Indoles

2018 ◽  
Vol 20 (13) ◽  
pp. 4052-4056 ◽  
Author(s):  
Hai-Dong Xia ◽  
Yan-Dong Zhang ◽  
Yan-Hui Wang ◽  
Chi Zhang
Keyword(s):  
Water Soluble ◽  
Hypervalent Iodine

scholarly journals Heterocyclic Group Transfer Reactions with I(III) N-HVI Reagents: Access to N-Alkyl (Heteroaryl)onium Salts via Olefin Aminolactonization

2020 ◽  
Author(s):  
Anthony F. Tierno ◽  
Jennifer C. Walters ◽  
Andres Vazquez-Lopez ◽  
Xiao Xiao ◽  
Sarah Wengryniuk
Keyword(s):  
Hypervalent Iodine ◽  
Alkyl Aryl ◽  
Diversity Oriented Synthesis ◽  
Group Transfer ◽  
Broad Scope ◽  
Nucleophilic Displacement ◽  
Onium Salts ◽  
Recent Emergence ◽  
Iodonium Salt ◽  
Heterocyclic Group

<p>Pyridinium and related N-alkyl (heteroaryl)onium salts are versatile synthetic intermediates in organic chemistry, with applications ranging from ring functionalizations to provide diverse piperidine scaffolds to their recent emergence as radical precursors in deaminative cross couplings. Despite their ever-expanding applications, methods for their synthesis have seen little innovation, continuing to rely on a limited set of decades old transforms. Herein, we leverage (bis)cationic nitrogen-ligated I(III) hypervalent iodine reagents, or <i>N</i>-HVIs, as “heterocyclic group transfer reagents” to provide access to a broad scope of (heteroaryl)onium salts via the aminolactonization of alkenoic acids. The reactions proceed in excellent yields, under mild conditions, and are capable of incorporating a broad scope of sterically and electronically diverse aromatic heterocycles. The <i>N</i>-HVI reagents can be generated <i>in situ</i>, the products isolated via simple trituration, and subsequent derivatizations demonstrate the power of this platform for diversity-oriented synthesis of 6-membered nitrogen heterocycles. Mechanistic studies indicate the reaction proceeds via initial olefin activation followed by lactonization and subsequent intermolecular nucleophilic displacement of an (alkyl)(aryl)iodonium salt hypernucleofuge.</p>

scholarly journals Heterocyclic Group Transfer Reactions with I(III) N-HVI Reagents: Access to N-Alkyl (Heteroaryl)onium Salts via Olefin Aminolactonization

2020 ◽  
Author(s):  
Anthony F. Tierno ◽  
Jennifer C. Walters ◽  
Andres Vazquez-Lopez ◽  
Xiao Xiao ◽  
Sarah Wengryniuk
Keyword(s):  
Hypervalent Iodine ◽  
Alkyl Aryl ◽  
Diversity Oriented Synthesis ◽  
Group Transfer ◽  
Broad Scope ◽  
Nucleophilic Displacement ◽  
Onium Salts ◽  
Recent Emergence ◽  
Iodonium Salt ◽  
Heterocyclic Group

<p>Pyridinium and related N-alkyl (heteroaryl)onium salts are versatile synthetic intermediates in organic chemistry, with applications ranging from ring functionalizations to provide diverse piperidine scaffolds to their recent emergence as radical precursors in deaminative cross couplings. Despite their ever-expanding applications, methods for their synthesis have seen little innovation, continuing to rely on a limited set of decades old transforms. Herein, we leverage (bis)cationic nitrogen-ligated I(III) hypervalent iodine reagents, or <i>N</i>-HVIs, as “heterocyclic group transfer reagents” to provide access to a broad scope of (heteroaryl)onium salts via the aminolactonization of alkenoic acids. The reactions proceed in excellent yields, under mild conditions, and are capable of incorporating a broad scope of sterically and electronically diverse aromatic heterocycles. The <i>N</i>-HVI reagents can be generated <i>in situ</i>, the products isolated via simple trituration, and subsequent derivatizations demonstrate the power of this platform for diversity-oriented synthesis of 6-membered nitrogen heterocycles. Mechanistic studies indicate the reaction proceeds via initial olefin activation followed by lactonization and subsequent intermolecular nucleophilic displacement of an (alkyl)(aryl)iodonium salt hypernucleofuge.</p>

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