Article
Chemistry, Organic
Shuheng Xu, Linwei Zeng, Sunliang Cui
Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.
Article
Chemistry, Multidisciplinary
Yoshifumi Hashikawa, Hui Li, Yasujiro Murata
Summary: This study focuses on the Diels-Alder reaction of C-60 with azines, providing important insights into the formation of bisfulleroids. The benzoannulation to the pyridazine ring resulted in significantly shortened reaction time and better interaction with C-60. Contrary to expectations, the benzobisfulleroid was converted into corresponding orifice-enlarged derivative slightly faster through photooxygenation.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Shuang Qiu, Xin Zhang, Chaopeng Hu, Hongxu Chu, Qianli Li, David A. Ruiz, Liu Leo Liu, Chen-Ho Tung, Lingbing Kong
Summary: In this study, we reveal the reactivity of aryliminoboranes via BNCC π conjugation, enabling the dearomative Diels-Alder-like reactions with aldehydes. This reaction features mild conditions, catalyst-free, and exhibits a broad substrate scope and good functional group tolerance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Xuejian Zhang, Burin Sudittapong, Michael D. D. Ward
Summary: This article describes a Co-12 coordination cage with a cuboctahedral architecture that exhibits strong guest binding of large aromatic fluorophores. The cage also catalyzes reactions of the bound guests and demonstrates a new type of cage-based catalysis that relies on Co(ii)/Co(iii) redox activity. These findings highlight the active role of the cage in catalytic processes, going beyond its passive function as a reaction vessel.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Khaled Youssef, Magali Allain, Thomas Cauchy, Frederic Gohier
Summary: 2-Bromo, 3-bromothiophene, 2,5-dibromothiophene, 3,4-dibromothiophene, and perbrominated thiophene were oxidized under different conditions to form thiophene S,S-dioxide. Depending on the substitution, sulfone was obtained when the hindered thiophene was used. However, monosubstituted thiophenes could not be transformed into sulfone due to the reactivity of the sulfoxide intermediate, which led to dimerization. The structures were confirmed through the obtaining of crystals. The oxidation of 3,4-dibromothiophene could either result in the formation of cycloadduct or the isolation of sulfone, which could further evolve into benzothiophene sulfone.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rebecca L. Spicer, Helen M. O'Connor, Yael Ben-Tal, Hang Zhou, Patrick J. Boaler, Fraser C. Milne, Euan K. Brechin, Guy. C. Lloyd-Jones, Paul J. Lusby
Summary: Coordination cage catalysis is a strategy that utilizes a cage as an exogenous catalyst, rather than relying on the endogenous binding of substrates. The cage alters the properties of a cofactor guest, which then transfers reactivity to the bulk-phase to catalyze reactions.
Article
Chemistry, Organic
Jonathan P. Knowles, Hannah G. Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn
Summary: This method transforms simple starting materials into complex tetracyclic products with potential medicinal chemistry applications through a sophisticated chemical catalysis process.
Article
Chemistry, Multidisciplinary
Qiuyu He, Lirong Cao, Yiran Wei, Gregory R. Dake
Summary: The utility of 2-diphenylphosphoryloxy-1,3-dienes for constructing substituted nitrogen heterocycles is demonstrated. These dienes undergo boron trifluoride-promoted aza-Diels-Alder reactions with imines or related species formed in situ using aldehydes and amine derivatives. The stability of the dienes allows for a three-component reaction without the need for special precautions. The enol phosphate functional group is highlighted for further reactions, generating functionalized piperidenes or pyridines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A new compound was synthesized successfully in this study by using Yb-(OTf)(3) catalyst to react donor-acceptor cyclopropanes with sulfur-containing 4π components. The reaction showed high yields and moderate to good diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Victor Laina-Martin, Jose A. Fernandez-Salas, Jose Aleman
Summary: Cycloaddition reactions, particularly Diels-Alder reactions, are regarded as powerful methodologies for building carbon-carbon bonds. The inverse-electron-demand hetero-Diels-Alder reactions have been a significant breakthrough for synthesizing heterocyclic compounds. Among them, the organocatalytic enantioselective version has been extensively studied due to its asymmetric construction of diversely functionalized scaffolds under green chemistry conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Courtney Ngai, Bryce da Camara, Connor Z. Woods, Richard J. Hooley
Summary: A self-assembled Fe4L6 cage with internally oriented carboxylic acid functions can catalyze a variety of dissociative nucleophilic substitution reactions, showing strong selectivity for specific substrate shapes. The reactivity of the cage is highly influenced by even small structural differences in reactants, indicating a complex control of catalytic behavior.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Grzegorz Mloston, Katarzyna Urbaniak, Malwina Sobiecka, Heinz Heimgartner, Ernst-Ulrich Wuerthwein, Reinhold Zimmer, Dieter Lentz, Hans-Ulrich Reissig
Summary: The hetero-Diels-Alder reactions of in situ-generated azoalkenes with thioketones provide an efficient and regioselective method for synthesizing scarcely known N-substituted 1,3,4-thiadiazine derivatives. The high regioselectivity observed is attributed to kinetic reaction control, with sterically less unhindered thiones undergoing (4 + 2)-cycloadditions via highly unsymmetric transition states. In the case of highly hindered thioketones, a zwitterionic intermediate with a fully formed C-S bond was detected, leading to the formation of 1,3,4-thiadiazine derivatives in a second step.
