Article
Chemistry, Organic
Lei Dai, Zhou Zhang, Guangzhou Zhu, Yun Liu, Xiaoqin Liu, Jinpeng Zhang, Liangce Rong
Summary: This article describes the Selectfluor-promoted vicinal fluorohydroxylation and hydration reaction of para-quinone methides (p-QMs), which affords vicinal fluorohydrins and ketone/ether products in high yields. The electronic properties of substituents in the aromatic ring highly control the hydration products, and the amount of Selectfluor is significantly different during the synthesis of ketone/ether products. This reaction also marks the first fluorohydroxylation of p-QMs, and the wide range of p-QMs makes the vicinal fluorohydroxylation of great significance.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Yu-Chen Wei, Liang-Yan Hsu
Summary: This article demonstrates that quantum electrodynamic (QED) effects can significantly enhance the rate of electron transfer (ET) without the use of cavities. By incorporating the effect of infinite one-photon states into Marcus theory and introducing the concept of electron transfer overlap, the study provides new insights into the involvement of cavity-free QED effects in ET reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Austin S. Flemming, Brendan C. Dutmer, Thomas M. Gilbert
Summary: Systematic computational studies were conducted to investigate the pericyclic Diels-Alder reactions between (H3C)2C=C(CH3)2 and various substituted cyclopentadienes. The effects of substitution on Gibbs free energy barrier heights and reaction Gibbs free energies were analyzed. The results showed that the substitution effects were additive, and the impacts on barriers varied depending on the position and type of substitution. The generated Gibbs free energy correction values are useful for predicting the reaction rates and product stability.
Article
Chemistry, Multidisciplinary
Saul Alberca, Esteban Matador, Javier Iglesias-Siguenza, Ma de Gracia Retamosa, Rosario Fernandez, Jose M. Lassaletta, David Monge
Summary: Alpha-keto hydrazones and alpha,beta-unsaturated gamma-keto hydrazones are suitable pro-nucleophiles for asymmetric cross-aldol reactions. A quinidine-derived primary amine catalyst yields tertiary trifluoromethylated alcohols with good-to-excellent yields and high enantioselectivities, leading to various appealing fluorinated compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Bingbin Zhu, Hang Han, Wei-Ke Su, Boan Yan, Zhi Li, Chuanming Yu, Xinpeng Jiang
Summary: A metal-free intramolecular carbofluorination protocol for the synthesis of tetrasubstituted monofluoroalkenes from internal alpha,beta-ynones and Selectfluor is reported, demonstrating high stereoselectivity and broad functional group tolerance. Chelation between tetrafluoroborate anion and the aldehyde group oxygen enhances stereoselectivity, with tetrafluoroborate serving as the direct fluorine source. Furthermore, the addition of sodium tetrafluoroborate allows for multiple reuse of Selectfluor without loss of reactivity.
Article
Chemistry, Applied
Amado Lacruz, Mireia Salvador, Miren Blanco, Karmele Vidal, Antxon Martinez de Ilarduya
Summary: This study successfully synthesized fluorine-free, low surface energy, and partially biobased (co)polymethacrylates, which were applied on cotton fabrics and showed good coating effects, significantly improving static water contact angles and solvent-water separation efficiencies. Textiles coated with (co)polymethacrylates with higher M3T contents exhibited better repellency to olive oil compared to those with lower contents. This may be attributed to the time-dependent evolution of the surface free energy and reorientation of stearyl side chains during contact with olive oil, as well as the reduced barrier properties of coatings with lower tris(trimethylsilyloxy)silyl side chain contents.
PROGRESS IN ORGANIC COATINGS
(2021)
Article
Chemistry, Multidisciplinary
Nicola Zappimbulso, Maria Annunziata M. Capozzi, Andrea Porcheddu, Gianluca M. Farinola, Angela Punzi
Summary: A new solvent-free method for the synthesis of Squaraines and croconaines was developed, which is a simple, cost-effective, and environmentally friendly approach. The protocols based on conventional thermal heating, mechanochemical milling, and IR-light activation were compared for the synthesis.
