Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups

Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups

The reactivity of benzyl hypervalent iodine intermediates was explored in congruence with the reductive iodonio-Claisen rearrangement (RICR) to show that there may be an underlying mechanism which expands the reasoning behind the previously known C–C bond-forming reaction. By rationalizing the hyper...

Full description

Bibliographic Details
Main Authors:	Cyrus Mowdawalla, Faiz Ahmed, Tian Li, Kiet Pham, Loma Dave, Grace Kim, I. F. Dempsey Hyatt
Format:	Article
Language:	English
Published:	Beilstein-Institut 2018-05-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	electrophilic aromatic substitution hypernucleofugality hypervalent iodine iodonio-Claisen transmetallation
Online Access:	https://doi.org/10.3762/bjoc.14.91

Similar Items

Recent Advances in Electrophilic CF3-Transfer Using Hypervalent Iodine(III) Reagents
by: Iris Kieltsch, et al.
Published: (2008-04-01)

Hypervalent Iodine-based Trifluoromethylating Agents Made in Switzerland
by: Nico Santschi, et al.
Published: (2014-06-01)

Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine
by: Jianlin Han, et al.
Published: (2020-04-01)

Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers
by: Kensuke Kiyokawa, et al.
Published: (2018-05-01)

Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
by: Kazuhiro Watanabe, et al.
Published: (2019-03-01)

Regio- and stereoselective access to highly substituted vinylphosphine oxides via metal-free electrophilic phosphonoiodination of alkynes
by: Dong, Bingbing, et al.
Published: (2024)

Halogen bonding in hypervalent iodine and bromine derivatives: halonium salts
by: Gabriella Cavallo, et al.
Published: (2017-07-01)

Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
by: Mio Shimogaki, et al.
Published: (2015-09-01)

Thiolate photocatalysis enables radical borylation of reductively inert aryl electrophiles
by: Li, Haoyu, et al.
Published: (2022)

Iodoarylation of Arylalkynes with Molecular Iodine in the Presence of Hypervalent Iodine Reagents
by: Md. Ataur Rahman, et al.
Published: (2009-08-01)

Determining the predominant tautomeric structure of iodine-based group-transfer reagents by 17O NMR spectroscopy
by: Nico Santschi, et al.
Published: (2018-08-01)

α-Lithiation and Electrophilic Substitution of 1,4,4-Trimethyl-3,4-dihydroquinolin-2-one
by: Bouclé Sébastien, et al.
Published: (2010-10-01)

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes
by: Xiang Li, et al.
Published: (2018-07-01)

Chiral 2-Aminobenzimidazole as Bifunctional Catalyst in the Asymmetric Electrophilic Amination of Unprotected 3-Substituted Oxindoles
by: Llorenç Benavent, et al.
Published: (2018-06-01)

Editorial: New Hypervalent Iodine Reagents for Oxidative Coupling
by: Toshifumi Dohi, et al.
Published: (2021-02-01)

Chiral Hypervalent, Pentacoordinated Phosphoranes
by: Dorota Krasowska, et al.
Published: (2016-11-01)

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent
by: Elsa Deruer, et al.
Published: (2018-05-01)

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents
by: Samata E. Shetgaonkar, et al.
Published: (2022-06-01)

A survey of chiral hypervalent iodine reagents in asymmetric synthesis
by: Soumen Ghosh, et al.
Published: (2018-05-01)

Synthesis of Uracil-Iodonium(III) Salts for Practical Utilization as Nucleobase Synthetic Modules
by: Naoko Takenaga, et al.
Published: (2019-08-01)

Cyclopropanes and Hypervalent Iodine Reagents: High Energy Compounds for Applications in Synthesis and Catalysis
by: Davinia Fernández González, et al.
Published: (2011-09-01)

Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer
by: Renzo Luisi, et al.
Published: (2023-01-01)

Editorial: New hypervalent iodine reagents for oxidative coupling—volume II
by: Toshifumi Dohi, et al.
Published: (2022-09-01)

Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions
by: Samata E. Shetgaonkar, et al.
Published: (2020-09-01)

Synthesis and Electrophilic Substitution of Pyrido[2,3,4-kl]-acridines
by: Yoel Kashman, et al.
Published: (2001-03-01)

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds
by: Marta Papis, et al.
Published: (2023-08-01)

Atom-economical group-transfer reactions with hypervalent iodine compounds
by: Andreas Boelke, et al.
Published: (2018-05-01)

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents
by: Fateh V. Singh, et al.
Published: (2018-07-01)

Nitração aromática: substituição eletrofílica ou reação com transferência de elétrons? Aromatic nitration: electrophilic substitution or reaction with electron transfer?
by: Sheila Pressentin Cardoso, et al.
Published: (2001-06-01)

Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides
by: Eman Zawia, et al.
Published: (2016-08-01)

The Tetrel Bonds of Hypervalent Halogen Compounds
by: Zhihao Niu, et al.
Published: (2023-10-01)

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle
by: Akira Yoshimura, et al.
Published: (2018-05-01)

Electrophile Modulation of Inflammation: A Two-Hit Approach
by: James O’Brien, et al.
Published: (2020-11-01)

ELECTROPHILIC CYCLIZATION OF DITERPENOIDS
by: Veaceslav Kulciţki, et al.
Published: (2006-06-01)

Synthesis and Properties of <i>ortho</i>-<i>t</i>-BuSO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>-Substituted Iodonium Ylides
by: Tomohiro Kimura, et al.
Published: (2021-09-01)

Hypervalent IodineÃ¢Â€Â“Mediated Ring Contraction Reactions
by: Luiz F. Silva
Published: (2006-06-01)

Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against <i>T. b. rhodesiense</i> and <i>P. falciparum</i> Strain NF54
by: Nina Scheiber, et al.
Published: (2022-10-01)

Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents
by: Samata E. Shetgaonkar, et al.
Published: (2022-07-01)

Mechanism-Dependent Selectivity: Fluorocyclization of Unsaturated Carboxylic Acids or Alcohols by Hypervalent Iodine
by: Jiaqi Su, et al.
Published: (2022-05-01)

Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)
by: Morifumi Fujita, et al.
Published: (2018-03-01)