Article
Polymer Science
Paul van den Tempel, Emiel O. van der Boon, Jozef G. M. Winkelman, Antonina V. Krasnikova, Daniele Parisi, Peter J. Deuss, Francesco Picchioni, Ranjita K. Bose
Summary: The furan-maleimide Diels-Alder chemistry is a useful tool for designing thermo-reversible click networks. In this study, a new reaction in furan-maleimide click networks, called the Double-Diels-Alder reaction (DDA), was reported. This reaction forms extra linkages between Diels-Alder adducts and non-reacted furan groups, resulting in stronger materials but reducing thermal recycling efficiency. The study revealed that the DDA reaction can occur in both intramolecular and intermolecular fashion, and it exhibits reversibility like the regular Diels-Alder reaction. The importance of the DDA reaction in furan-maleimide click networks may be easily overlooked, leading to unexpected reactivity in these systems.
Article
Green & Sustainable Science & Technology
Przemystaw Wolinski, Agnieszka Kacka-Zych, Barbara Mirostaw, Ewelina Wielgus, Aleksandra Olszewska, Radomir Jasinski
Summary: In this study, a new green procedure for the synthesis of a series of 1,2-oxazine N oxide moieties via Hetero Diels-Alder (HDA) reaction was described, using (2E)-3-aryl-2-nitroprop-2-enenitriles. Unlike most known HDA reactions, this process does not require a Lewis acid-type catalyst, operates under mild conditions, and exhibits full atomic economy and selectivity. Additionally, the reaction process was characterized using Molecular Electron Density Theory (MEDT).
JOURNAL OF CLEANER PRODUCTION
(2022)
Article
Chemistry, Multidisciplinary
M. Malavolti, A. Brandi, A. Salvini, D. Giomi
Article
Chemistry, Multidisciplinary
Donatella Giomi, Renzo Alfini, Jacopo Ceccarelli, Antonella Salvini, Alberto Brandi
Article
Chemistry, Multidisciplinary
R. Oliva, M. A. Ortenzi, A. Salvini, A. Papacchini, D. Giomi
Article
Multidisciplinary Sciences
A. Papacchini, M. R. Telaretti Leggieri, L. Zucchini, M. A. Ortenzi, F. Ridi, D. Giomi, A. Salvini
ROYAL SOCIETY OPEN SCIENCE
(2018)
Review
Chemistry, Medicinal
Franca M. Cordero, Donatella Giomi, Alberto Brandi
CURRENT TOPICS IN MEDICINAL CHEMISTRY
(2014)
Article
Chemistry, Organic
Donatella Giomi, Renzo Alfini, Alessandra Micoli, Elisa Calamai, Cristina Faggi, Alberto Brandi
JOURNAL OF ORGANIC CHEMISTRY
(2011)
Article
Polymer Science
Rosangela Oliva, Federica Albanese, Giacomo Cipriani, Francesca Ridi, Donatella Giomi, Marino Malavolti, Lorenza Bernini, Antonella Salvini
JOURNAL OF POLYMER RESEARCH
(2014)
Article
Chemistry, Organic
Donatella Giomi, Renzo Alfini, Alberto Brandi
Article
Chemistry, Organic
Renzo Alfini, Elisa Calamai, Antonella Salvini, Donatella Giomi
Article
Chemistry, Multidisciplinary
Antonella Salvini, Donatella Giomi, Giacomo Cipriani, Giovanni Bartolozzi, Renzo Alfini, Alberto Brandi
Article
Chemistry, Multidisciplinary
Donatella Giomi, Marino Malavolti, Oreste Piccolo, Antonella Salvini, Alberto Brandi
Article
Chemistry, Multidisciplinary
Donatella Giomi, Jacopo Ceccarelli, Antonella Salvini, Alberto Brandi
Article
Chemistry, Multidisciplinary
Donatella Giomi, Jacopo Ceccarelli, Antonella Salvini, Marika Pinto, Alberto Brandi
Summary: The reduction of aromatic nitro compounds can be efficiently achieved using Wang-PQM catalyst and NaBH4, leading to high yields of azo and/or hydrazoarenes.
Article
Chemistry, Multidisciplinary
Donatella Giomi, Antonella Salvini, Jacopo Ceccarelli, Alberto Brandi
Summary: Bromotrimethylsilane (TMSBr) is an efficient reagent for the solvent-free conversion of glycerol into bromohydrins, as well as for catalyzing transesterification of castor oil to produce FAME in acidic conditions. Depending on the reaction conditions, glycerol can be selectively converted into alpha-monobromohydrin (1-MBH) or alpha,gamma-dibromohydrin (1,3-DBH) in good yields.
Article
Chemistry, Multidisciplinary
Donatella Giomi, Jacopo Ceccarelli, Alberto Brandi