Article
Chemistry, Multidisciplinary
Meng-Yang Chang, Min-Chen Tsai, Chun-Yi Lin
Summary: The paper presents a one-pot facile route for the synthesis of functionalized flavones mediated by BiCl3/RuCl3, involving intermolecular ortho-acylation of substituted phenols with cinnamoyl chlorides, and intramolecular cyclodehydrogenation of the resulting o-hydroxychalcones. The reaction conditions are discussed.
Article
Chemistry, Multidisciplinary
Erlin Yue, Lea Dettling, Julian A. W. Sklorz, Selina Kaiser, Manuela Weber, Christian Mueller
Summary: The novel tosyl- and mesitylsulfonyl-substituted triazaphospholes were synthesized and characterized. The results presented here provide a new strategy for selectively preparing such coordination compounds in a one-pot approach.
CHEMICAL COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Ye Eun Kim, Hyunsung Cho, Yoo Jin Lim, Chorong Kim, Sang Hyup Lee
Summary: This study presented the one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations. The optimized conditions for the reaction were discussed, focusing on the alkylation step and the formation of intermediates. The significance lies in the development of efficient one-pot reactions and the generation of new 1-alkoxyindoles.
Article
Chemistry, Organic
Bumpei Maeda, Yusuke Aihara, Ayato Sato, Toshinori Kinoshita, Kei Murakami
Summary: This article describes a photoinduced benzylic C-H thiocyanation method. A series of alkyl thiocyanates were efficiently synthesized using Selectfluor as the oxidant, and one-pot isothiocyanation was achieved following the C-H thiocyanation. The resulting thiocyanates and isothiocyanates can be applied to the divergent transformation of pharmaceuticals.
Article
Materials Science, Multidisciplinary
Priyanka Phalswal, P. K. Khanna
Summary: The microwave-assisted synthesis of MoO2 nanoparticles using a home microwave oven proved to be effective, yielding nearly phase pure nanostructured MoO2 with particle diameter of less than 14 nm.
Article
Chemistry, Organic
Kai N. Sands, Benjamin S. Gelfand, Thomas G. Back
Summary: Aryl selenonic acids were synthesized from aryl bromides via a one-pot method, with yields ranging from 77-90%. The synthesis involved metalation, selenation, oxidation with hydrogen peroxide, and ion exchange. One derivative readily dehydrated to form a cyclic selenonic ester, while two minor byproducts were identified as mixed salts of aryl selenonic acids with either aryl seleninic or selenious acid through X-ray crystallography.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Materials Science, Multidisciplinary
Andrzej Huczko, Agnieszka Dabrowska, Michal Bystrzejewski, P. Baranowski, Santosh K. Tiwari, Lukasz Dobrzycki, Maciej Fronczak, Manoj Pandey, Rabi Sharan Bogati, Bhim Kafle, Deepak Prasad Subedi
Summary: A novel and facile protocol for the fast and autothermal formation of different types of nanocarbons including 3D graphene-like nanosystem via combustion synthesis is presented in this study. The combustion reaction of magnesiothermic reduction of carbon-bearing oxidants resulted in the total conversion to solid raw products containing mostly nanocrystalline magnesium oxide, porous carbon, and layered graphene-related nanomaterial. Purification in mineral acid removed the MgO and non-reacted reducer, enabling efficient recovery of the carbon product.
DIAMOND AND RELATED MATERIALS
(2022)
Article
Chemistry, Physical
Mingxin Liu, Zewen Wu, Xianghua Kong, Xu Zhang, Lida Tan, Hong Guo, Chao-Jun Li
Summary: The generation of BTX compounds from non-petroleum feedstocks is important for chemists in terms of sustainability. A novel synthesis of toluene catalyzed by GaN semiconductor nanowire arrays is reported, which can facilitate the generation of toluene from methane and methanol under both photo-irradiation and thermal conditions. Detailed computational studies revealed different mechanisms for photo- and thermal toluene synthesis.
Article
Chemistry, Physical
Mingxin Liu, Zewen Wu, Xianghua Kong, Xu Zhang, Lida Tan, Hong Guo, Chao-Jun Li
Summary: A novel synthesis of toluene using GaN semiconductor nanowire arrays as catalyst is reported. The GaN nanowire arrays can synergistically facilitate the facile generation of toluene from methane and methanol under photo-irradiation or thermal conditions. Detailed computational studies revealed different mechanisms involved in the photo- and thermal-toluene synthesis.