Article
Chemistry, Organic
Guowen He, Xuan Xiao, Han-Zhou Jin, Jin-Hong Lin, Tongsheng Zhong, Xing Zheng, Ji-Chang Xiao
Summary: This study presents a mild Ph2S/Selectfluor-promoted deoxydifluorination of aldehydes, which offers a safe and convenient alternative to previous methods using hazardous reagents. The protocol is attractive due to the use of easily available reagents and practical operations.
Article
Chemistry, Multidisciplinary
Jie Shen, Arundhati Roy, Himanshu Joshi, Laxmicharan Samineni, Ruijuan Ye, Yu-Ming Tu, Woochul Song, Matthew Skiles, Manish Kumar, Aleksei Aksimentiev, Huaqiang Zeng
Summary: In this study, we report a novel class of fluorofoldamer-based artificial water channels that have excellent water transport rate and selectivity, as well as structural simplicity and robustness. The best-performing channel is a decorated foldamer nanotube, which exhibits an ultrafast water conduction rate and can exclude salts and protons. The inwardly facing C(sp2)-F atoms in the channel are proposed to be critical for enabling the ultrafast and superselective water transport properties.
Article
Chemistry, Applied
Irene Tagliaro, Stefano Seccia, Beatrice Pellegrini, Sabrina Bertini, Carlo Antonini
Summary: One of the current challenges in materials science is to develop safe and sustainable coatings with enhanced functionalities, such as replacing fluorinated substances due to health concerns. This study proposes an innovative method for fabricating bio-based polymeric coatings using modified chitosan, with fine-tuning of transparency and superhydrophobicity properties. The process involves fluorine-free modification of chitosan and coating deposition using a solvent-free approach. The modified chitosan is characterized to confirm its functionality modification, and the deposition method allows control over coating properties while maintaining durability.
CARBOHYDRATE POLYMERS
(2023)
Review
Chemistry, Multidisciplinary
Karen J. Ardila-Fierro, Jose G. Hernandez
Summary: Mechanochemistry has become a widely accepted alternative for chemical synthesis due to its efficiency, practicality, and sustainability, satisfying multiple Principles of Green Chemistry.
Article
Chemistry, Multidisciplinary
Reagan L. Mohlala, E. Mabel Coyanis, Manuel A. Fernandes, Moira L. Bode
Summary: The reaction of benzimidazolone derivatives, or their thio- or aza-counterparts, with an isocyanide in the presence of acetone unexpectedly gave rise to novel tricyclic benzodiazepine derivatives in good yield. However, benzimidazole starting substrates bearing an electron-withdrawing group resulted in dihydroquinoxaline derivatives instead. The use of deuterated acetone instead of acetone significantly affected yield and reactivity in the four-component reaction but not in the three-component reaction.
Article
Chemistry, Organic
Francesca Franco, Sara Meninno, Alessandra Lattanzi, Alessandra Puglisi, Maurizio Benaglia
Summary: A continuous flow approach was developed for the synthesis of alpha-trifluoromethylthiolated esters and amides using commercially available arylacetic acids and N-(trifluoromethylthio)phthalimide as the electrophilic reagent. The telescoped process resulted in good overall yield and short reaction times for the formation of alpha-substituted SCF3 amides and esters.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kaitlyn M. Freiberg, Rahul D. Kavthe, Rohan M. Thomas, David M. Fialho, Paris Dee, Matthew Scurria, Bruce H. Lipshutz
Summary: This passage describes a new technology for generating amide and peptide bonds from carboxylic acids and amines without traditional coupling reagents. The one-pot processes rely on the formation of thioesters using a simple dithiocarbamate, which are safe, green, and inspired by nature, and then converted to the desired functionality.
Article
Chemistry, Multidisciplinary
Hazim M. Ali, Yasser A. El-Ossaily, Saoud A. Metwally, Ibrahim O. Althobaiti, Hamud A. Altaleb, Yousra A. Naffea, Mahmoud S. Tolba
Summary: A green and facile method was developed for the synthesis of pyrazole compounds, which exhibited notable antimicrobial activities.
