Article
Chemistry, Multidisciplinary
Bec J. Roldan, Travis A. Hammerstad, Matthew S. Galliher, Mitchell H. Keylor, Derek A. Pratt, Corey R. J. Stephenson
Summary: A simple method for accessing trans-2,3-diaryl dihydrobenzofurans is described in this article. The method takes advantage of the equilibrium between quinone methide dimers and their persistent radicals. Phenols are used to disrupt this equilibrium and generate transient phenoxyl radicals, allowing for cross-coupling between the persistent and transient radicals. The resulting quinone methides with pendant phenols rapidly cyclize to form dihydrobenzofurans (DHBs), providing a biomimetic approach for the synthesis of resveratrol-based natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Akanksha Kumari, Anshul Jain, Khyati Shukla, Ranjan Patra, Nirmal K. Rana
Summary: We have developed a highly stereoselective formal [4 + 1] annulation reaction to construct trans-2,3-dihydrobenzofurans using in situ generated supported pyridinium ylide. This approach shows excellent substrate versatility and the capability of gram-scale synthesis. Moreover, the polymer-anchored pyridine can be recovered and reused multiple times. The product has been transformed into valuable molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shuangjing Zhou, Baogui Cai, Chuxia Hu, Xu Cheng, Lei Li, Jun Xuan
Summary: A visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates has been developed, providing a mild and efficient approach for the synthesis of biologically important 2,3-dihydrobenzofuran derivatives in good yields and moderate diastereoselectivities.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Ganesh Shivayogappa Sorabad, Ding-Yah Yang
Summary: A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives is reported. The reaction proceeds through the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins can be easily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Maria Tereza M. Martins, Flaviana Rodrigues F. Dias, Raphael Silva M. de Moraes, Marcos Felipe da Silva, Kaio R. Lucio, Karin D'Oliveira Goes, Patrick A. do Nascimento, Andre S. S. da Silva, Vitor F. Ferreira, Anna C. Cunha
Summary: This article provides an overview of multicomponent reactions (MCRs) that involve ortho-quinone methide intermediates (o-QM) and discusses their applications in organic synthesis and biological processes. QMs are generated through eliminative processes or photochemical reactions and can undergo various types of reactions.
Article
Pharmacology & Pharmacy
Huajie Li, Zhenjie Yu, Haoyi Sun, Bo Liu, Xin Wang, Zhe Shao, Meiling Wang, Weilin Xie, Xingang Yao, Qingqiang Yao, Ying Zhi
Summary: A novel reaction between N-(o-chloromethyl)aryl amides and 3-chlorooxindoles has been reported for the synthesis of a series of 2,3'-spirobi(indolin)- 2'-ones in high yields. Compound 3a was found to change mitochondrial morphology and induce mitophagy pathway, potentially triggering mitophagy in cancer cells.
FRONTIERS IN PHARMACOLOGY
(2022)
Article
Chemistry, Organic
Genhui Chen, Hongjiao Li, Guojuan Liang, Qian Pu, Lijuan Bai, Dexin Zhang, Ying Ye, Yong Li, Jing Zhou, Hui Zhou
Summary: A novel palladium-catalyzed domino reaction was used for the homodimerization of ortho-hydroxyphenyl substituted p-QMs. An interesting palladium-catalyzed intramolecular oxidation reaction was discovered. This method provides an efficient approach for constructing various compounds containing spirocyclohexadienones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Martha C. Mayorquin-Torres, Armando Navarro-Huerta, Mauricio Maldonado-Dominguez, Marcos Flores-Alamo, Braulio Rodriguez-Molina, Martin A. Iglesias-Arteaga
Summary: A series of hybrid dimers with orthogonal steroidal cores bridged by a chroman ketal moiety were obtained through Pd-catalyzed three-component reactions, showing one L-shaped scaffold with large channels. Monte Carlo simulations indicate these voids preferentially allocate n-hexane, suggesting potential applications as selective hosts for small molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Keng-Jia Hsu, Chang-Lin Hsieh, Chi-Jui Tsai, Kien Voon Kong
Summary: In this study, tip-enhanced Raman spectroscopy (TERS) was used to investigate the in situ oxidative generation of Quinone methides (QMs) from alkylphenols facilitated by a transition metal complex. The metal oxidant-mediated transformation of a phenol species and the subsequent oxidative addition reaction of QM were observed and identified based on distinct vibrational features, providing potential for TERS to be established as a chemical detection tool for various QM-mediated reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Organic
Cun Yang, Yanze Li, Qiwen Huang, Xinyao Li
Summary: A mild and efficient synthesis of 3-aryl-2-aminobenzofurans by Lewis acid catalyzed [4+1] cycloaddition of in situ generated o-quinone methides and isocyanides is reported. Compared with the well-known methods, the current reactions are carried out under mild conditions and feature wide substrate scope in high yields at ambient temperature at catalyst loadings as low as 1 mol%.
Article
Chemistry, Organic
Rajat Pandey, Gurdeep Singh, Vinod Gour, Ramasamy Vijaya Anand
Summary: A one-pot approach for the synthesis of 2,3-disubstituted indoles has been developed, providing direct access to a wide range of products in moderate to good yields under mild conditions through base-mediated alkylation and cyclization reactions.