Article
Chemistry, Organic
Antonio Guirado, Bruno Martiz, Maria Vera, Raquel Andreu, Delia Bautista
Summary: New convenient synthetic methods have been developed for the synthesis of pyrazoline and pyrazolooxazine starting from 2,2-dichlorovinylacetophenones. The reaction of 2,2-dichlorovinylacetophenones with 2-hydroxyethylhydrazine gives high yields of previously unknown 3-aryl-5-dichloromethyl-1-(2-hydroxyethyl)-2-pyrazolines. These compounds can undergo cyclization to afford 2-aryl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazines and can also be obtained in near quantitative yields through a one-pot preparative process. The simplicity and high yield of this reaction make it more attractive than previously described methods.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Feng Ma, Xian-Tao Wu, Le-Wei Miao, Fuxing Sun, Yi-Jun Jiang, Peng Chen
Summary: A general, efficient, and regioselective protocol for the synthesis of trifluoromethylated bis(carbazolyl)methanes has been developed. This metal-free transformation proceeds smoothly under air atmosphere and has a broad scope for both reaction partners. This method can also be extended to the synthesis of difluoromethylated and chlorodifluoromethylated bis(carbazolyl)methanes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Kazuto Takaishi, Ritsuki Nishimura, Yuha Toda, Hajime Morishita, Tadashi Ema
Summary: Catalytic CO2 reduction with phenylsilane under solvent-free conditions was utilized to synthesize 3,4-dihydropyrans from beta dicarbonyl compounds and styrenes in a one-pot reaction. The synthesis involves three steps: (1) formation of bis(silyl)acetal from CO2 and phenylsilane, followed by a domino reaction of (2) Knoevenagel condensation and (3) inverse-electron-demand oxa-Diels-Alder reaction. The first step is catalyzed by a pentanuclear ZnII complex (0.07 mol %) to generate bis(silyl)acetals, which are then hydrolyzed into formaldehyde for the second step.
Article
Chemistry, Physical
Alberto Castellano-Soria, Jesus Lopez-Sanchez, Cecilia Granados-Miralles, Maria Varela, Elena Navarro, Cesar Gonalez, Pilar Marin
Summary: Fe3C/few-layered graphene core/shell nanoparticles embedded in a carbon matrix are synthesized using a novel surfactant sol-gel strategy. The resulting product shows high magnetic response and chemical stability.
JOURNAL OF ALLOYS AND COMPOUNDS
(2022)
Article
Chemistry, Applied
Mohammad Bagher Teimouri, Zahra Bozorgpour Savadjani, Morteza Shiri, Rahman Bikas, Soheila Naderi
Summary: A new class of quinone dyes, xanthoquinones, have been synthesized through a cycloaddition reaction, resulting in a specific structure of xanthone and quinone subunits.
Article
Chemistry, Multidisciplinary
Ioan Bitcan, Alessandro Pellis, Andreea Petrovici, Diana-Maria Dreava, Iulia Pausescu, Francisc Peter, Lajos Nagy, Lucia Gardossi, Anamaria Todea, Sandor Keki
Summary: The synthesis of bio-based poly(5-hydroxymethyl-2-furancarboxylate-co-ricinoleate) was investigated using green biocatalytic pathways either from ricinoleic acid and 5-hydroxymethyl-2-furancarboxylic acid or directly from castor oil. The reactions were carried out under different conditions, and the resulting products were evaluated for their molecular weight and thermal properties.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2023)
Article
Chemistry, Multidisciplinary
Moritz E. Hansen, Samuel O. Yasmin, Susanne Wolfrum, Erick M. Carreira
Summary: The first total syntheses of tricyclic mutanobactins A and B, lipopeptides incorporating a thiazepanone, isolated from Streptococcus mutans, a member of the human oral microbiome, were reported. These natural products were rapidly delivered through a cascade of cyclization reactions using a solid-phase peptide synthesis (SPPS) based route. This versatile process was also used for a streamlined synthesis of mutanobactin D. Additionally, an independent synthesis of a truncated mutanobactin A analog, utilizing a novel thiazepanone amino acid building block, was provided.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Benedikt S. Schreib, Jacopo Margarini, Erick M. Carreira
Summary: The synthesis of picolinamides through Ritter reaction of 2-cyanopyridine with alcohols and alkenes is reported, and a range of additional heteroaryl nitriles successfully participate in the amidation reaction. The salient features of this reaction include operational simplicity and the use of inexpensive reagents. The synthetic utility of a camphene derived picolinamide is demonstrated through a palladium-catalyzed C-H arylation reaction.
Article
Chemistry, Multidisciplinary
Willi M. Amberg, Erick M. Carreira
Summary: This study presents the total synthesis of the complex molecule (+)-aberrarone using an Au-catalyzed-Sn-mediated cascade reaction, which efficiently closes four rings in the molecule. The method offers a stereoselective approach to synthesizing the natural product with a unique tetracyclic skeleton.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Viktoria C. Gerken, Erick M. Carreira
Summary: Graphitic carbon nitride (g-C3N4) is a photocatalyst used in the Giese reaction, showing excellent reusability and stability over five cycles with no changes in composition or morphology.
