Article
Chemistry, Organic
Zheng-Yang Gu, Hui Han, Zi-Yin Li, Shun-Jun Ji, Ji-Bao Xia
Summary: This method utilizes amines, isocyanides, and diazo compounds as carbene sources to provide a synthetic simple and highly efficient strategy for the straightforward synthesis of functionalized amidines with a range of substrates.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Linlin Ding, Yue Zhao, Hongjian Lu, Zhuangzhi Shi, Minyan Wang
Summary: For the first time, a catalytic enantioselective propargyl-aryl cross-coupling between two electrophiles was achieved in a stereoconvergent manner. The potential utility of this conversion is demonstrated in the facile construction of stereoenriched bioactive molecule derivatives and medicinal compounds based on the diversity of acetylenic chemistry. Detailed experimental studies have revealed the key mechanistic features of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Thermodynamics
David E. Couch, Goutham Kukkadapu, Angie J. Zhang, Ahren W. Jasper, Craig A. Taatjes, Nils Hansen
Summary: This study investigates the radical-radical reaction of phenyl (C6H5) and propargyl (C3H3) and finds that the propargyl radical reaction can contribute to the formation of polycyclic radicals related to soot inception. By conducting experiments and simulations, it is observed that the radical concentration is positively correlated with temperature under the conditions of 800-1600 K and 25 Torr pressure, and eliminating the radical reactions leads to a discrepancy between simulation and experiment.
PROCEEDINGS OF THE COMBUSTION INSTITUTE
(2023)
Article
Thermodynamics
Akira Matsugi, Shunsuke Suzuki
Summary: The reaction pathways between propargyl and indenyl radicals, leading to the formation of acenaphthylene, were investigated. Quantum chemical methods were used to explore the potential energy surfaces for the reactions. Several reaction pathways for the formation of tricyclic species, which eventually produce acenaphthylene, were identified. The results indicate that acenaphthylene can be formed via three different routes, depending mainly on temperature. A simplified reaction mechanism for the major reaction pathways is proposed for kinetic modeling.
COMBUSTION AND FLAME
(2024)
Article
Chemistry, Applied
Alisa S. Sunagatullina, Ferdinand H. Lutter, Konstantin Karaghiosoff, Paul Knochel
Summary: We have developed a new iron-catalyzed reaction for converting alkyl iodides into alkylzinc iodides. The reaction exhibits diastereoselective ring closures when a remote double bond is present at position 5. Furthermore, the resulting zinc reagents can be further reacted with various electrophiles under copper or palladium catalysis to provide diverse polyfunctional products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Alisa S. Sunagatullina, Ferdinand H. Lutter, Paul Knochel
Summary: In this study, various dialkylmagnesiums were synthesized by reacting primary or secondary alkyl iodides with sBu(2)Mg, and these reagents underwent diverse reactions with different compounds to yield stereodefined products. Mechanistic studies revealed that these reactions proceed via a radical pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Endong Wang, Junxia Ding
Summary: In certain fuel flames, i-C4H5 radical and C3H3 radical can coexist in appreciable concentrations, but the detailed reaction mechanism leading to aromatic rings is still not fully explored. This study carefully constructed a reaction network at the CBS-QB3 level of theory, proposing multiple possible reaction paths including cyclization, ring expanse, and isomerization reactions that lead to the formation of aromatic rings such as toluene. This work should be valuable for further studies in constructing kinetic mechanisms in the field of combustion.
CHEMICAL PHYSICS LETTERS
(2021)
Article
Chemistry, Physical
Nureshan Dias, Ranil M. Gurusinghe, Arthur G. Suits
Summary: Chirped-pulse rotational spectroscopy was used to investigate a multichannel radical-radical reaction of relevance to planetary atmospheres and combustion. The reaction of NO + propargyl yielded six product channels containing eight detected species.
JOURNAL OF PHYSICAL CHEMISTRY A
(2022)
Article
Chemistry, Applied
Lyudmila A. Grishchenko, Lidiya N. Parshina, Lyudmila I. Larina, Yana A. Kostyro, Boris A. Trofimov
Summary: New salicylate derivatives of arabinogalactan have been synthesized with high yield, showing high anti-coagulation activity. The reaction yield varies depending on the base used, and unexpected additional reactions were observed in the presence of piperidine.