Article
Chemistry, Organic
Meng-Hao Yi, Hai-Shan Jin, Ru-Bing Wang, Li-Ming Zhao
Summary: An efficient copper-catalyzed cascade annulation of o-hydroxyphenyl propargylamines and pyrazolin-5-ones is described, leading to the rapid assembly of a series of valuable pyrano[2,3-c]pyrazoles with good yields across a wide range of substrates in a simple fashion. The mechanistic elucidation is well supported by control experiment and literature precedents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hai-Qing Wang, Wenjing Ma, Ao Sun, Xin-Yue Sun, Chao Jiang, Yu-Chen Zhang, Feng Shi
Summary: A base-promoted cyclization method has been developed for generating aza-o-quinone methides from N-(o-chloromethyl)aryl amides, which react with azlactones to produce dihydroquinolinone derivatives in good yields (up to 98%). This approach not only advances reactions involving aza-o-quinone methides, but also provides a useful strategy for constructing biologically important dihydroquinolinone frameworks.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Dmitry Osipov, Maxim R. Demidov, Vitaly A. Osyanin, Yuri N. Klimochkin
Summary: A two-step procedure was proposed for the synthesis of 2-aryl- and 2,4-diaryl-substituted 4H-chromenes, involving a [4+1] cycloaddition reaction followed by reductive rearrangement under specific reagents.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2021)
Article
Chemistry, Multidisciplinary
Xue Song, Jie Zhang, Yu-Xing Wu, Qin Ouyang, Wei Du, Ying-Chun Chen
Summary: In this study, an asymmetric formal nucleophilic o-cresolylation reaction using palladium catalysis was reported. The reaction involved the generation of electron-neutral and HOMO-raised eta(2)-Pd(0)-dienone complexes, followed by vinylogous addition and a cascade of isomerization/elimination/aromatization processes. The use of a bulky chiral phosphonamidite ligand achieved moderate to excellent diastereo- and enantioselectivity, allowing facile access to diverse enantioenriched architectures. Control experiments provided detailed insights into the catalytic reaction pathway.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Xiaoqing Wang, Yuqing Bai, Xiaoyong Zhai, Bo Wu, Yonggui Zhou
Summary: An environmentally sustainable copper-catalyzed dehydrocoupling polymerization method was developed for efficient preparation of poly(silyl ether)s (PSEs) with high yields and molecular weight. The PSEs exhibit good thermal stability and low glass-transition temperature.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Shao-Jie Cheng, Gang Wang, Kui Liu, Zhi-Shi Ye
Summary: A palladium-catalyzed regioselective alpha-amino C-H functionalization has been established via the isomerization of alpha,beta-unsaturated carbonyls including esters, ketones, and amides, providing a straightforward access to a wide range of multicyclic compounds with good yields. This transformation exhibits high regioselectivity, excellent functional group tolerance, and scalability.
Article
Chemistry, Organic
Jie Lin, Zilong Huang, Juan Ma, Bao-Hua Xu, Yong-Gui Zhou, Zhengkun Yu
Summary: Efficient palladium-catalyzed reactions were utilized to synthesize diverse compounds, including trisubstituted 1,3-dienes and tetrasubstituted allenes. The chemo- and regioselectivities were controlled to obtain structurally diverse products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunlong Li, Wenchao Jiang, Jie Lin, Juan Ma, Bao-Hua Xu, Yong-Gui Zhou, Zhengkun Yu
Summary: In this study, triple C-H bond activation of aryl enaminones was achieved to access naphtho[1,8-bc]pyrans through oxidative annulation. Depending on the steric and/or electronic environment around the aryl moiety of the enaminones or the electronic impact from the alkynes, 1-naphthols might be formed as the sole products. By using propargyl alcohols as masked terminal alkynes, functionalized but-2-ene-1,4-diones were obtained through rhodium(III)- or rhodium(I)-catalyzed internal alkenyl C-H bond activation. The resulting naphtho[1,8-bc]pyrans exhibited high fluorescence and could be further transformed by chlorination, bromination, and difluoromethylation, demonstrating the potential applicability of the synthetic protocol.
