Article
Chemistry, Applied
Natalia S. Soldatova, Artem V. Semenov, Kirill K. Geyl, Sergey V. Baykov, Anton A. Shetnev, Anna S. Konstantinova, Mikhail M. Korsakov, Mekhman S. Yusubov, Pavel S. Postnikov
Summary: A method for copper-catalyzed N-arylation of diverse oxadiazolones using diaryliodonium salts has been reported with high yields up to 92%. It was found that the steric effects in aryl moieties determined the chemoselectivity of arylations. Mesityl-substituted diaryliodonium salts demonstrated high potential as selective arylation reagents.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Organic
Sam J. Moons, Alexander D. Robertson, Thomas J. Boltje
Summary: A mild and efficient protocol for the removal of N-acetyl groups in biomolecules, such as aminosugars, is reported. The resulting amine can be functionalized in a one-pot manner.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Atsushi Umehara, Soma Shimizu, Makoto Sasaki
Summary: This report presents a general method for the direct N-acylation of N-heterocycles using the DMAPO/Boc(2)O system. This one-pot method allows for the synthesis of bulky N-acyl heterocycles from less nucleophilic N-heterocycles and sterically hindered carboxylic acids. The protocol has also been successfully applied to the one-pot N-acylation of 7-azaindoles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Li Yingxian, Chen Wei, Zhao Linchun, Zhang Ji-Quan, Zhao Yonglong, Li Chun, Guo Bing, Tang Lei, Yang Yuan-Yong
Summary: This study presents an atom economic protocol for the preparation of N-methyl amides using DABCO/Fe3O4 cooperative catalysis. The protocol is simple, compatible with a range of aliphatic and (hetero)aromatic acids, and achieves high yields.
Article
Multidisciplinary Sciences
Takanori Iwasaki, Kazuki Tsuge, Naoki Naito, Kyoko Nozaki
Summary: This study reports an Ir catalyst for the selective hydrogenolysis of urea derivatives, achieving the transformation of less reactive carbonyl compounds in the presence of more reactive ones. The proposed catalyst showed tolerance to highly reactive carbonyl groups such as ester, amide, and carbamate, and exhibited high chemoselectivity towards urea. This research provides a new strategy for the chemical recycling of polyurea resins.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Patrycja Mala, Christian Marcus Pedersen
Summary: N-Glycosyl N-sulfonyl amides were synthesized using self-promoted glycosylation without the need for catalysts or additives. The method allows for the selective beta-glycosylation of sulfonylated asparagine derivatives, providing access to glycosyl sulfonyl amides under mild conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Atsushi Umehara, Soma Shimizu, Makoto Sasaki
Summary: This report presents a practical and operationally simple method for the direct N-acylation of less nucleophilic heterocycles and amides with carboxylic acids. The method utilizes the DMAPO/Boc(2)O system and does not require pre-activation of substrates. It demonstrates high yield, excellent functional group tolerance, and broad substrate scope, making it suitable for both academic and industrial laboratories.
Article
Chemistry, Multidisciplinary
Yi Yang, Nathalie Saffon-Merceron, Julien C. Vantourout, Anis Tlili
Summary: We present a straightforward strategy for synthesizing unprecedented N-((trifluoromethyl)thio), N-(trifluoromethyl) amines using isothiocyanates, a fluoride source, and an electrophilic trifluoromethylthiolation reagent. The scalability of the methodology has been demonstrated, and the stability of the synthesized motif has been investigated.
Article
Chemistry, Physical
Pengxiang Gao, Song Liu, Jitao Yang, Dishun Zhao, Qingbin Liu
Summary: In this study, a solvent-free continuous flow bimetallic Pt/V catalytic hydrogenation method for N-methylpyrrolidone (NMP) to prepare N-methylpyrrolidine (NMPD) was developed. The yield of NMPD reached 89.41% under the optimal reaction conditions, and the best catalyst proportion was found to be Pt/V = 1:0.5 on HAP. The catalysts exhibited excellent stability, with a yield of 85.21% even after running for 100 hours.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Organic
Victor Adebomi, Yuwen Wang, Mahesh Sriram, Monika Raj
Summary: The site-selective reaction at a specific C-N amide bond is a challenging task. By using twisted amides and electronic activation, a particular amide bond can be selectively activated for C-C bond formation even in the presence of similar amides.
Article
Chemistry, Multidisciplinary
Sebastian Heindl, Margaux Riomet, Jan Matyasovsky, Miran Lemmerer, Nicolas Malzer, Nuno Maulide
Summary: A chemoselective and robust protocol for the gamma-oxidation of beta,gamma-unsaturated amides has been developed, showcasing the synthetic utility of the products obtained through radical cyclisation reactions and oxidation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Min Tao, Jiasheng Qian, Zuanguang Chen, Lin-Kun An, David M. Wilson, Jianbo Liu
Summary: We report the one-pot synthesis of N-CF3 heteroaryl amides from heteroaryl carboxylic acids and sterically hindered isothiocyanates, including various amino acid analogues, in the presence of AgF. This method represents a complementary approach to our previous work and allows modification of previously inaccessible structures, including alpha-tertiary amines and N-CF3-modified pharmaceuticals.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yu Tang, Rebecca L. Grange, Oliver D. Engl, Scott J. Miller
Summary: This article reports a simple and efficient chemoselective acylation method for nucleosides and nucleotides, which allows for the synthesis of O-acylated or N-acylated products with excellent chemoselectivity using mild reaction conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Simone Ghinato, Davide Territo, Andrea Maranzana, Vito Capriati, Marco Blangetti, Cristina Prandi
Summary: The nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides with organolithium reagents in cyclopentyl methyl ether proceeds efficiently, providing ketones with up to 93% yield while effectively suppressing over-addition reactions. The methodology allows for straightforward synthesis of ketones under aerobic conditions without the need for pre-activated amides. The study demonstrates a paradigm shift in the reactivity of carboxylic acid amides with organolithiums.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Lucio Minuti, Francesca Piazzolla, Andrea Temperini
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Andrea Temperini, Francesca Piazzolla, Lucio Minuti, Massimo Curini, Carlo Siciliano
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Andrea Temperini, Lucio Minuti, Tommaso Morini, Ornelio Rosati, Francesca Piazzolla
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)