Review
Chemistry, Physical
Robert Francke, R. Daniel Little
Summary: Electrochemical catalysis is a valuable method for conducting redox-neutral reactions at mild conditions. It involves injecting electrons or holes into the reactant to induce chemical transformations. Recent advances have been made in understanding the mechanisms and developing new applications in this field. This contribution summarizes the recent progress in electrochemical catalysis.
CURRENT OPINION IN ELECTROCHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Johanna Proessdorf, Christian Jandl, Thomas Pickl, Thorsten Bach
Summary: It was found that while 2-alk-omega-enyloxy-sustituted benzaldehydes do not display any photochemical reactivity at the arene core, the respective iminium perchlorates undergo efficient reactions under certain conditions, leading to products with different molecular structures and stereochemical features.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Michio Yamada, Yuta Uokawa, Shino Sasaki, Naohiro Iha, Yoshihisa Hashimoto, Yuya Nagasaki, Yutaka Maeda, Mitsuaki Suzuki
Summary: The physicochemical properties of fullerene-based materials can be influenced by the type and mode of addition of functional groups. Developing fullerene derivatives with novel structures is crucial for the advancement of materials science. This study presents an efficient one-step strategy for synthesizing cyclobutene-annulated fullerene derivatives and characterizing their electronic properties.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Michio Yamada, Yuta Uokawa, Shino Sasaki, Naohiro Iha, Yoshihisa Hashimoto, Yuya Nagasaki, Yutaka Maeda, Mitsuaki Suzuki
Summary: In this study, a one-step strategy for synthesizing cyclobutene-annulated fullerene derivatives (cyclobutenofullerenes) was developed and their electronic properties were characterized. Despite steric strain, cyclobutenofullerenes can be easily prepared through a one-step reaction of C-60 with a secondary propargylic phosphate. Structural analysis of reaction intermediates suggests that the cascade reaction proceeds through a formal [2 + 2] cycloaddition of C-60 with an allene, caused by the 1,3-migration of the propargylic phosphate, followed by an additional 1,3-migration and subsequent 1,2-elimination of the phosphodiester moiety.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Pei-Pei Xu, Su-Ge Xin, Xue Li, Cui Liang, Dong-Liang Mo
Summary: We developed a copper(II)-catalyzed [3+2] cycloaddition reaction between N-aryl-alpha,beta-unsaturated nitrones and disubstituted allenoates to prepare a variety of [1,3]oxazino[3,2-a]indolines and dihydropyrido[1,2-a]indolines in moderate to excellent yields. Mechanistic studies revealed the kinetic preference for [1,3]oxazino[3,2-a]indoline and the thermodynamic preference for dihydropyrido[1,2-a]indoline. The reaction can be easily scaled up and chiral dihydropyrido[1,2-a]indoline can be obtained using a chiral auxiliary. The method demonstrates broad substrate scope, good functional group tolerance, and high diastereoselectivity, making it highly significant.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Ming Bao, Karlos Lopez, Raj Gurung, Hadi Arman, Michael P. Doyle
Summary: A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is achieved via a one-pot cascade reaction catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate. The reaction proceeds under mild conditions and provides the desired products in high yields and enantioretention. Furthermore, these dihydro-3H-carbazole-2-carboxylates can be transformed into decarboxylated compounds through hydrolysis and decarboxylation under unexpectedly mild reaction conditions, giving moderate yields with high retention of enantiomeric purity.
Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Ming Bao, Karlos Lopez, Raj Gurung, Hadi Arman, Michael P. Doyle
Summary: A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is achieved via a one-pot cyclopentannulation-rearrangement cascade reaction. The reaction is catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate, and involves the use of 3-methylindole and non-racemic donor-acceptor cyclopropanes. The resulting products show high yields and enantioretention under mild reaction conditions, and further transformation into decarboxylated compounds can be achieved with moderate yields and high enantiomeric purity.
Article
Chemistry, Multidisciplinary
Guanqun Zhang, Abdullah S. Alshreimi, Laura Alonso, Alan Antar, Hsien-Cheng Yu, Shahidul M. Islam, Laura L. Anderson
Summary: A new method for the synthesis of 1-pyrrolines with high regio- and diastereoselectivity has been explored using N-alkenylnitrones and alkynes, with mechanistic studies providing insight into the balance of steric and electronic effects that control the product preferences. This cascade reaction demonstrates the divergent synthetic utility of the new method through diastereoselective derivatization of the 1-pyrrolines prepared.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lu-Yu Cai, Xiu-Qing Song, Kuo Wang, Yue Zhang, Hong-Wu Zhao
Summary: The decarboxylative 1,4-addition reaction of benzofuran-based azadienes with allyl phenyl carbonates was efficiently catalyzed by Pd(OAc)(2)/dppf/Na2CO3, giving the desired products in good yields. The chemical structure of the target compounds was confirmed by single crystal X-ray structural analysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Hui-Hui Wu, Xiao-Zu Fan, Zhe Tang, Heng Zhang, Lu-Yu Cai, Xiao-Fan Bi, Hong-Wu Zhao
Summary: Under specific reaction conditions, the (5 + 6) cycloaddition of vinylethylene carbonates with isatoic anhydrides proceeded smoothly, yielding medium-sized N,O-containing heterocycles in reasonable chemical yields, as confirmed by X-ray diffraction analysis.
Article
Chemistry, Multidisciplinary
Nicolaj Inunnguaq Jessen, Maksimilian Bura, Giulio Bertuzzi, Karl Anker Jorgensen
Summary: An efficient and stereoselective synthesis of chiral cycl[3.2.2]azines has been achieved through the rational design and utilization of novel (E)-3-benzylidene-3H-pyrrolizines in iminium-ion catalysis. The method allows for incorporation of diverse enals and the obtained products can undergo selective transformations while retaining stereochemical information established in the [8+2] cycloaddition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Wuttichai Natongchai, Jesus Antonio Luque-Urrutia, Chalida Phungpanya, Miquel Sola, Valerio D'Elia, Albert Poater, Hendrik Zipse
Summary: The study discovered that highly nucleophilic 3,4-diaminopyridines can serve as effective catalysts for the cycloaddition of CO2 to epoxides, enhancing catalytic activity and promoting crucial reaction steps. Additionally, the research also demonstrated that the nucleophilic scaffold of 3,4-diaminopyridines can be used as a recyclable heterogeneous catalyst supported on polystyrene.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Xiao-Ting Qin, Ning Zou, Xiao-Ling Cheng, Cui Liang, Dong-Liang Mo
Summary: A variety of chiral nine-membered N-heterocycles were prepared in moderate to good yields with high diastereoselectivity through a silver(I)-catalyzed reaction. Experimental studies showed that the silver catalyst promoted the cycloaddition and rearrangement process, and controlled the stereochemistry of the products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
