Review
Chemistry, Applied
Akira Yoshimura, Akio Saito, Viktor V. Zhdankin
Summary: Hypervalent iodine compounds, particularly those based on the benziodoxole heterocyclic system, are widely used as reagents and catalysts in modern organic chemistry. These cyclic hypervalent iodine reagents exhibit higher stability compared to their acyclic analogues, allowing for the safe handling and preparation of reagents with special ligands such as azido, cyano, and trifluoromethyl groups. They have been utilized for the transfer of substituents on hypervalent iodine to organic substrates under various reaction conditions. This review focuses on the recent synthetic applications of cyclic hypervalent iodine(III) reagents with different ligands, including N-3, NHR, CN, CF3, SCF3, OR, OAc, ONO2, and C(=N-2)CO2R, mainly in the past 5 years.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Nagarajan Ramkumar, Larisa Baumane, Dzintars Zacs, Janis Veliks
Summary: A simple process for the oxy-monofluoromethylation of alkenes is presented. The use of visible-light copper(I) photoredox catalysis, in combination with an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands, enables the synthesis of gamma-fluoro-acetates from various olefinic substrates under mild conditions. The study also demonstrates its applications in late-stage diversification of complex molecules, amino acids, and the synthesis of fluoromethylated heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Maxime Denis, Samuel Blais, Sylvain Canesi
Summary: A stereoselective synthesis of isolycoricidine, a natural product belonging to the Amaryllidaceae alkaloids family, was achieved. The study also conducted a synthetic investigation on the main core of lycoricidine, resulting in the formation of analogues and a diastereomer of dihydrolycoricidine. The research utilized various strategies including oxidative phenol dearomatization, stereoselective Heck process, selective dihydroxylation, stereoselective reductions, and oxidative retro-Michael procedure as an amine-deprotecting group strategy. In addition, the study highlighted the usefulness of hypervalent iodines in total synthesis of natural products.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Lachlan Sharp-Bucknall, Tania, Jason L. Dutton
Summary: This article describes the synthesis and structural characterization of NO2-PhI(OTf)(2), a compound that is resistant to decomposition and has higher reactivity than previously misidentified PhI(OTf)(OAc), confirming the non-existence of PhI(OTf)(2) as an intermediate in oxidation reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Maniklal Shee, N. D. Pradeep Singh
Summary: This review investigates the history, structural properties, chemical reactivities and kinetics, methods of generation, and applications of azide radicals in functionalization with unsaturated bonds. The significance of azide radicals in synthesis, drug discovery, biological, and material sciences is highlighted, along with potential opportunities to control their reactivity.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Huaiyuan Zhang, Thomas Wirth
Summary: Xanthene derivatives derived from BINOL have wide applications in various fields such as medicine, fluorescent probes, dyes, and food additives. Researchers have developed synthetic methods for preparing the oxidized products of BINOL using different methods. One-pot reactions of BINOLs, reagents, and nucleophiles have also been investigated, resulting in high-yielding products.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Biochemistry & Molecular Biology
Samata E. Shetgaonkar, Subhiksha Jothish, Toshifumi Dohi, Fateh V. Singh
Summary: The chemistry of hypervalent iodine reagents has become valuable due to their reactivity under mild reaction conditions and resemblance to transition metals. These environmentally friendly reagents are suitable for Green Chemistry. Iodine(V) reagents, such as IBX and DMP, have been used as oxidants in organic synthesis either stoichiometrically or catalytically. This review article describes various oxidation reactions induced by iodine(V) reagents reported in the past decade.
