Article
Chemistry, Organic
Jia-Le Zheng, Fei Liu, Xue Song, Zhi Zhao, Wei Du, Ying-Chun Chen
Summary: In this study, we found that dienones generated from the Morita-Baylis-Hillman carbonates of 2-cyclopentenone under Pd(0) catalysis could be umpolunged through pi-Lewis base activation to form regioselective eta 2-Pd(0) complexes, which then underwent asymmetric inverse-electron-demand oxa-Diels-Alder reaction with alpha-cyano chalcones. This study successfully constructed a range of fused pyran frameworks with dense substitutions and demonstrated excellent stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Arturs Sperga, Renate Melngaile, Armands Kazia, Sergey Belyakov, Janis Veliks
Summary: The investigation into the properties and reactivity of fluoromethylsulfonium salts led to the redesign of reagents for fluoromethylene transfer chemistry, resulting in more efficient synthesis of a range of monofluorinated cyclopropane derivatives. The new reagents, with increased reactivity from halide incorporation and improved balance between reactivity and crystallinity from 2,4-dimethyl substitution, demonstrated utility in a fluorocyclopropanation protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jie Li, Xinhui Zhang, Yisen Yao, Yapei Gao, Wen Yang, Wanxiang Zhao
Summary: An efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reaction has been developed for the synthesis of oxygen atom-substituted allylboronates with aryl/vinyl bromides, iodides, and triflates. This protocol offers a broad substrate scope, excellent functional group tolerance, and easy gram-scale preparation, providing an alternative approach for the synthesis of allylic alcohols and their derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jie Wang, Xiaotian Qi, Xiao-Long Min, Wenbin Yi, Peng Liu, Ying He
Summary: This study presents a novel approach for the synthesis of axially chiral styrenes through tandem iridium catalysis. The method allows for efficient and selective preparation of chiral ligands needed for asymmetric synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Chun-Tai Hung, Chun-Wei Lu, Shi-Han Huang, Yin-Feng Lu, Hsiang-Chi Chou, Cheng-Che Tsai
Summary: This research utilizes chiral sulfinamides as nucleophiles in intramolecular allylic substitution and sequential aerobic oxidation with aza-Michael addition reactions, achieving good yields of chiral isoindolines and high diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Renren Li, Haocheng Zhang, Bangkui Yu, Hanmin Huang
Summary: A novel palladium-catalyzed cascade annulative aminomethylamination of diene-tethered enynes with aminals is reported. This method allows for the efficient synthesis of functionalized benzofulvenes with excellent chemo- and regioselectivities, as well as high atom economy. Mechanistic studies reveal the preferential reaction of alkylpalladium species with 1,3-enyne over 1,3-diene in initiating the cyclizative aminomethylamination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jianguo Yang, Saimei Liu, Jing Gui, Daokai Xiong, Jinshan Li, Zhiming Wang, Jun Ren
Summary: A highly selective hydroxyalkylation of aniline derivatives with arylglyoxal hydrates has been achieved using HFIP as a catalyst. The reaction provides efficient synthesis of various N,N-dialkylanilines and their derivatives with alpha-hydroxy carbonyl units under mild conditions. The method has shown great synthetic potential by enabling the facile synthesis of several structurally interesting molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Travis Menard, Aragorn Laverny, Scott E. Denmark
Summary: This method describes the catalytic, enantioselective carbosulfenylation of alkenes to construct difficult-to-generate, enantioenriched, 3,4-disubstituted chromans with moderate to high yields and excellent enantioselectivities. The resulting thioether moiety is amenable to various functional group manipulations and transformations, providing access to sulfur-containing functional groups present in natural products and pharmaceuticals.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ming Yu Jin, Yali Zhou, Dengmengfei Xiao, Yipeng You, Qianqian Zhen, Guanyu Tao, Peiyuan Yu, Xiangyou Xing
Summary: The mechanistic uniqueness and versatility of borrowing hydrogen catalysis provides an opportunity to investigate the controllability of a cascade reaction, and more importantly, to realize either one or both of chiral recognition and chiral induction simultaneously. In this study, using a robust Ru-catalyst, both kinetic resolution and asymmetric induction were achieved with remarkable levels of efficiency and enantioselectivity, showing the importance of catalyst-substrate pi-pi interactions in realizing stereochemical diversity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhicong Lin, Boxiang Liu, Yu Wang, Siju Li, Shifa Zhu
Summary: Under nickel catalysis, acetylene reacts with aldehyde to form a 5-membered oxa-metallacycle, which is then converted to vinyl-substituted alcohols via a silane-mediated sigma-bond metathesis and subsequent reductive elimination. This methodology offers mild conditions, good functional group tolerance, and a wide range of substrates.