Article
Chemistry, Multidisciplinary
Nils Trapp, Michael Worle, Bernd Kuhn, Paul Gerber, Raffael Vorberg, Erick M. M. Carreira, Klaus Mueller
Summary: The molecular and crystal structures of 19 N-alkyl-substituted pipecolamide derivatives, including partial fluorination patterns, were presented. The different fluorination patterns in the N-alkyl group resulted in diastereomeric compounds with distinct crystal and molecular structures. The study also revealed an extraordinary conformational diversity in the various N-alkylpiperidine units, and provided insight into consistent conformational patterns and their modulation factors.
HELVETICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Supratim Ghosh, Avtar Changotra, David A. Petrone, Mayuko Isomura, Erick M. Carreira, Raghavan B. Sunoj
Summary: In this study, the mechanism of a chiral Ir-phosphoramidite-catalyzed asymmetric reductive deoxygenation reaction was investigated using density functional theory. It was found that Bi(OTf)3 promotes ionic and noncovalent interactions, which play a crucial role in nucleophile selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
David M. Fischer, Henry Lindner, Willi M. Amberg, Erick M. Carreira
Summary: Intermolecular cyclopropanation of mono-, di-, and trisubstituted olefins with alpha-bromo-beta-ketoesters and alpha-bromomalonates under organophotocatalysis is reported. The transformation exhibits broad functional group tolerance, producing highly substituted cyclopropanes. Mechanistic investigations, including Stern-Volmer quenching, quantum yield determination, and deuteration experiments, provide insights into the catalytic cycle.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Marlene Fadel, Erick M. Carreira
Summary: The first total synthesis of (+)-pedrolide, a tigliane-derived diterpenoid featuring an unprecedented 5-5-6-6-3 carbon skeleton, was achieved. A key step in the synthesis involved the construction of the bicyclo[2.2.1]heptane core via an intramolecular cyclopentadiene-Diels-Alder cycloaddition. A norbornadiene was used as a surrogate for cyclopentadiene, and the unmasking of the cyclopentadiene was achieved through a complex Diels-Alder reaction cascade. This synthesis also provided a novel approach to a densely functionalized carane in an efficient and enantioselective manner.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Editorial Material
Chemistry, Multidisciplinary
Erick M. Carreira
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Sven M. Papidocha, Hendrik H. Bulthaupt, Erick M. Carreira
Summary: The first total synthesis of heavily oxidized cassane-type diterpenoids, neocaesalpin A, AA, and nominal neocaesalpin K, was achieved using a redox-flexible platform as a key intermediate. The synthesis involved an intermolecular Diels-Alder reaction and a novel late-stage oxidation method for furfuryl acetate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Henry Lindner, Willi M. Amberg, Erick M. Carreira
Summary: In this study, unactivated olefins are converted into alkyl azides using bench-stable NaN3 in the presence of FeCl3·6H2O under blue-light irradiation. The reaction exhibits anti-Markovnikov selectivity and can be conducted under mild ambient conditions in the presence of air and moisture.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Hendrik H. Bulthaupt, Fabian Glatz, Sven M. Papidocha, Chunyan Wu, Shawn Teh, Susanne Wolfrum, Lucia Balazova, Christian Wolfrum, Erick M. Carreira
Summary: This study reports the synthesis and enantioselectivity of a series of compounds, and reveals the stimulating effect of one of the compounds on the respiration of brown adipocytes, which has potential applications in obesity treatment.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
David M. Fischer, Manuel Freis, Willi M. Amberg, Henry Lindner, Erick M. Carreira
Summary: We have developed a method for difunctionalization of unactivated, terminal olefins using intermolecular addition of alpha-bromoketones, -esters, and -nitriles followed by formation of 4- to 6-membered heterocycles with pendant nucleophiles. The reaction can be conducted with alcohols, acids, and sulfonamides as nucleophiles, yielding products with 1,4 functional group relationships that can be further manipulated. The reaction employs a benzothiazinoquinoxaline organophotoredox catalyst at a low catalyst loading and is tolerant to air and moisture.
Article
Chemistry, Multidisciplinary
Monica Guberman, Miroslav Kosar, Anahid Omran, Erick M. Carreira, Marc Nazare, Uwe Grether
Summary: Labeled chemical probes are crucial for the development and commercialization of drugs. They play a significant role in various research phases and provide valuable tools for specific application needs. The reverse-design approach enables the generation of high-quality probes based on previously optimized small molecules, fostering collaborations between academia and industry.
Article
Chemistry, Multidisciplinary
David M. Fischer, Moritz Balkenhohl, Erick M. Carreira
Summary: The cycloisomerization of beta-, gamma-, and delta-unsaturated N-acyl sulfonamides to N-sulfonyl lactams and imidates using a CoIII(salen) catalyst with t-BuOOH or air as the oxidant is reported in this study. The method exhibits good functional group tolerance and provides a new class of cyclic building blocks. The strong solvent dependence of the transformation and the synthetic versatility of the N-sulfonyl imidate product class are highlighted.