Review
Chemistry, Organic
Irina A. Mironova, Stefan F. Kirsch, Viktor V. Zhdankin, Akira Yoshimura, Mekhman S. Yusubov
Summary: This review summarizes recent approaches to the direct synthesis of organic azides using hypervalent iodine reagents. The first part discusses the use of unstable azidoiodinanes generated in situ, while the second part focuses on the application of stable azidobenziodoxoles as azidating reagents. The use of azidobenziodoxoles allows for selective direct azidation of specific bonds under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Ravi Kumar, Fateh V. Singh, Naoko Takenaga, Toshifumi Dohi
Summary: The review focuses on asymmetric oxidative dearomatization reactions involving hypervalent iodine compounds, summarizing asymmetric intra- and intermolecular dearomatization reactions using chiral hypervalent iodine reagents/catalysts as well as hypervalent iodine-mediated dearomatization reactions followed by desymmetrization.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Correction
Chemistry, Multidisciplinary
Nina Declas, John R. J. Maynard, Laure Menin, Natalia Gasilova, Sebastian Gotze, Jakob L. Sprague, Pierre Stallforth, Stefan Matile, Jerome Waser
Summary: Correction for the paper 'Tyrosine bioconjugation with hypervalent iodine' by Nina Declas et al. presents an improved method for the effective conjugation of tyrosine with hypervalent iodine by rectifying the errors in the original study.
Review
Biochemistry & Molecular Biology
Irina A. Mironova, Dmitrii M. Noskov, Akira Yoshimura, Mekhman S. Yusubov, Viktor V. Zhdankin
Summary: Hypervalent iodine reagents, specifically benziodoxoles, have shown improved thermal stability and synthetic versatility compared to their acyclic analogs. These reagents have found wide applications in direct arylation, alkenylation, and alkynylation reactions under mild conditions, including transition metal-free and photoredox and transition metal catalysis. They enable the synthesis of valuable and structurally diverse complex products through convenient procedures.
Article
Chemistry, Multidisciplinary
Bing Zu, Jie Ke, Yonghong Guo, Chuan He
Summary: Anodic oxidation enables the synthesis and derivatization of hypervalent iodine(III) reagents from aryl iodides under mild electrochemical conditions. This method offers a straightforward and sustainable approach by using only electrons as the oxidation reagents, thus avoiding the use of expensive or hazardous chemical oxidants.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Qi Zhang, Chunlin He, Siping Pang
Summary: A novel synthesis method for heterocyclic fused pyridazine di-N-oxides (triazole, furoxan, furazan) was described. The use of PIDA as a mild oxidant allowed for efficient synthesis of these motifs, solving the issues of harsh conditions and cumbersome manipulation in existing methods. Furthermore, the first synthesis of triazole fused pyridazine di-N-oxide provides a valuable building block for the preparation of biologically relevant molecules and energetic compounds.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Cai Zhang, Jie-Ping Wan
Summary: Diazomethyl-substituted iodine(III) compounds with electron-withdrawing groups have potential reaction abilities and can be used as key intermediates in organic synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Xia Wang, Peng Yang, Bo Hu, Qian Zhang, Dong Li
Summary: A novel transformation of primary amides to secondary amides was developed using hypervalent iodine reagents, promoting a Hofmann-type rearrangement to generate an isocyanate intermediate which was then trapped by a carboxylic acid from the same reagent to provide the corresponding secondary amides. This method not only offers an easy and efficient route for synthesizing secondary amides from primary amides, but also reveals novel reactivities of hypervalent iodine reagents.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Immunology
Angel Josabad Alonso-Castro, Juan Ramon Zapata-Morales, Cesar Solorio-Alvarado, Andrea Hernandez-Santiago, Luis Antonio Espinoza-Ramirez, Candy Carranza-Alvarez, Velayudham Ramadoss
INFLAMMOPHARMACOLOGY
(2020)
Review
Chemistry, Organic
Luis A. Segura-Quezada, Karina R. Torres-Carbajal, Yuvraj Satkar, Kevin A. Juarez Ornelas, Narendra Mali, Dipak B. Patil, Rocio Gamez-Montano, Juan R. Zapata-Morales, Selene Lagunas-Rivera, Rafael Ortiz-Alvarado, Cesar R. Solorio-Alvarado
Summary: Iodine(III)-based reagents are widely used in oxidative reactions for structural functionalization, including fluorination, chlorination, bromination, and iodination protocols. These reagents are applied in oxidative halogenation procedures of arenes, olefins, and alkynes, highlighting the discovery and application of new iodine(III)-based halogenating species.
