Article
Chemistry, Multidisciplinary
Kezhuo Zhang, Chenchen Li, Yining Jia, Wanxiang Zhao
Summary: This study presents a novel strategy for the preparation of gamma-lactones through the oxidation of enynyl boronates. By oxidizing the C(sp)-B bond and subsequently performing epoxidation and lactonization, various gamma-lactones and unsaturated butenolides can be efficiently synthesized. Furthermore, asymmetric oxidative lactonization of enynyl boronates can generate chiral gamma-lactones with high enantioselectivities and diastereoselectivities. The versatile transformations and prevalence of gamma-lactones highlight the importance of this strategy in the construction and late-stage functionalization of complex molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Feilong Sun, Chengxi Yang, Jie Ni, Gui-Juan Cheng, Xianjie Fang
Summary: A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported, where appropriate ligands result in high yields and regioselectivities of two different enynyl nitriles. DFT calculations show that different ligands lead to diverse alkyne insertion modes, impacting the regioselectivity. The synthetic value of cyano-containing 1,3-enynes is demonstrated through downstream transformations.
Article
Chemistry, Organic
Ivan A. Yaremenko, Yulia Yu. Belyakova, Peter S. Radulov, Michael G. Medvedev, Nikolai V. Krivoshchapov, Igor V. Alabugin, Alexander O. Terent'ev
Summary: The relief of stereoelectronic frustration drives the acid-catalyzed three-component condensation, allowing the preparation of otherwise inaccessible compounds rapidly and selectively.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ariel L. Burgio, Nicklas W. Buchbinder, Webster L. Santos
Summary: A facile method for the synthesis of (Z)-1,3-enynes is achieved through sequential copper-catalyzed regio- and stereoselective borylation-protodeboronation of 1,3-diynes. Pinacolborane, copper(II) acetate, and Xantphos are utilized as the ligand to efficiently introduce hydrogen and Bpin in a cis fashion, followed by rapid hydrolysis with water. The reaction exhibits wide substrate scope and proceeds in a chemoselective manner.
Article
Chemistry, Multidisciplinary
Undamatla Suri Babu, Ramesh Kotipalli, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: Reaching the formidable C-H corners has been a major challenge in organic chemistry, and this study presents a novel approach using 2-iodo benzoates, indoles, and carbazoles with N-embedded 1,6-enynes through 7-/8-membered palladacycles. This method allows the formation of multicyclic scaffolds without the assistance of any directing group, and the resulting products can be easily diversified with new functional groups and/or three contiguous stereocenters, including a rare benzylic mono-oxygenation reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Pharmacology & Pharmacy
Alen Gabric, Ziga Hodnik, Stane Pajk
Summary: Oxidation is a common degradation pathway for pharmaceuticals, and it is more complex than hydrolysis, producing a wide range of degradation products. Accelerated studies of drug-excipient mixtures can provide realistic insights into degradation in the solid state, as excipients are the main sources of impurities that can initiate oxidation. Based on the results of these studies, appropriate measures can be taken to minimize the oxidation of solid drug products.
Article
Chemistry, Organic
Shi-Yin Tian, Jing-Jing Ai, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: A photocatalytic synthesis method was developed to simultaneously construct two C-S/Se bonds and one C-C bond without the use of transition metals or other additives, using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shivam A. A. Meena, Poonam Sharma, Akhilesh K. K. Verma
Summary: A transition-metal-free one-pot synthesis of di-functionalized succinimides has been developed, which involves a radical cascade seleno/thiosulfonation of aza-1,6-enynes in an atom economical manner. This method allows the synthesis of highly decorated succinimides with excellent stereoselectivity under mild reaction conditions. The proposed radical pathway is well supported by control experiments. The reaction demonstrates advantageous features including operational simplicity, atom economy, and broad substrate scope.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Mengning Wang, Qiuzhu Wang, Mengtao Ma, Binlin Zhao
Summary: A copper-catalysed synthesis of trifluoromethyl allenes has been developed, providing a simple and practical platform for the preparation of substituted allenes with a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Engineering, Environmental
Xianhu Long, Hongle Shi, Rongfu Huang, Lingyun Gu, Yang Liu, Chuan-shu He, Ye Du, Zhaokun Xiong, Wen Liu, Bo Lai
Summary: In this study, sustainable Fe(III)/Fe(II) cycles in different inorganic peroxides activation systems were accelerated by using electro-catalysis (EC) as the electron donor. The electro-cocatalytic Fenton-like systems exhibited excellent degradation efficiency of sulfamethoxazole (SMX). Various reactive oxygen species (ROS) including hydroxyl radical ((OH)-O-center dot), singlet oxygen (O-1(2)), and sulfate radical (SO4 center dot-) were produced in EC/Fe(III)/PMS system, contributing to 38%, 37%, and 24% respectively. The dominant ROS in EC/Fe(III)/ PDS and EC/Fe(III)/HP processes was (OH)-O-center dot. The study provides a strong basis for constructing suitable systems to achieve different treatment requirements.
JOURNAL OF HAZARDOUS MATERIALS
(2023)
Article
Chemistry, Organic
Leah Kuhn, Vera A. Vil, Yana A. Barsegyan, Alexander O. Terent'ev, Igor V. Alabugin
Summary: We demonstrate that the carboxylate radical can coordinate with certain high-spin transition metal centers as an L-ligand. This coordination maintains the O-radical character required for C-H activation through hydrogen atom transfer. The capture of the new C-radical by the metal and subsequent reductive elimination leads to formal C-H acyloxylation. Decarboxylation of the RCO2 radical is minimized due to the hybridization effects introduced by the spiro-cyclopropyl moiety.
Article
Chemistry, Multidisciplinary
Nataliya N. Makhmudiyarova, Irina R. Ishmukhametova, Kamil R. Shangaraev, Lilya U. Dzhemileva, Vladimir A. D'yakonov, Askhat G. Ibragimov, Usein M. Dzhemilev
Summary: An efficient method for synthesizing benzannelated macrocyclic di- and triperoxides has been developed, and it has been demonstrated for the first time using flow cytometry that these compounds are efficient apoptosis inducers in tumor cell cultures and fibroblasts.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Yury A. Vasev, Ekaterina R. Nasibullina, Anton S. Makarov, Maxim G. Uchuskin
Summary: The key carbenoid intermediate in the transition-metal-catalyzed furan-yne cyclization of Hashmi phenol synthesis can be efficiently reacted with water under improved reaction conditions to provide functionalized unsaturated dicarbonyl compounds, which can serve as convenient precursors for the straightforward synthesis of annulated pyridazines.
Article
Chemistry, Multidisciplinary
Dong Xia, Liu-Yu Shen, Yicheng Zhang, Wen-Chao Yang
Summary: In this work, we report on a new N-centered radical initiated spirocyclization of biaryl ynones under metal- and additive-free conditions. This approach features good functional group tolerance and provides a facile and green way for the construction of NO2-containing spiro[5.5]trienones.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Shaoqun Zhu, Yuejie Sun, Yingjie Pan, Xiaoyun Chen, Huaguang Yu, Ying Han, Chaoguo Yan, Yaocheng Shi, Hong Hou
Summary: In this study, a novel hydroalkylative cyclization method was developed using visible-light photoredox catalysis, resulting in the synthesis of various alkenyl heterocyclic compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