CARBOHYDRATE POLYMERS
(2021)
Article
Chemistry, Multidisciplinary
Jiaxin Liu, Yin Wei, Min Shi
Summary: This study reveals the reaction mechanisms of two consecutive visible light photo-induced chain processes, triggered by photo-induced single-electron transfer and direct SET processes respectively. These processes were supported by mechanistic studies and experiments to achieve a redox-neutral outcome.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Benxiang Zhang, Jiayan He, Yi Li, Tao Song, Yewen Fang, Chaozhong Li
Summary: Acylphosphonates with the 5,5-dimethyl-1,3,2-dioxophosphinanyl skeleton have been developed as efficient intermolecular radical acylation reagents for cobalt-catalyzed Markovnikov hydroacylation of unactivated alkenes at room temperature. The protocol shows broad substrate scope and good functional group compatibility, providing satisfactory yields of branched ketones. The proposed mechanism involves Co-H mediated hydrogen atom transfer and subsequent trapping of alkyl radicals by acylphosphonates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Wande Zhang, Shiqiang Wei, Jingping Qu, Baomin Wang
Summary: The TsOH-catalyzed allenylation of pyrazolones with propargylic alcohols has been developed, showing good tolerance towards a wide range of substrates and offering ease of operation, scalability, and high yield. The integration of pharmaceutical-related pyrazolone skeleton and the allenyl group into a single molecule not only enriches structural diversity but also potentially broadens biological activity. The synthesis of compound 3aa in gram-scale with maintained yield and efficiency highlights the practical application potential of this process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Physical
Xiaochong Guo, Zhaoxin Shi, Feng-Hua Zhang, Zhaobin Wang
Summary: We developed a calcium-catalyzed asymmetric reductive coupling reaction, which can efficiently synthesize valuable chiral tertiary alcohols with vicinal stereocenters by reacting propargylic chlorides and ketones. These reactions proceed in a radical-polar crossover manner under mild conditions, with good regio-, diastereo-, and enantioselectivity control.
Article
Chemistry, Multidisciplinary
Yongsuk Jung, Seok Yeol Yoo, Yonghoon Jin, Jaehyun You, Seungcheol Han, Jeongwoo Yu, Yoonsu Park, Seung Hwan Cho
Summary: In this study, a highly selective allyl-allyl coupling reaction between branched allyl alcohols and alpha-silyl-substituted allylboronate esters was reported, catalyzed by a chiral iridium complex. By permuting the chiral iridium catalysts and the substrates, all four stereoisomers bearing two consecutive chiral centers were efficiently obtained. Mechanistic studies revealed the origins of the diastereo- and chemoselectivities, and additional synthetic modifications for preparing enantioenriched compounds containing contiguous chiral centers were also included.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Ryan K. Spencer, James S. Nowick
ISRAEL JOURNAL OF CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Ryan K. Spencer, Adam G. Kreutzer, Patrick J. Salveson, Hao Li, James S. Nowick
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Biochemistry & Molecular Biology
Ryan K. Spencer, Allon I. Hochbaum
Article
Chemistry, Physical
Jeffrey B. Kortright, Jing Sun, Ryan K. Spencer, Xi Jiang, Ronald N. Zuckermann
JOURNAL OF PHYSICAL CHEMISTRY B
(2017)
Article
Chemistry, Organic
Ryan Spencer, Kevin H. Chen, Gerald Manuel, James S. Nowick
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Gagik G. Melikyan, Ryan Spencer, Edwin Abedi
JOURNAL OF ORGANIC CHEMISTRY
(2009)
Article
Chemistry, Multidisciplinary
Ryan K. Spencer, Hao Li, James S. Nowick
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Inorganic & Nuclear
Gagik G. Melikyan, Ruth Sepanian, Ryan Spencer, Aaron Rowe, Pogban Toure
Article
Chemistry, Inorganic & Nuclear
Gagik G. Melikyan, Ryan Spencer, Aaron Rowe
Article
Chemistry, Organic
Gagik G. Melikyan, Erin Voorhees, Christopher Wild, Ryan Spencer, Justin Molnar
TETRAHEDRON LETTERS
(2010)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
