Article
Chemistry, Physical
Jian-Shu Wang, Jiangjie Zhang, Siqi Wang, Jun Ying, Chuan-Ying Li, Xiao-Feng Wu
Summary: A novel palladium-catalyzed domino carbonylative cyclization has been developed for the rapid construction of functionalized heterocycles. The reaction proceeds smoothly with the consecutive formation of C-C and C-X bonds using benzene-1,3,5-triyl triformate as the CO source, yielding a variety of biologically relevant derivatives.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Shubham Dutta, Akhila K. K. Sahoo
Summary: This paper describes a Pd-catalyzed three-component syn-1,2-arylmethylation method, which successfully synthesizes methyl-containing tetra-substituted olefins by using readily available and stable coupling partners iodo-arenes and methyl boronic acid. The reaction shows a broad scope with excellent functional-group tolerance and exhibits remarkable regio- and stereoselectivity. Biologically relevant motifs (BRM) bearing iodo-arenes and ynamides are also used for late-stage syn-1,2-arylmethylation of alkynes. Additionally, aryl-alkylation, aryl-trideuteriomethylation, alkynyl-methylation, and alkenyl-methylation of ynamides are presented, leading to the synthesis of synthetically important beta-amino-indenones and alpha-fluoro-alpha '-methyl ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shangbiao Zhang, Yan Gao, Rui Xiao, Yang Li, Yanan Wang, Zheliang Yuan
Summary: In this study, a tandem synthesis of various CF3Se-containing heterocyclic compounds was developed using Tf2O as the catalyst and trifluoromethyl selenoxides as the electrophilic trifluoromethylselenolation reagents. The process is characterized by its mild conditions, easy operation, and good functional group compatibility. A variety of alkynes were successfully transformed into CF3Se-containing indoles, benzofurans, benzothiophenes, isoquinolines, and chromenes in good yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Subhankar Ghosh, Shital K. Chattopadhyay
Summary: In this study, a single metal catalyst and air as the oxidant were used to achieve tandem C-H arylation and C-H amidation of cis-cinnamyl hydroxamates, leading to the regioselective formation of a 3-aryl-2-quinolone ring system. Under identical conditions, the corresponding trans-isomer resulted in a 4-aryl-2-quinolone derivative. The observed complementary regioselectivity during the tandem C-H arylation and C-H amidation of isomeric substrates is unusual and has potential applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Hayeon Kwak, Eunsu Kang, Jae Yeong Song, Geunhee Kang, Jung Min Joo
Summary: The development of modular approaches for heteroaromatic cores and substituents is crucial for drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The Pd catalytic system transformed a variety of five-membered heteroarenes to the corresponding benzofused products, demonstrating its versatility in the annulation of (hetero)aromatic rings.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Marina Yu. Dvorko, Dmitrii A. Shabalin, Igor A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov
Summary: The cascade dimerization of alkynones with sterically hindered secondary alkyl groups at the carbonyl function unexpectedly produced highly functionalized furans. This reaction efficiently takes place at room temperature in the presence of a potassium tert-butoxide/dimethylsulfoxide superbase catalytic system. Alkynones with an additional C-H active site at the carbon-carbon triple bond followed a different dimerization pathway to form 3-alkenylpyran-4-ones. The discovery of these reactions expands the traditional understanding of alkynone reactivity in strong basic conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jasper L. Tyler, Adam Noble, Varinder K. Aggarwal
Summary: This study reports a multicomponent reaction method for the synthesis of diverse compound libraries based on azetidine rings. The method allows for rapid reactions and high variability, and has been demonstrated in the synthesis of the EP2 receptor antagonist PF-04418948.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Xavier Abel-Snape, Gina Wycich, Mark Lautens
Summary: A palladium-catalyzed three-component domino reaction for accessing indene derivatives is described. The reaction involves the sequential formation of three bonds, with the first two resulting from inter- and intramolecular carbopalladation, and the final bond arising from an attack by a terminating nucleophilic reagent. The starting tether on the iodoarene can be modified to yield either indenes or benzofulvenes. Additionally, the use of an oxabicycle as an acetylene surrogate is demonstrated, and the enantioselective synthesis of indenes is preliminarily explored.
