Article
Chemistry, Organic
Keisuke Mitsugi, Toru Takabayashi, Takayuki Ohyoshi, Hideo Kigoshi
Summary: A strategy for constructing a tricyclo[4.3.1.0(3,7)]decane skeleton, common to many polycyclic polyprenylated acylphloroglucinols, has been established. The total synthesis of nemorosonol was achieved through a tandem Michael addition-intramolecular aldol reaction using 3-ethoxy-1-phenyl-2-proyn-1-one.
Review
Chemistry, Applied
Padinjare Veetil Saranya, Thaipparambil Aneeja, Gopinathan Anilkumar
Summary: The majority of palladium-catalyzed reactions benefit from broad functional group compatibility and gentle reaction conditions. The difluoromethyl group, which possesses fascinating pharmacokinetic properties and is isopolar and isosteric to the hydroxyl group, is present in many agricultural chemicals and drug molecules. Recent efforts to develop new approaches for difluoromethylation and difluoroalkylation reactions have increased notably due to the importance of these compounds in various fields.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chunyu Han, Yuanye Dang, Lin Mo, Ruofei Zhao, Zhengning Wang, Junfeng Zhao
Summary: A straightforward strategy for constructing seven-membered carbocycles through Lewis acid catalyzed intramolecular Michael addition of allenones is reported. It provides an atom-economic access to furan-fused bi- or tricyclic frameworks containing seven-membered carbocycles, which are commonly found in bioactive natural products. Several polycyclic frameworks containing seven-membered carbocycles with diverse functional groups were prepared in good to excellent yields. Furthermore, the strategy was exemplified by the construction of key skeletons of Caribenol A and Frondosin B.
Article
Chemistry, Organic
Kaixuan Song, Min Wen, Kai Shen, Chaogang Fan, Zhenyu Yang, Shaohui Lin, Qinmin Pan
Summary: In this study, an asymmetric version of Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed, achieving excellent asymmetric induction with the use of chiral pyridinooxazoline ligand (S)-t-BuPyOx. Moisture and oxygen-insensitive catalysis was realized under mild conditions, with 9 out of 16 examples giving 92-99% ee.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Wei-Xiang Zheng, Jing Zhong, Yi-Ting Yang, Meluze Luobu, Yan Zhang, Yuan-Hua Wang, Qi-Wei Wang
Summary: Carboxylic acids are commonly used stable reagents in organic synthesis, but their direct use as substrates in the Suzuki-Miyaura coupling reaction is rarely reported. This study presents an efficient coupling reaction between carboxylic acids and arylboronic acids, yielding the corresponding aryl ketones.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Yu-Jie Li, De-Guang Liu, Jin-Hu Ren, Tian-Jun Gong, Yao Fu
Summary: Photocatalytic oxidation is a widely used method in organic synthesis, and has applications in both academia and industry. In this study, we developed a blue light-induced alkylation-oxidation tandem reaction for the synthesis of diverse ketones. This reaction shows excellent functional group compatibility and can be used with a variety of radical precursors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bo Zhou, Shuang Deng, Yin Xu, Xiaotian Qi, Guangbin Dong
Summary: This paper describes the development of a direct functionalization method for carbonyl beta C-H bonds without using directing groups. The reaction enables the beta-alkenylation of ketones with common alkynes through iridium catalysis, and it proceeds under redox neutral conditions, avoiding the need for strong acids or bases, and tolerates various functional groups.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Wenwei Li, Honggui Zhou, Yequan He, Ge Zeng, Yumeng Zheng, Yangni Hu, Zhongyan Chen, Jing-Yuan Ge, Ningning Lv, Jiuxi Chen
Summary: We report a novel pathway to synthesize gamma-lactams using acetonitrile analogues as coupling partners. This method does not require oxidants, ligands, and Lewis acids, and exhibits a broad substrate scope, good functional group tolerance, and excellent chemo/stereoselectivity. Scale-up reactions and late-stage derivatizations demonstrate the potential synthetic utility of this methodology.
Article
Chemistry, Multidisciplinary
Tanmoy Maity, Pameli Ghosh, Soma Das, Debraj Saha, Subratanath Koner
Summary: This study reports the Ullmann C-N coupling reaction of nitroarenes using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions for the first time. The protocol suppresses by-product formation in catalytic reactions, and the catalyst was designed and synthesized through a two-step post-synthesis functionalization process.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Taku Kitanosono, Tomoya Hisada, Yasuhiro Yamashita, Shu Kobayashi
Summary: Metal-bound water molecules have been recognized as a new aspect of soft Lewis acid catalysis. A chiral palladium aqua complex was constructed using a chiral ligand and hydrogen-bond donor, allowing efficient functionalization of carbon-hydrogen bonds of indoles in water. The use of aqueous environments enabled highly enantioselective reactions of sigma-indolylpalladium intermediates, presenting a potentially powerful approach for organometallic transformations under mild conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qian-Qian Ma, Cheng-Jing Li, Wei-Wei Liao
Summary: An efficient method for constructing alpha-amino cyclopentanones with consecutive quaternary and ternary carbon centers is described using an alpha-iminol rearrangement and Pd-catalyzed addition reaction. The method offers high yields, excellent selectivity, and can be used to prepare high-value added compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Stephen Ting, Wendy L. Williams, Abigail G. Doyle
Summary: This study reports the synthesis of a well-defined nickel complex that undergoes oxidative addition with aryl halides, characterized by solution-phase speciation and a redox equilibrium. This has significant implications for organometallic studies of nickel catalysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yoshihiro Shimoyama, Yasutaka Kitagawa, Yuji Ohgomori, Yoshihiro Kon, Dachao Hong
Summary: The hetero-dinuclear Ir-III-Cu-II complex catalyzes the aerobic oxidation of aromatic olefins in water driven by formate, generating Ir-alkyl species and promoting the reaction with Cu-II under acidic conditions. This cooperative catalysis is revealed through spectroscopic detection, kinetic analysis, and theoretical calculations.
Article
Chemistry, Multidisciplinary
Kelu Yan, Min Liu, Jiangwei Wen, Xiao Liu, Xiaoyu Wang, Xinlei Sui, Wenda Shang, Xiu Wang
Summary: The ruthenium-catalyzed aza-Michael addition and intramolecular annulation of enaminones with anthranils to access substituted quinolines has been efficiently realized under simple and easy-to-operate conditions. This method offers an alternative approach for the synthesis of 3-arylformyl substituted quinoline derivatives, with most of the products obtained in good yields.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xun Zhang, Zan Yang, Yu Jiang, Saihu Liao
Summary: Tacticity plays a crucial role in determining the properties of synthetic polymer materials. In this study, a new chiral organic Brønsted acid catalyst was introduced for the cationic polymerization of vinyl ethers, leading to highly stereoselective polymerization reactions. This innovative approach not only produces high-quality isotactic poly(vinyl ethers), but also allows for chain extension to synthesize diblock copolymers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
