Article
Chemistry, Multidisciplinary
An Liu, Chuanfa Ni, Qiqiang Xie, Jinbo Hu
Summary: A protocol has been developed for the modular assembly of the alpha-fluoroamide motif, allowing for the efficient synthesis of diverse alpha-fluoroamides from readily available aldehydes and tertiary amines through a three-component fluorination-aminocarbonylation process. The success of the process relies on the unique difluorocarbene reagent TMSCF2Br, with the mechanism involving 1,2-fluorine and oxygen migrations of the in situ formed intermediates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chenwei Liu, Tongshun An, Weiheng Yuan, Huiying Dai, Xiaolan Liang, Zhiping Yin
Summary: In this study, a practical palladium-catalysed double carbonylation reaction was developed for the construction of various N-aryl phthalimides by reacting nitro compounds with o-dihaloarenes. The success of this transformation relied on the use of Mo(CO)(6) as both a reducing agent and a solid carbonyl source.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Youcan Zhang, Hui-Qing Geng, Xiao-Feng Wu
Summary: The study presents a palladium-catalyzed four-component perfluoroalkylation/aminocarbonylation reaction, successfully synthesizing various β-perfluoroalkyl amides. The reaction system shows good compatibility with a wide range of substrates, including anilines, alkylamines, and demonstrates good functional-group tolerance and excellent chemoselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xing-Feng Pan, Xuanzhang Bao, Ren-Rui Xu, Xinxin Qi, Xiao-Feng Wu
Summary: A straightforward and efficient method for the synthesis of carbamoyl-substituted oxindoles was developed using a palladium-catalyzed Heck cyclization and reductive aminocarbonylation reaction. This reaction demonstrated good compatibility with various functional groups, tolerating both nitroarenes and nitroalkanes. Employing Mo(CO)(6) as a solid CO source, a wide range of carbamoyl-substituted oxindoles were obtained in moderate to high yields without the need for external reductants.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yun Kang, Jin-Liang Lu, Zhi Zhang, Ying-Kang Liang, Ai-Jun Ma, Jin-Bao Peng
Summary: A palladium-catalyzed intramolecular Heck/aminocarbonylation of alkene-tethered iodobenzenes with nitro compounds has been developed for the synthesis of carbamoyl-substituted benzoheterocycles. This procedure utilizes Mo(CO)(6) as a solid CO source, eliminating the need for external reductants or additives. Nitroarenes and nitroalkanes are both well tolerated, resulting in moderate to high yields of carbamoyl-substituted dihydrobenzofurans and indolines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shengdong Wang, Guillaume Force, Jean-Francois Carpentier, Yann Sarazin, Christophe Bour, Vincent Gandon, David Leboeuf
Summary: A modular one-pot synthesis of 9,10-dihydroacridine frameworks was achieved through a reaction sequence involving selective ortho-C alkenylation of diarylamines with aryl alkynes followed by intramolecular hydroarylation. The combination of hexafluoroisopropanol and triflimide as catalysts played a crucial role in triggering the whole process.
Article
Chemistry, Multidisciplinary
Jixin Wang, Donghao Luo, Ying Hu, Zhili Duan, Jianlin Yao, Konstantin Karaghiosoff, Jie Li
Summary: Simultaneous formation of carbon-carbon and carbon-heteroatom bonds through transition metal-catalyzed alkene difunctionalization is a powerful tool for synthetic organic chemistry. A new type of S- and P-stabilized bromoallenes for palladium-catalyzed modular allenation and borylation of alkenes has been developed, enabling the synthesis of multiply functionalized allenes in a highly selective manner. This method offers broad substrate scope and functional group compatibility, allowing for the facile installation of allenyl and boryl groups across alkenes.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Applied
Laura Carceller-Ferrer, Gonzalo Blay, M. Carmen Munoz, Jose R. Pedro, Carlos Vila
Summary: A diastereo- and enantioselective synthesis of spirocyclopropylpyrazolones was achieved through a Michael/alkylation cascade reaction of 4-arylidenepyrazol-5-ones with diethyl 2-bromomalonate catalyzed by (DHQ)(2)AQN. The corresponding spirocyclic compounds were obtained selectively with yields of 30-83%, diastereoselectivities ranging from 60:40 to >95:5, and enantiomeric excess of 26-93% under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Khadijah Anwar, Francisco Jose Aguilar Troyano, Ayham H. Abazid, Oumayma El Yarroudi, Ignacio Funes-Ardoiz, Adrian Gomez-Suarez
Summary: Here, we present a highly modular strategy for synthesizing spirocyclic scaffolds from easily available starting materials, such as cyclic ketones and alpha-amino or oxamic acids. The reaction involves a simple Knoevenagel condensation, followed by a cascade Giese-type reaction and base-mediated cyclization, resulting in a wide range of polar spirocyclic products in high yields. Our method allows for easy diversification of the products, thus providing rapid access to libraries of potential drug-like molecules.
Article
Chemistry, Organic
Tomas Carny, Peter Kisszekelyi, Martin Markovic, Tibor Gracza, Peter Koos, Radovan Sebesta
Summary: Here, we present the development of mechanochemical amino- and oxycarbonylation reactions using FeBr2(CO)(4) as a solid CO source. This Pd/XantPhos-catalyzed reaction enables the synthesis of a wide range of carboxamides and esters from aryl iodides and various amines or phenols. Notably, both primary and secondary amines, including amino acids, can be used as N-nucleophiles.