Article
Chemistry, Organic
Liangzhen Hu, Tianyong Gao, Qingfu Deng, Yan Xiong
Summary: A new method for the hydroxylation of allylic alcohols using [hydroxyl(tosyloxy)iodo]benzene (HTIB) as both oxidant and reagent has been developed, along with the enantioselective alkyoxylation as well as hydroxylation catalyzed by simple chiral iodine benzene through the in situ hypervalent iodine synthesis strategy.
Article
Chemistry, Inorganic & Nuclear
Ilya A. Bezkishko, Almaz A. Zagidullin, Mikhail N. Khrizanforov, Tatiana P. Gerasimova, Kamil A. Ivshin, Olga N. Kataeva, Yulia S. Ganushevich, Vasili A. Miluykov, Peter Loennecke, Evamarie Hey-Hawkins
Summary: A series of 3,4,5-triaryl-1,2-diphosphaferrocenes were synthesized and their structures and electrochemical properties were investigated. The results showed that these complexes exhibit good stability of the oxidized form.
INORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Rodney A. Fernandes, Naveen Chandra, Ashvin J. Gangani, Gulenur N. Khatun
Summary: An efficient method for the synthesis of (E)-(3-alkoxybut-1-enyl)benzenes has been developed via Pd-catalyzed regioselective intermolecular hydroalkoxylation of 1-arylbutadienes. This method offers a simple operation, without the need for dry reaction conditions, and shows good tolerance to various substrates. The presence of chloromethyl methyl ether (MOMCl) as an additive is crucial to the success of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Christian A. M. R. van Slagmaat, Jurrie Noordijk, Luciano G. Monsegue, Siri Mogensen, Darya Hadavi, Peiliang Han, Peter J. L. M. Quaedflieg, Gerard K. M. Verzijl, Paul L. Alsters, Stefaan M. A. De Wildeman
Summary: A novel and green route for the synthesis of cyclopentane-1,3-diamine (CPDA) from hemicellulosic feed-stock was established, involving a multi-step synthesis process. The CPDA derivatives were further reacted with bio-based lactones and HMF to synthesize bifunctional diol monomers, with one monomer successfully applied in the synthesis of polyurethanes.
Review
Chemistry, Multidisciplinary
Junhua Li, Yian Shi
Summary: This review provides a brief summary of the development of asymmetric hydroesterification, hydrocarboxylation, and hydroamidation with CO and its surrogates, which offer an effective and straightforward approach to optically active carboxylic acids and their derivatives.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Organic
Jakob F. Schneider, Florian C. Falk, Roland Froehlich, Jan Paradies
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2010)
Review
Chemistry, Multidisciplinary
Jakob F. Schneider, Roland Froehlich, Jan Paradies
ISRAEL JOURNAL OF CHEMISTRY
(2012)
Article
Chemistry, Organic
Jakob F. Schneider, Roland Froehlich, Jan Paradies
SYNTHESIS-STUTTGART
(2010)
Article
Chemistry, Applied
Jakob F. Schneider, Adam Becalski, Tony Zhao, Fuqi Chen, Yifu Liao, Dorothea F. K. Rawn
Summary: 2- and 3-monochloropropanediol esters (MCPDEs) are process-induced contaminants found in vegetable oils used for food production. In this study, infant formula samples from the Canadian market were analyzed in 2015 and 2019, showing a decrease in MCPDE levels over time. The occurrence of MCPDEs in infant formula has been a concern, but the data suggests that levels have been decreasing.
FOOD ADDITIVES AND CONTAMINANTS PART A-CHEMISTRY ANALYSIS CONTROL EXPOSURE & RISK ASSESSMENT
(2022)
Article
Chemistry, Applied
Jakob F. Schneider, Adam Becalski, Tony Zhao, Yihui Liu, Fuqi Chen, Dorothea F. K. Rawn
Summary: Glycidyl fatty acid esters (GEs) are contaminants in vegetable oils that can release carcinogenic and genotoxic glycidol when hydrolyzed in the human body. The presence of GEs in vegetable oils used for infant formula may pose health risks for babies. A study analyzed different types of infant formula products in 2015 (35 samples) and 2019 (33 samples), finding that the concentrations of bound glycidol reached a maximum of 40.3 ng/g in 2015 samples and 31.5 ng/g in 2019 samples. However, the concentrations of bound glycidol were lower in 2019 compared to previous studies. The study also compared the GE concentrations across different manufacturers.
FOOD ADDITIVES AND CONTAMINANTS PART A-CHEMISTRY ANALYSIS CONTROL EXPOSURE & RISK ASSESSMENT
(2023)
Article
Chemistry, Inorganic & Nuclear
Qinglin Zheng, Jakob F. Schneider, Hashem Amini, Frank Hampel, John A. Gladysz
DALTON TRANSACTIONS
(2019)