Article
Chemistry, Multidisciplinary
Ru-Yu Hua, Si-Fan Yu, Xiao-Ting Jie, Huang Qiu, Wen-Hao Hu
Summary: Chiral oxindoles are important chemical structures found in many natural products. While there are well-developed methods for constructing C3 quaternary oxindoles with high selectivity, the efficient synthesis of chiral 3-substituted tertiary oxindoles is rarely reported. In this study, a multicomponent assembly method for complex oxindoles through enantioselective cooperative catalysis is presented.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Raffaella Mancuso, Melania Lettieri, Ida Ziccarelli, Patrizio Russo, Antonio Palumbo Piccionello, Bartolo Gabriele
Summary: A catalytic carbonylative approach is presented for the multicomponent synthesis of benzothiophene derivatives, based on an S-cyclization-demethylation-alkoxycarbonylation-reduction sequence promoted by the PdI2/KI catalytic system under relatively mild conditions. Benzothiophene-2-acetic esters are obtained in moderate to good yields starting from variously substituted substrates in combination with different alcohols as external nucleophiles.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Zhenhao Zhang, Nazarii Sabat, Gilles Frison, Angela Marinetti, Xavier Guinchard
Summary: This study presents a new gold(I) catalyst for highly enantioselective multicomponent reactions between aldehydes, hydroxylamines, and cyclic yne-enones. The method shows broad applicability and achieves high yields, total diastereoselectivity, and high enantiomeric excess.
Article
Biochemistry & Molecular Biology
Natalia A. Danilkina, Ekaterina A. Khmelevskaya, Anna G. Lyapunova, Alexander S. D'yachenko, Alexander S. Bunev, Rovshan E. Gasanov, Maxim A. Gureev, Irina A. Balova
Summary: The scope and limitations of the Nicholas-type cyclization for the synthesis of 10-membered benzothiophene-fused heterocyclic enediynes with different functionalities were investigated. Among the investigated conditions, cyclization via an arenesulfonamide functional group was found to be the most promising, yielding high overall yields. The acylated 4-aminobenzenesulfonamide nucleophilic group was found to be the most convenient for the synthesis of functionalized 10-membered enediynes bearing a clickable function. The synthesized cyclic enediynes exhibited moderate activity against lung carcinoma cells.
Article
Chemistry, Organic
Ju Eun Jeon, Siyeon Jeong, Hayeon Kwak, Jung Min Joo
Summary: In this study, gold(III)-catalyzed cyclization reactions of alkynyl norbornene derivatives were developed to generate benzofused (hetero)arenes with substitutions at the benzocyclic ring. The combination of Au(OAc)(3) and AgNTf2 allowed for the annulation of (hetero)arenes by intramolecular hydro(hetero)arylation followed by retroDiels-Alder reactions to afford fully conjugated benzofused (hetero)arenes in higher yields than the previously developed Pd(OAc)(2)-catalyzed protocol. Additionally, using AuCl3 instead of Au(OAc)(3) led to a rearrangement of (hetero)arenes with the norbornene bridge installed at the more electron-rich and sterically demanding position to afford the corresponding regioisomeric products in a divergent manner. These results highlight the importance of steric effects in addition to the electronic effects of the catalyst and the substrate on the rearrangement.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Xiao-Wen Zhang, Ming-Hui Zhu, Hai-Xiang Zeng, Qi-Yang Li, Wen-Bo Liu
Summary: This study presents a highly enantioselective NiH-catalyzed hydrocyclization of alkynones, yielding an array of enantioenriched heterocyclic tertiary allylic alcohols. The choice of precatalysts significantly influences the selectivity of the products, with yields reaching up to 81%.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Tamal Ballav, Rajesh Chakrabortty, Aniruddha Das, Suman Ghosh, Venkataraman Ganesh
Summary: This review summarizes the research achievements in the field of synergistic dual catalysis in recent years, highlighting the unique strategies of carbon-carbon and carbon-heteroatom bond formation achieved by combining Pd catalyst with transition metals, Lewis acids, or organocatalysts. The wide applications of these strategies in pharmaceutical and agrochemical industries are also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