MINI-REVIEWS IN ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuvraj Satkar, Kazimierz Wrobel, Daniel E. Trujillo-Gonzalez, Rafael Ortiz-Alvarado, J. Oscar C. Jimenez-Halla, Cesar R. Solorio-Alvarado
FRONTIERS IN CHEMISTRY
(2020)
Article
Chemistry, Organic
Josue Valentin-Escalera, Ana Karen Garcia-Duenas, Cesar Rogelio Solorio-Alvarado, Claudia Contreras-Celedon, Carlos Jesus Cortes-Garcia, Luis Chacon-Garcia
Summary: A novel synthetic strategy was developed to obtain 1,6-dihydroazaazulenes derivates through a pseudo-three-component reaction involving cyclization of pyrrolyl-enones. The reaction is efficient, forming three new C-C bonds under mild conditions, and the resulting molecules are considered important in medicinal chemistry.
Article
Endocrinology & Metabolism
Yeniley Ruiz-Noa, Lorena Del Rocio Ibarra-Reynoso, Alan Joel Ruiz-Padilla, Angel Josabad Alonso-Castro, Marco Antonio Ramirez-Morales, Juan Ramon Zapata-Morales, Luis Manuel Orozco-Castellanos, Cesar Rogelio Solorio-Alvardo, Alfredo Lara-Morales
Summary: This study aimed to assess the prevalence of herbal medicine use among patients with type 2 diabetes in central-western Mexico. The results showed a high prevalence of herbal medicine use (59.2%), which was mainly influenced by education level, time of T2DM diagnosis, presence of complications and comorbidities, and insulin usage. Patients with T2DM tend to consume plants like nopal, moringa, and aloe for treatment, especially when experiencing complications or inadequate glycemic control.
PRIMARY CARE DIABETES
(2021)
Article
Plant Sciences
Angel Josabad Alonso-Castro, Victor Arana-Argaez, Eunice Yanez-Barrientos, Julio Cesar Torres-Romero, Rodrigo Javier Chable-Cetz, Katarzyna Worbel, Antonio de Jesus Euan-Canto, Kazimierz Wrobel, Alan Gonzalez-Ibarra, Cesar Rogelio Solorio-Alvarado, Maria del Carmen Juarez-Vazquez
Summary: The study found that Asclepias curassavica has certain anti-inflammatory and analgesic effects without causing sedation or motor coordination impairment. It also demonstrated that the anti-inflammatory activity of ACE is associated with increasing levels of IL-10, while the antinociceptive effect is linked to the involvement of the opioidergic system.
JOURNAL OF ETHNOPHARMACOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Angel Josabad Alonso-Castro, Roberto Serrano-Vega, Salud Perez Gutierrez, Mario Alberto Isiordia-Espinoza, Cesar Rogelio Solorio-Alvarado
Summary: The study found that myristic acid exerts anti-inflammatory effects by increasing IL-10 production in vitro and showed good inhibitory effects on acute and chronic ear edema in vivo. Additionally, its antinociceptive activity is attributed to the involvement of the nitrergic system.
JOURNAL OF FOOD BIOCHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Cesia M. Aguilar-Morales, Jorge Gustavo Araujo-Huitrado, Yamile Lopez-Hernandez, Claudia Contreras-Celedon, Alejandro Islas-Jacome, Angelica Judith Granados-Lopez, Cesar R. Solorio-Alvarado, Jesus Adrian Lopez, Luis Chacon-Garcia, Carlos J. Cortes-Garcia
Summary: This study presents a high-order multicomponent reaction to obtain novel linked 1,5-disubstituted tetrazole-1,2,3-triazole hybrids in low to moderate yield. The cascade process involves Ugi-azide, bimolecular nucleophilic substitution (S(N)2), and copper-catalyzed alkyne-azide reaction (CuAAC), forming six new bonds. The synthesized hybrid compounds show potential as drug candidates for breast cancer treatment, especially those with cyclohexane and halogens in their structures, although further assays are needed to fully understand their effects on cancer cell hallmarks.
