Article
Chemistry, Organic
Ling Tang, Yangyi Zhang, Guisheng Deng
Summary: In this study, a novel Ag(I)-catalyzed cascade reaction involving enynone cyclization and cross-coupling with phosphorus ylides was achieved for the first time. Subsequent treatment with I-2 led to the formation of corresponding (E)-alpha-alkenylfurans in 73-95% yields with excellent stereoselectivity. A reasonable mechanism has been proposed for the reaction process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jia Seo, Che-Wei Chen, Woohyeong Lee, Ju Eun Jeon, Pei-Ling Chen, Shih-Ching Chuang, Jung Min Joo
Summary: A benzannulation strategy was developed involving activation of two C-H bonds of five-membered heteroarenes, resulting in fluorescent benzofuran and indole derivatives through Pd-catalyzed oxidative reactions. This strategy provides a potential pathway for further development of functionalized polycyclic heteroaromatic compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Stefano Nejrotti, Cristina Prandi
Summary: This review summarizes the advances in the synthesis and functionalization of furans via gold catalysis between 2016 and 2020, focusing on different synthetic methods, functionalization reactions, and tandem reactions.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Toshimichi Ohmura, Yuta Takaoka, Michinori Suginome
Summary: The copper-catalyzed silafunctionalization of alkynes using silylboronic ester as a silicon source has made rapid progress. The trans-selective 1,2-addition of silylboronic esters to internal arylalkynes was efficiently promoted by the CuOt-Bu/RCy2P/NaOt-Bu catalysts, with a stereochemical switch to cis-addition observed in reactions utilizing Me-2(i-PrO)Si-B(pin) in hydrocarbon solvents including cyclohexane.
CHEMICAL COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Aleksandra Blocka, Wojciech Chaladaj
Summary: We report a new method for the synthesis of highly substituted vinylidenecyclopentanes with good yields, complete selectivity, and excellent functional group tolerance. The mechanism involves the oxidative addition of bromoarene to Pd(0), followed by cyclization and reductive elimination. The high regio- and stereoselectivity can be attributed to the 5-exo-dig intramolecular addition of the enol form of the substrate to alkyne activated by the pi-acidic Pd(II) center.
Article
Chemistry, Inorganic & Nuclear
Chuting Zhang, Lijuan Peng, Bohou Song, Zhiwen Li, Xiaoqun Cao
Summary: A sustainable catalyst system for Sonogashira cross-coupling reaction was developed using nanoporous palladium as the catalyst. The catalyst remained stable and active over multiple cycles without significant leaching or loss of activity, and high yields of the desired alkynes were obtained.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yuan Yang, Dilver Pena Fuentes, Xiao-Feng Wu
Summary: Carbonylation reactions are important in contemporary organic chemistry as they provide access to compounds with carbon monoxide or methyl groups. We report a copper-catalyzed carbonylative catenation and borylation reaction and propose a possible reaction mechanism.
Article
Biochemistry & Molecular Biology
Ida Ziccarelli, Lucia Veltri, Tommaso Prestia, Roberta Amuso, Maria A. Chiacchio, Raffaella Mancuso, Bartolo Gabriele
Summary: Unreported 2-(4-acylfuran-2-yl)acetamides were selectively synthesized in fair to good yields (54-81%) over 19 examples through a mild catalytic process involving Csp-H activation, 5-exo-dig O-cyclization, and aromative isomerization.
Article
Chemistry, Applied
Youhei Takeda, Kazuya Toyoda, W. M. C. Sameera, Norimitsu Tohnai, Satoshi Minakata
Summary: A novel palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki-Miyaura arylative cross-coupling has been developed to synthesize enantioenriched 3,3-diarylpropylamines. The mechanism of the reaction was rationalized using density functional theory, with transition states of the selectivity-determining ring-opening step systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Meng Li, Ruixue Zhang, Qiushan Gao, Huanfeng Jiang, Ming Lei, Wanqing Wu
Summary: Herein, a direct and efficient synthesis of diverse polysubstituted fused tetracyclic heterocycles with good functional group tolerance from diarylalkynes under different palladium catalytic systems is presented. The unprecedented intermolecular nucleopalladation of diarylalkynes through the highly selective sequential double insertion of isocyanide was achieved for the first time in this study. The practicality of this method was further demonstrated by the construction of various bioactive molecules and important structural motifs, with potential applications in materials science and biochemistry. In addition, density functional theory calculations revealed an interesting Pd walk during the cyclization process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Lei Xu, Fu-Yue Liu, Qi Zhang, Wei-Jun Chang, Zhong-Lin Liu, Ying Lv, Hai-Zhu Yu, Jun Xu, Jian-Jun Dai, Hua-Jian Xu
Summary: Copper-catalyzed arylboronation is an efficient and versatile carbon-carbon bond formation reaction with potential industrial applications.
Article
Chemistry, Organic
Yi-En Liang, Chih-Yu Kan, Balaji D. Barve, Yen-An Chen, Wen-Tai Li
Summary: A novel Pd-catalyzed reaction was developed for the synthesis of 4H-furo[3,2-c]chromenes and xanthones through tandem cyclization/cross-coupling reaction of 3-alkynyl chromone with aryl iodide. The reaction selectively controlled by KF or a bidentate phosphine ligand exhibited a rare difunctionalization of alkynes through O-attack/5-exo-dig and C-attack/6-endo-dig cyclization. A one-pot tandem process was demonstrated directly from gamma-alkynyl-1,3-diketone for this method.
Article
Chemistry, Organic
Xue-Qiang Chu, Man-Ling Zhi, Si-Xuan Zhang, Ya-Wen Wang, Weidong Rao, Haiyan Xu, Zhi-Liang Shen
Summary: A Pd-catalyzed C-F bond alkynylation of polyfluoroalkyl ketones with terminal alkynes has been developed, providing a series of modular perfluoroalkyl- and alkynyl-substituted furan derivatives with high chemoselectivity and regioselectivity in moderate yields. The success of this cascade reaction relies on the well-controlled sequence of functionalization and alkynylation of multiple C(sp(3))-F bonds. The reaction is presumed to proceed through a chelation-assisted oxidative addition of Pd to the C-F bond based on mechanistic studies.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Evgeniya S. Shutovskaya, Yulia P. Ustimenko, Alexey V. Tkachev, Julia V. Burykina, Alexander M. Agafontsev, Anastasiya V. Lastovka, Dmitriy N. Polovyanenko, Taisiya S. Sukhikh
Summary: In this study, the Pd-catalyzed cross-coupling reaction between α-pinene derivative - pinacarvone O-methyl oxime and aryl halides was described. Surprisingly, the formation of the C-C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The reaction conditions were carefully optimized and the reaction mechanism was proposed based on structural and computational data analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)