Article
Chemistry, Applied
Zilong Huang, Jie Lin, Juan Ma, Liandi Wang, Yong-Gui Zhou, Zhengkun Yu
Summary: Carbene insertion into C(sp(2))-H bonds of internal alkenes was achieved in air using HFIP as both the mediator and solvent, along with borane B(C6F5)(3) as the catalyst. The reaction showed high yields (47-84%) and broad substituent tolerance, providing an efficient route to synthesize 3-vinylated oxindole and indole derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Xiang Li, Gao-Wei Wang, Li-Xia Liu, Chang-Bin Yu, Yong-Gui Zhou
Summary: Here, the authors describe the first example of palladium-catalyzed asymmetric hydrogenolysis of easily accessible aryl triflates for the construction of axially chiral biaryl scaffolds. The resulting chiral biaryl compounds were used to prepare axially chiral monophosphine ligands, which were further employed in palladium-catalyzed asymmetric allylic alkylation with excellent enantioselectivities and high branched and linear ratios, highlighting the potential utility of this methodology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tong Niu, Li-Xia Liu, Bo Wu, Yong-Gui Zhou
Summary: A series of [2,2]paracyclophane-based tridentate PNO ligands with planar chirality were designed and synthesized. These easily prepared chiral tridentate PNO ligands were successfully applied to the iridium-catalyzed asymmetric hydrogenation of simple ketones, providing chiral alcohols with high efficiency and excellent enantioselectivities (up to 99% yield and >99% ee). Control experiments demonstrated the indispensability of both N-H and O-H in the ligands.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zilong Huang, Jie Lin, Mingrui Li, Zhengkun Yu, Yong-Gui Zhou
Summary: A zinc(II)-catalyzed [2+2+1] annulation reaction of internal alkenes, diazooxindoles, and isocyanates was developed for the efficient synthesis of multisubstituted spirooxindoles. This multi-component transformation involves the in situ formation of a sulfur-containing spirocyclic intermediate, followed by a 1,3-dipolar addition reaction of the intermediate with the internal alkene, resulting in a formal [2+2+1] annulation in a one-pot manner. The synthetic protocol utilizes a low-toxicity main group metal catalyst, readily available reagents, and provides high yields of up to 96% for the synthesis of multisubstituted spirooxindole derivatives.
Review
Chemistry, Multidisciplinary
Xiao Xiao, Kaini Xu, Zhong-Hua Gao, Zhou-Hao Zhu, Changqing Ye, Baoguo Zhao, Sanzhong Luo, Song Ye, Yong-Gui Zhou, Senmiao Xu, Shou-Fei Zhu, Hongli Bao, Wei Sun, Xiaoming Wang, Kuiling Ding
Summary: Enzymes are essential for biological transformations and have attracted great attention for their structures and functions. Biomimetic chemistry has rapidly developed in response to the demand for bioactive molecules and efficient synthesis. Biomimetic asymmetric catalysis, inspired by enzymes, has been recognized as one of the most promising strategies for producing valuable chiral compounds. This review summarizes the evolution of biomimetic asymmetric catalysis in terms of biomimetic design, catalyst development, and catalytic transformations, providing insights into bridging the gap between bio-catalysis and chemical synthesis.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Zheng Liu, Sheng-Mei Lu, Bao-Qian Zhao, Hao-Dong Chen, Mu-Wang Chen, Yong-Gui Zhou
Summary: A method using zinc chloride was developed to purify compounds with pyridine structure from Mitsunobu reaction mixtures, and a sulfide anion was used to release bipyridines from Ullmann coupling reaction mixtures by competitively coordinating the copper ion. These improvements enabled the facile synthesis of the chiral 2,2'-bipyridine ligand (R-a,S,S)-C3-ACBP, achieving an overall yield of 48% at a 7 gram scale within 3-4 days without column chromatography.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Li-Xia Liu, Yu-Qing Bai, Xiang Li, Chang-Bin Yu, Yong-Gui Zhou
Summary: Combining base-promoted retro-sulfa-Michael addition with palladium-catalyzed asymmetric allenylic alkylation, a streamlined synthesis of chiral thiochromanones containing two central chiralities (including a quaternary stereogenic center) and an axial chirality (allene unit) was successfully achieved, with yields up to 98%, dr of 49.0:1, and >99% ee.
Article
Chemistry, Organic
Wen-Jun Huang, Li-Xia Liu, Yong-Gui Zhou, Bo Wu, Guo-Fang Jiang
Summary: We report a Bronsted acid-catalyzed C6 functionalization of 2,3-disubstituted indoles with 2,2-diarylacetonitriles for efficient construction of cyano-substituted all-carbon quaternary centers with excellent yields. The synthetic utility was demonstrated by the conversion of the cyano-group which enables the divergent preparation of aldehydes, primary amines and amides. Control experiments suggested that this process involves C-H oxidation of 2,2-diarylacetonitriles to in situ generate d,d-disubstituted p-quinone methide intermediates. This protocol provides an efficient method for C6 functionalization of 2,3-disubstituted indoles to construct all-carbon quaternary centers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yixuan Ding, Yonggui Zhou
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xi Yang, Gang Wang, Zhi-Shi Ye
Summary: In this study, a novel and efficient palladium-catalyzed reaction was disclosed for the simultaneous construction of heteroaromatic ring and methyl group, resulting in moderate to excellent yields. This methodology played a key role in the synthesis of pregnane X receptor antagonists.
Review
Chemistry, Multidisciplinary
Yuan He, Zilong Huang, Kaikai Wu, Juan Ma, Yong-Gui Zhou, Zhengkun Yu
Summary: C-H functionalization is an effective method for establishing carbon-carbon and carbon-heteroatom bonds, and has made significant progress. Transition-metal-catalyzed carbene insertion to C-H bonds is one of the hot research topics in this field, with various catalyst design strategies and synthetic methods. This review summarizes the research progress up to July 2021 and discusses future directions.
CHEMICAL SOCIETY REVIEWS
(2022)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
