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)
Review
Chemistry, Multidisciplinary
Robert R. A. Bolt, Jamie A. Leitch, Andrew C. Jones, William Nicholson, Duncan L. Browne
Summary: This tutorial review discusses the translation from batch-mode ball-milling to flow-mode reactive extrusion using twin-screw extrusion. Mechanochemistry has been established as a powerful approach in sustainable organic synthesis, mainly due to the opportunities offered in solvent-free or highly solvent-minimized reaction systems. However, limitations in scale-up still exist.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Organic
Julian Spils, Thomas Wirth, Boris J. Nachtsheim
Summary: We present a multi-step continuous-flow approach to produce six-membered diaryliodonium salts, with improved scalability and atom economy compared to existing batch methods. Benzyl acetates serve as readily available and cost-effective starting materials in this two-step procedure. An acid-catalyzed Friedel-Crafts alkylation followed by an anodic oxidative cyclization results in a defined set of cyclic iodonium salts, with yield depending on the substrate characteristics.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Arun K. Ghosh, Marc Harper, William L. Robinson
Summary: We present the convergent total syntheses of lycibarbarines A and B, which are recently discovered potent neuroprotective agents derived from Lycium barbarum fruits. The syntheses showcase the construction of a unique spiro oxazine heterocyclic motif found in these natural products. Key starting materials used in the synthesis include commercially available 8-hydroxyquinaline and 2-deoxy-D-ribose, and the synthesis involves Reimer-Tiemann reaction, selective amine alkylation with a keto tosylate derivative, and spiroketalization to form an oxazine core.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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)
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)
Article
Chemistry, Organic
Xiao Xiao, Jessica M. Roth, Nathaniel S. Greenwood, Maria K. Velopolcek, Jordan Aguirre, Mona Jalali, Alireza Ariafard, Sarah E. Wengryniuk
Summary: Bi(N)-HVIs, a newly emerging class of I(V) reagents, demonstrate favorable safety profiles, improved solubility, and comparable to superior oxidative reactivity compared to common I(V) reagents. By incorporating datively bound bidentate nitrogen ligands, these reagents provide a novel and convenient screening platform for the development of I(V) reagents and reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xinhang Zhang, Hanyang Sun, Changhong Han, He Wang, Junpeng Zhang, Di Zhang, Bin Lin, Huiming Hua, Maosheng Cheng, Yongxiang Liu
Summary: The asymmetric total synthesis of neobraclactone C was achieved for the first time using a convergent synthetic strategy, with the longest linear sequence of 22 steps from known materials. Key steps of the synthesis include a steric hindrance/hydrogen bond dual-controlled Heck arylation reaction for the construction of hemiketal and cis-alkenyl in one step, as well as a CeCl3-catalyzed tricycle formation.
Editorial Material
Chemistry, Multidisciplinary
Avijit Roy, Martin Oestreich
Summary: For a long time, the Me3Si group has been difficult to manipulate into another useful functional group, but a hypervalent iodine reagent has now been shown to achieve electrophilic demethylation for this purpose. Coupled with the Tamao-Fleming oxidation, the Me3Si group can serve as a placeholder for a hydroxy group.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
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
Akinobu Kamiya, Yuichiro Kawamoto, Toyoharu Kobayashi, Hisanaka Ito
Summary: The first total synthesis of tricyclic diterpenoid callilongisin B from Callicarpa longissima was achieved through a series of selective reactions, including 1,4-addition, allylation, oxidation, intramolecular aldol reaction, and lactonization. These steps collectively lead to the construction of the target compound's structure.
Article
Chemistry, Multidisciplinary
Hayato Nakagawa, Haruhiko Fuwa
Summary: Stereodivergent synthesis of 2,5-disubstituted pyrrolidines was achieved through a Au-catalyzed tandem intramolecular alkyne hydroamination/iminium formation/Et3SiH reduction. The stereochemical outcome could be switched by selecting an appropriate nitrogen protecting group. Total synthesis of a diastereomeric pair of alkaloid natural products, monomorine I and indolizidine 195B, was successfully accomplished to demonstrate the synthetic utility of the tandem reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Hiroyoshi Takamura, Yuki Sugitani, Ryohei Morishita, Isao Kadota
Summary: The first total synthesis of scabrolide F, a norcembranolide isolated from Sinularia scabra, a soft coral, is described. The key synthetic intermediate, hydroxycarboxylic acid, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was then subjected to macrolactonization and subsequent transannular RCM to obtain scabrolide F. This synthetic protocol can be extended to the total synthesis of other norcembranolides.
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)
