Article
Polymer Science
Bruno Grignard, Pieter Mampuys, Julien Escudero, Dario Masullo, Filip Lemiere, Bert U. W. Maes, Christophe Detrembleur
Summary: This study investigates the catalyst-free synthesis of urethanes from masked isocyanates and soft nucleophiles. The method achieves high functional group tolerance and has been successfully applied to construct regioregular functional polyurethanes.
Article
Chemistry, Multidisciplinary
Lingjian Zi, Jing Zhang
Summary: We describe a method for iron-catalyzed amide bond formation using readily available carboxylic acids and isocyanates. This method utilizes an abundant and biocompatible iron catalyst and accessible starting materials, generates only CO2 as a byproduct, and has a broad substrate scope with good functional group compatibility. Therefore, it provides a cost-effective and practical protocol to access a diverse variety of amides.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Applied
Paola Acosta-Guzman, Andrea Ojeda-Porras, Diego Gamba-Sanchez
Summary: The construction of amide bonds is of great interest due to their prevalence in bioactive molecules. This review presents the most viable strategies for constructing amide bonds, with a focus on recent developments in the field.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yiping Li, Jingyue Li, Guangjun Bao, Changjun Yu, Yuyang Liu, Zeyuan He, Peng Wang, Wen Ma, Junqiu Xie, Wangsheng Sun, Rui Wang
Summary: In this study, a novel coupling reagent NDTP was explored, which exhibited mild, nonirritating, convenient availability, and recyclability. It could activate carboxylic acids via acyl thiocyanide and enable the rapid synthesis of amides and peptides under mild conditions. Furthermore, the methodology was compatible with Fmoc-SPPS, providing an alternative approach for peptide manufacturing.
Article
Chemistry, Organic
Eleonora Tosi, Jean-Marc Campagne, Renata Marcia de Figueiredo
Summary: A copper(II)/HOBt-catalyzed microwave-assisted synthesis method for dipeptides and general amides has been developed. Instead of traditional carboxylic acid activation, the method utilizes N-acyl imidazoles as activated amino partners, providing a nonconventional approach for the synthesis of dipeptides and amides through the less studied N-* C direction. The method has been successfully applied in the synthesis of various dipeptides and amides on a gram-scale, and the mild reaction conditions allow for coupling reactions with sensitive amino acids without racemization. Experimental observations have led to the proposal of a plausible reaction pathway for the couplings.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Michael Winn, Michael Rowlinson, Fanghua Wang, Luis Bering, Daniel Francis, Colin Levy, Jason Micklefield
Summary: Coronatine and related bacterial phytotoxins mimic plant hormone JA-Ile and disrupt important plant physiological signaling pathways. The enzyme CfaL can synthesize JA-Ile and a variety of amides, showing potential for applications in agrochemicals and pharmaceuticals.
Article
Chemistry, Organic
Christopher R. Opie, Hidetoshi Noda, Masakatsu Shibasaki, Naoya Kumagai
Summary: This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.
Article
Chemistry, Multidisciplinary
Aiping Wang, Ya Xie, Jingjing Wang, Da Shi, Han Yu
Summary: An efficient and economical amidation strategy using a polyoxometalate-based iron catalyst has been developed, resulting in good yields of corresponding amide products for aliphatic, aromatic, and heterocyclic substrates without the need for additional base or organic ligands. Most significantly, the study presents the first example of heterogeneous iron (III)-catalyzed formation of diamides.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Rabindranath Lo, Martin Pykal, Andreas Schneemann, Radek Zboril, Roland A. Fischer, Kolleboyina Jayaramulu, Michal Otyepka
Summary: Covalent hybrids of graphene and metal-organic frameworks (MOFs) have great potential in various technologies, especially catalysis and energy applications, due to their combination of conductivity and porosity. The formation of an amide bond between carboxylate-functionalized graphene acid (GA) and amine-functionalized UiO-66-NH2 MOF is an efficient strategy for creating such hybrids. This study used density functional theory (DFT) calculations to elucidate the mechanism of amide bond formation between GA and UiO-66-NH2, highlighting the crucial role of zirconium within UiO-66 as a catalyst. Insight into the binding interactions between graphene derivatives and MOFs can lead to tailored synthesis strategies for these nanocomposite materials.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Inorganic & Nuclear
Isabel Abanades Lazaro, Ross S. Forgan, Francisco. G. Cirujano
Summary: The influence of composition and textural characteristics of ultra-small isoreticular UiO-type metal-organic frameworks (MOFs) on catalytic performance is evaluated in this study. The activity of Zr-MOF nanoparticles is tested using two different amide bond formation reactions as proof-of-concept. The results provide insights into the catalytic mechanism and optimal properties for enhancing performance.
