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, 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
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, Multidisciplinary
Hongbo Qi, Kaiming Han, Shufeng Chen
Summary: This study presents a convenient palladium-catalyzed domino cyclization reaction for the synthesis of bis(benzofuranyl)methane scaffolds bearing all-carbon quaternary center, in which multiple bonds and rings are formed in a single synthetic sequence through a cascade reaction. The approach demonstrates broad substrate scope and good functional-group tolerance, and has been successfully applied to the synthesis of benzofuranyl methyl chromane derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Peter Langer
Summary: The domino reactions of heterocyclic enamines with chromone derivatives lead to the synthesis of a variety of annulated heterocyclic ring systems, with the reaction pathway depending on the substituent at position 3 of the chromone. Functional groups at the carbonyl group of the chromone at position 3 allow for further synthetic transformations, including additional ring closures.
Article
Chemistry, Physical
Bo-Han Zhu, Ying-Qi Zhang, Hao-Jin Xu, Long Li, Guo-Cheng Deng, Peng-Cheng Qian, Chao Deng, Long-Wu Ye
Summary: An efficient copper-catalyzed tandem alkyne hydration/intramolecular Mannich reaction has been investigated for the synthesis of valuable compounds. This method allows the efficient synthesis of 3,4-dihydro-2-quinolones with high regio-, diastereo-, and enantioselectivity.
Review
Chemistry, Physical
Bartolo Gabriele, Raffaella Mancuso, Nicola Della Ca, Lucia Veltri, Ida Ziccarelli
Summary: This article provides an overview of catalytic carbonylative double cyclization reactions, where organic substrates and carbon monoxide are sequentially activated to form two new cycles with the incorporation of carbon monoxide. It highlights the power of this synthetic methodology in the one-step synthesis of complex molecular architectures using readily available CO as the building block. The review is divided into five sections: Introduction, Functionalized Olefinic Substrates, Functionalized Acetylenic Substrates, Functionalized Halides, and Conclusions and Future Perspectives.
Article
Chemistry, Physical
Nerea Conde, Maria Teresa Herrero, Garazi Urgoitia, Raul SanMartin
Summary: Metal-catalyzed cascade processes based on hydrofunctionalization of alkynes have the potential to provide advantageous approaches to otherwise synthetically challenging compounds. A CNN pincer palladium(II) complex, acting as a homogeneous catalyst, provides the corresponding polyheterocycles with a higher substrate/catalyst ratio.
Article
Chemistry, Applied
Da-Ping Jin, Shi-Qi Cao, Fu Cheng, Ze-Sen Xue, Run-Ze Li, Yan-Lin Pu, Dao-Yong Zhu, Wen Bao, Xue-Tao Xu, Shao-Hua Wang
Summary: An Au(I)-catalyzed cascade reaction involving cyclization and semipinacol rearrangement of 1,6-enynes has been developed for the synthesis of spiro[4.5]decanes and 7-azaspiro[4.5]decanes. The use of JohnPhosAuCl/NaBARF catalyst led to the formation of functionalizable spirocyclic products with high diastereoselectivity ranging from 6.7:1 to > 20:1 dr. A plausible reaction mechanism has been proposed based on previous literature and experimental findings.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Joseph A. Kaplan, Suzanne A. Blum
Summary: A method is developed for producing regio- and stereodefined trisubstituted iodoalkenes by diverting intermediates from an iodination-electrophilic-cyclization mechanism. The method involves the ring-opening of cyclized sulfonium ion-pair intermediates with nucleophilic iodide to form alkenes. The isolation of the sulfonium ion-pair intermediate allows access to complementary reactivity and the products serve as synthetic building blocks.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Nengneng Zhou, Qiankun Xu, Ziqin Xia, Kaimo Kuang, Sixin Wu, Wenping Li, Man Zhang
Summary: In this study, a novel palladium-catalyzed radical cascade reaction was developed for the synthesis of cyanoalkylsulfone-containing cyclopenta[gh]phenanthridines. The reaction involved the cleavage of a C-C single bond and insertion of SO2, and showed mild reaction conditions, a broad substrate scope, and high functional group tolerance.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Yin Xu, Gan-Lu Qian, Da-Qiu Cui, Peng-Cheng Qian, Chao-Yue Zhao, Xin Hong, Bo Zhou, Long-Wu Ye
Summary: Herein, a chiral Bronsted acid-catalyzed desymmetrization reaction of diynes is reported, providing a facile access to enantioenriched 1,3-diaminopropanol derivatives and γ-butyrolactones with high enantioselectivities. These products can be used as precursors for the synthesis of versatile N- and O-heterocycles, which are important structural cores of bioactive molecules. Control experiments and theoretical calculations are used to confirm the mechanism and elucidate the origin of enantioinduction.