Article
Chemistry, Multidisciplinary
Wenyao Wang, Xiaoze Bao, Shiqiang Wei, Shah Nawaz, Jingping Qu, Baomin Wang
Summary: A catalytic asymmetric sequential annulation/aldol reaction of 4-isothiocyanato pyrazolones and allenyl ketones has been developed, leading to a series of spiro[pyrrole-pyrazolone] heterocycles and structurally novel spiro[thiopyranopyrrole-pyrazolone] derivatives in good yields with high to excellent enantioselectivities. The diversity of product structures was further enhanced by easy transformations.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Depeng Duan, Lu Song
Summary: The decarboxylative cross-coupling of oxamic acids with (hetero)aryl halides was achieved through the synergistic merger of organic photoredox with nickel catalysis. This new amide synthesis protocol is mild, operationally simple, and can transform a wide range of oxamic acids into the corresponding carbamides in good to excellent yields. It is also scalable and can be used for late-stage modification of complex molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Liwen Liu, Yu Liu, Xue Shen, Xiao Zhang, Shengqi Deng, Yang Chen
Summary: A simple, mild, catalyst-free, and efficient reductive cyanation reaction of tertiary amides mediated by (KOBu)-Bu-t under hydrosilylation conditions has been reported. A series of alpha-aminonitriles are obtained in moderate to high yields with good tolerance towards various functional groups. The reaction utilizes readily available amide substrates, a cheap and versatile base (KOBu)-Bu-t, and a commercially available hydrosilane (EtO)(3)SiH, and is convenient for workup and purification.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Li-Miao Yang, Shan-Shan Li, You-Ya Zhang, Jin-Liang Lu, Jing-Tong Deng, Ai-Jun Ma, Xiang-Zhi Zhang, Shu-Yu Zhang, Jin-Bao Peng
Summary: A palladium-catalyzed reductive aminocarbonylation reaction is developed for the synthesis of phenylacetamides from benzylic ammonium triflates and nitroarenes. This method tolerates a variety of alkyl, aryl, and halide substituents on both substrates, allowing for the preparation of different substituted phenylacetamides in moderate to good yields.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Xianda Wu, Minghong Chen, Shuiyun Zheng, Jie Wu, Gang Liu, Fu-Sheng He
Summary: This study presents an efficient approach to synthesizing sulfonyl-containing phosphorothioates by merging photoredox and copper catalysis at room temperature. The method is compatible with a wide range of substrates and can be applied to the late-stage modification of complex molecules.
Article
Chemistry, Multidisciplinary
Amanda Bongers, Patrick J. Moon, Andre M. Beauchemin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Jean-Francois Vincent-Rocan, Christian Clavette, Kyle Leckett, Andre M. Beauchemin
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Article
Chemistry, Organic
Amanda Bongers, Indee Ranasinghe, Philippe Lemire, Alyssa Perozzo, Jean-Francois Vincent-Rocan, Andre M. Beauchemin
Article
Chemistry, Organic
Amanda Bongers, Christian Clavette, Wei Gan, Serge I. Gorelsky, Lyanne Betit, Kaitlyn Lavergne, Thomas Markiewicz, Patrick J. Moon, Nicolas Das Neves, Nimrat K. Obhi, Amy B. Toderian, Andre M. Beauchemin
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Xiao-Qiang Hu, Jia-Rong Chen, Qiang Wei, Feng-Lei Liu, Qiao-Hui Deng, Andre M. Beauchemin, Wen-Jing Xiao
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Sheng-Ying Hsieh, Benedikt Wanner, Philip Wheeler, Andre M. Beauchemin, Tomislav Rovis, Jeffrey W. Bode
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Organic
Nicolas Das Neves, Michael Raymond, Andre M. Beauchemin
Article
Chemistry, Multidisciplinary
Amanda Bongers
Summary: Research poster sessions are an excellent example of how scientists rely not only on technical skills but also on interpersonal interactions, communication, and other behaviors learned from participating in social environments.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Article
Chemistry, Multidisciplinary
Yu Pei, Sarah Gulycz, Zhe She, Amanda Bongers
Summary: We implemented a scaffolded assessment activity in a remote analytical chemistry class to introduce students to chromatography theories and principles. The activity involved analyzing chromatograms, interpreting data, and defining chromatographic terms to solve multistep calculations. We found that this scaffolded design helped students develop process skills for problem-solving in analytical chemistry.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Chemistry, Multidisciplinary
Alexandria Parker, Evan Noronha, Amanda Bongers
Summary: The importance of sustainability and green chemistry teachings in response to global environmental issues is emphasized, but these topics are not well-integrated into most post-secondary organic chemistry lecture courses. To address this issue, a study was conducted to investigate the barriers faced by organic chemistry educators in incorporating green and sustainable chemistry into their courses. Interviews with 8 faculty members in Canadian universities were analyzed qualitatively, and major themes related to content, structure, resources, management, and individuals were identified. The findings will inform curriculum development and the creation of open educational resources for organic chemistry.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Chemistry, Multidisciplinary
Alexandria Parker, Evan Noronha, Amanda Bongers
Summary: The rise of global environmental issues has highlighted the importance of sustainability and green chemistry teachings. However, these topics are often neglected in post-secondary organic chemistry lecture courses. This article investigates the barriers to integrating green and sustainable chemistry into organic chemistry classrooms in Canadian universities and explores the knowledge, relevance, and resources available to organic chemistry educators for implementing change. The findings will inform curriculum development and the creation of open educational resources for organic chemistry.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Education & Educational Research
Amanda Bongers, Berthorie Beauvoir, Nicholas Streja, Georg Northoff, Alison B. Flynn
CHEMISTRY EDUCATION RESEARCH AND PRACTICE
(2020)
Article
Education & Educational Research
Amanda Bongers, Georg Northoff, Alison B. Flynn
CHEMISTRY EDUCATION RESEARCH AND PRACTICE
(2019)