DALTON TRANSACTIONS
(2022)
Review
Chemistry, Multidisciplinary
Wataru Muramatsu, Tomohiro Hattori, Hisashi Yamamoto
Summary: The article discusses the development of methods for amide bond formation without typical condensation reagents, presenting a metal-templated macrolactamisation approach that addresses long-standing challenges in peptide chemistry through substrate control.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Max Lubberink, William Finnigan, Sabine L. Flitsch
Summary: Amide bonds are commonly formed in the pharmaceutical industry and there is a growing interest in biocatalytic methods for their synthesis. The use of low water systems and ATP-dependent enzymes have shown promise in driving amide bond formation. A publicly available database, RetroBioCat, has been compiled to provide literature on these methods.
Article
Chemistry, Organic
Kenji Yamashita, Yuki Fujiwara, Yoshitaka Hamashima
Summary: We describe an efficient method for benzylic C-H fluorination via sequential hydrogen-atom transfer (HAT) and oxidative radical-polar crossover utilizing the Ag(I)/Selectfluor system. Amide ligands, such as benzamide and sulfonamide, substantially facilitate the processes leading to a carbocation intermediate, which subsequently reacts with nucleophilic fluorinating reagent to form a C-F bond. This protocol is applicable to the fluorination of all 1 degrees, 2 degrees, and 3 degrees C-H bonds as well as to late-stage C-H fluorination of bioactive molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Devaneyan Joseph, Sunwoo Lee
Summary: Amides can react with NaN3 to form acyl azides, which can further react to produce symmetrical ureas via acyl substitution and Curtius rearrangement at different temperatures. Secondary amides can also produce acyl azides through sequential reactions with p-toluenesulfonyl chloride and NaN3. Additionally, keto-stabilized iminophosphoranes can be prepared from a one-pot reaction of amides, NaN3, and phosphines.
Correction
Chemistry, Multidisciplinary
Michael S. Christodoulou, Martina Letizia Contente, Sabrina Dallavalle, Andrea Pinto
Summary: This study reports an enzymatic amide bond formation method using Mycobacterium smegmatis acyltransferase for synthesis of aminooxo-acids.
Article
Chemistry, Medicinal
Ryota Saito, Saori Suzuki, Kaname Sasaki
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2016)
Article
Chemistry, Multidisciplinary
Yusuke Hashimoto, Saki Tanikawa, Ryota Saito, Kaname Sasaki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Organic
Toru Hatanaka, Ryosuke Yuki, Ryota Saito, Kaname Sasaki
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Ryota Saito, Moe Tamura, Saya Kawano, Yutaka Yoshikawa, Akihiro Kato, Kaname Sasaki, Hiroyuki Yasui
NEW JOURNAL OF CHEMISTRY
(2017)
Article
Chemistry, Organic
Kaname Sasaki, Yusuke Hashimoto
Article
Biochemistry & Molecular Biology
Kazumitsu Onizuka, Akira Usami, Yudai Yamaoki, Tomohito Kobayashi, Madoka E. Hazemi, Tomoko Chikuni, Norihiro Sato, Kaname Sasaki, Masato Katahira, Fumi Nagatsugi
NUCLEIC ACIDS RESEARCH
(2018)
Article
Chemistry, Organic
Kazuki Tohda, Masashi Saito, Hiroaki Sakai, Daisuke Ishikura, Ryota Saito, Kaname Sasaki
Article
Chemistry, Organic
Kaname Sasaki, Kazuki Tohda
TETRAHEDRON LETTERS
(2018)
Article
Biochemistry & Molecular Biology
Reda Mhidia, Emmanuelle Boll, Fabien Fecourt, Mikhail Ermolenko, Nathalie Ollivier, Kaname Sasaki, David Crich, Bernard Delpech, Oleg Melnyk
BIOORGANIC & MEDICINAL CHEMISTRY
(2013)
Article
Chemistry, Multidisciplinary
Shunichi Kusumi, Satoshi Tomono, Shunsuke Okuzawa, Erika Kaneko, Takashi Ueda, Kaname Sasaki, Daisuke Takahashi, Kazunobu Toshima
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Organic
Sylvain Aubry, Kaname Sasaki, Laure Eloy, Genevieve Aubert, Pascal Retailleau, Thierry Cresteil, David Crich
ORGANIC & BIOMOLECULAR CHEMISTRY
(2011)
Article
Chemistry, Inorganic & Nuclear
Kaname Sasaki, Sylvain Aubry, David Crich
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2011)
Article
Chemistry, Organic
Saya Kawano, Yutaka Yoshikawa, Akihiro Kato, Shoko Higashi, Kyohei Mitani, Hiroyuki Yasui, Yoichi Habata, Shunsuke Kuwahara, Kaname Sasaki, Ryota Saito
TETRAHEDRON LETTERS
(2019)
Review
Biochemistry & Molecular Biology
Kaname Sasaki, Ren Isoda
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY
(2020)