Review
Chemistry, Organic
Kotaro Kikushima, Elghareeb E. Elboray, J. Oscar C. Jimenez-Halla, Cesar R. Solorio-Alvarado, Toshifumi Dohi
Summary: This review summarizes the double functionalization of carbon-iodine(iii) and ortho carbon-hydrogen bonds using diaryliodonium(iii) salts, which has significant application value in molecular synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Luis A. Segura-Quezada, Karina R. Torres-Carbajal, Narendra Mali, Dipak B. Patil, Mauricio Luna-Chagolla, Rafael Ortiz-Alvarado, Melissa Tapia-Juarez, Ixamail Fraire-Soto, Jorge Gustavo Araujo-Huitrado, Angelica Judith Granados-Lopez, Rosalinda Gutierrez-Hernandez, Claudia Araceli Reyes-Estrada, Yamile Lopez-Hernandez, Jesus Adrian Lopez, Luis Chacon-Garcia, Cesar R. Solorio-Alvarado
Summary: A gold(I)-catalyzed cycloisomerization procedure was developed for the synthesis of substituted 4H-benzo[d][1,3]-oxazines. The obtained compounds showed potential as drug candidates for breast cancer treatment.
Article
Chemistry, Medicinal
Pradip D. Nahide, Clara Alba-Betancourt, Ruben Chavez-Rivera, Pamela Romo-Rodriguez, Manuel Solis-Hernandez, Luis A. Segura-Quezada, Karina R. Torres-Carbajal, Rocio Gamez-Montano, Martha A. Deveze-Alvarez, Marco A. Ramirez-Morales, Angel J. Alonso-Castro, Juan R. Zapata-Morales, Alan J. Ruiz-Padilla, Claudia L. Mendoza-Macias, Victor Meza-Carmen, Carlos J. Cortes-Garcia, Alma R. Corrales-Escobosa, Rosa E. Nunez-Anita, Rafael Ortiz-Alvarado, Luis Chacon-Garcia, Cesar R. Solorio-Alvarado
Summary: Zygomycetes are widely distributed saprophytic fungi in natural environments that play a role in organic matter transformation. Some zygomycetes of gender Mucor have attracted attention in the health sector due to their ability to infect immunocompromised individuals and the limited pharmacological treatments available for mucormycosis. In this study, a series of 2-aryl-4-aryloxyquinoline-based compounds were found to have fungistatic activity against M. circinelloides, and in some cases, their activity was superior to the reference compound fluconazole. These quinoline derivatives were synthesized using diaryliodonium(III) salts chemistry. A quantitative structure-activity relationship (QSAR) study was conducted to correlate the chemical structure of the compounds with their biological activity. Docking studies were also performed to identify potential targets for the more active quinolines. The results suggested that fluorine- and nitro-containing derivatives exhibited increased activity. This study presents non-described molecules with excellent in vitro activities and potential use in the treatment of mucormycosis.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Elizabeth M. Menuey, John Zhou, Shuyuan Tian, Reid E. Brenner, Zhaoyang Ren, Duy H. Hua, Kathleen Kilway, Shin A. Moteki
Summary: Resin-immobilized catalysts prepared through chirality-driven self-assembly allow for regeneration under mild conditions and quantitative in situ catalyst exchange. The uniqueness of the methodology was demonstrated by preparing a catalyst for TEMPO oxidation and enabling a two-step sequential TEMPO oxidation/aldol condensation sequence with facile catalyst exchange.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Organic
Luis A. Segura-Quezada, Karina R. Torres-Carbajal, Kevin A. Juarez-Ornelas, Angel J. Alonso-Castro, Rafael Ortiz-Alvarado, Toshifumi Dohi, Cesar R. Solorio-Alvarado
Summary: Iodine (III) reagents, with their characteristics of safety, environmental friendliness, and ease of use, have become important alternatives in organic synthesis. They have been widely used in the functionalization of various aromatic cores, introducing multiple functional groups. Furthermore, iodine (III) reagents have significant applications in metal-free arylation reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
John Zhou, Ashley M. Cole, Elizabeth M. Menuey, Kathleen V. Kilway, Shin A. Moteki
Summary: A strategy for building Janus dendrimers via the chirality-directed self-assembly of heteroleptic Zn(ii) BOX complexes is described. This method allows for the quantitative synthesis of Janus dendrimers in situ without the need for purification, with each dendritic domain being recyclable upon disassembly at the focal point.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Claudia Leticia Mendoza-Macias, Cesar Rogelio Solorio-Alvarado, Angel Josabad Alonso-Castro, Clara Alba-Betancourt, Martha Alicia Deveze-Alvarez, Felipe Padilla-Vaca, Arturo Reyes-Gualito
