Article
Chemistry, Organic
Dong-Ting Dai, Meng-Wei Yang, Zhi-Yuan Chen, Zi-Lu Wang, Yun-He Xu
Summary: An efficient palladium-catalyzed asymmetric synthesis of axially chiral conjugated dienes via alkenyl C-H olefination is reported. The corresponding atropisomeric styrenes were obtained with good yields and enantioselectivities. This synthetic strategy offers easy operation, mild reaction conditions, wide functionality tolerance, and high efficiency.
Article
Chemistry, Organic
Yan Xu, Tong Su, Jie-Rui Zhang, Hua-Jiao Ding, Yuanji Gao, Minghui Xu, Peng Cao, Ping Hu, Bi-Qin Wang, Bin Chen
Summary: A regio- and stereoselective nickel-catalyzed reductive three-component cross-coupling reaction between 1,3-butadiene, aldehydes, and alkenyl triflates or bromides was developed. This method provides a convenient access to the synthesis of skipped diene compounds bearing various functional groups and heterocyclic moieties. The utility of this reaction was demonstrated by scale-up preparation and diverse transformations.
Review
Biochemistry & Molecular Biology
Shaheera Tabassum, Ameer Fawad Zahoor, Sajjad Ahmad, Razia Noreen, Samreen Gul Khan, Hamad Ahmad
Summary: Cross-coupling reactions are powerful tools for synthesizing natural products, with Suzuki, Negishi, Heck, Sonogashira, and Stille reactions being commonly used in total synthesis. This review highlights the significance of these reactions in organic synthesis and provides examples of incorporating multiple types of cross-coupling reactions in the synthesis of natural products.
MOLECULAR DIVERSITY
(2022)
Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xinyi Li, Long Liu, Tianzeng Huang, Zhi Tang, Chunya Li, Wenhui Li, Tao Zhang, Zhaohui Li, Tieqiao Chen
Summary: A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis without the use of excess oxidants, providing a relatively general method for preparing internal alkynes.
Article
Chemistry, Physical
C. Rose Kennedy, Matthew Joannou, Janelle E. Steves, Jordan M. Hoyt, Carli B. Kovel, Paul J. Chirik
Summary: This study describes the selective intermolecular homodimerization and cross-cycloaddition of vinylsilanes with unbiased 1,3-dienes catalyzed by a pyridine-2,6-diimine (PDI) iron complex. The chemoselectivity of these reactions was found to be distinct from that of similar alpha-olefin reactions with 1,3-dienes. Mechanistic studies provided insights into substrate-controlled regioselectivity, and identified diamagnetic iron diene and paramagnetic iron olefin complexes as catalyst resting states. The relative rates of beta-H elimination and C-C reductive elimination were ultimately governed by the silyl substituents, dictating final product formation.
Article
Chemistry, Multidisciplinary
Quentin Ronzon, Wei Zhang, Thomas Charote, Nicolas Casaretto, Gilles Frison, Bastien Nay
Summary: This study describes the total synthesis of two fungal cyclotripeptides, (+)-cinereain and (-)-janoxepin, which possess a complex heterocyclic core and exhibit interesting phytotoxic and antimalarial activities. The key step in the synthesis is a one-pot cascade reaction that releases a reactive spiro[2-vinylcyclopropane-1,5'-pyrimidine-4',6'-dione] intermediate through the cyclocondensation of two fragments. This intermediate undergoes a spontaneous retro-Claisen rearrangement, leading to the formation of a 2,5-dihydrooxepin-fused heterocyclic product. The challenging oxepin ring is finally forged through a palladium-catalyzed beta-hydride elimination of an allylic fluoride intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ya-Qiong Qi, Shuai Liu, Yan Xu, Yang Li, Tong Su, Hai-Liang Ni, Yuanji Gao, Wenhao Yu, Peng Cao, Ping Hu, Ke-Qing Zhao, Bi-Qin Wang, Bin Chen
Summary: We report an efficient Ni-catalyzed three-component cross-electrophile coupling reaction, which accomplishes dicarbofunctionalization of 1,3-dienes by forming two new C-C bonds in one reaction.
Article
Chemistry, Multidisciplinary
Haibo Wu, Zhiyao Zheng, Kaiheng Zhang, Johan Kajanus, Magnus J. Johansson, Armando Cordova, Jan-E. Baeckvall
Summary: A sustainable methodology for the synthesis of chiral allenes was reported using a simple and cheap cellulose supported heterogeneous nanocopper catalyst. High yields and excellent enantiospecificity were achieved for diverse 1,3-di and tri-substituted allenes, and the recycling of the catalyst was also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Pablo Chourreu, Olivier Guerret, Loic Guillonneau, Eric Gayon, Guillaume Lefevre
Summary: A convenient procedure for iron-catalyzed cross-coupling of alkyl or aryl Grignard reagents and conjugated dienyl bromides has been reported. The use of cheap and non-toxic magnesium alkoxides as sole additives led to excellent stereoselectivity in the alkyl-dienyl series. Preliminary mechanistic studies suggest in situ generated ate homoleptic organoiron(II) species act as catalytically relevant intermediates.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Takahide Fukuyama, Baptiste Picard, Ilhyong Ryu
Summary: This paper summarizes our team's efforts over the past two decades in the development of new catalytic methods for C-C bond formation. The versatile applications of the commercially available catalyst RuHCl(CO)(PPh3)(3) (or RuH for short) are highlighted through eight different transformations. The fundamental steps involved in the catalysis are emphasized, demonstrating how our mechanistic understanding and the diverse catalytic capabilities of RuH can be utilized to design desired catalytic cycles and develop new cross-coupling reactions with high atom-economy.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Soojun Park, Jiwoo Lee, Jae Hyun Kim, Yeji Jeong, Seokwoo Lee, Su Won Lee, Sanghee Kim
Summary: A concise total synthesis of salinosporamides and cinnabaramides was achieved through the combined use of memory of chirality and dynamic kinetic resolution principles, involving aldol reactions and hydrolysis reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Biping Xu, Weiping Su
Summary: In this paper, we report a transition metal-free, operationally simple, general method for the straightforward synthesis of 2-substituted benzoxazoles from readily available cyclohexanones and aliphatic primary amines. The key to the success of this method is the use of TEMPO as a mild oxidant, which selectively oxidizes the reaction intermediates through its multiple reactivity modes, allowing the individual steps to proceed in succession. This protocol demonstrates high reliability and excellent functional-group tolerance, enabling the synthesis of structurally diverse products, including marketed drugs, drug candidates, and natural products that are unattainable by existing methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Mohamad Estaitie, Dennis G. Hall
Summary: The palladium-catalyzed cross-coupling reaction of optically enriched dehydropiperidinyl boronate with cinnamyl carbonates was optimized to minimize stereochemical erosion, providing exclusively linear 2-allylated 3,4-dehydropiperidines with high enantiospecificity using (p-CF3C6H4)(3)P as the ligand.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Bijan Mirabi, Austin D. Marchese, Mark Lautens
Summary: In this study, a nickel-catalyzed cross-electrophile coupling reaction of aryl chlorides and heteroaryl chlorides was reported, enabled by a synergistic combination of halide effects and the addition of a magnesium salt. Electronic-deficient aryl chlorides were found to perform the best in the reaction, and preliminary mechanistic evidence showed that MgCl2 is crucial for accelerating the reduction of Ni(II) while small quantities of iodide lead to improved yields.
