Article
Chemistry, Organic
Hang Yan, Cui Zhang, Jiao-Jiao Han, Si-Si Du, Yuan-Zhao Hua, Min-Can Wang, Guang-Jian Mei, Shi-Kun Jia
Summary: We have developed a new strategy for the enantioselective cascade Michael/acyl transfer reaction of enynones and alpha-hydroxy aryl ketones catalyzed by dinuclear zinc cooperative catalysis. The reaction resulted in the synthesis of structurally diverse chiral 1,5-dicarbonyl compounds with good yields and excellent stereoselectivities. This strategy is notable for its broad substrate scope, high atom economy, and the utilization of enynones as efficient electrophilic acyl transfer reagents in asymmetric cascade reactions for the first time.
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
Li Jingjie, Wang Yuhao, Meng Tiantian, Huang Yiyong
Summary: A P(4-OMe-C6H4)(3)-catalyzed Michael addition/double bond migration tandem reaction between allenyl imide and indol-2-ones has been developed. This synthetic strategy allows for the synthesis of diverse 1,3-dihydro-3-alkylidene-2H-indol-2-ones and features operationally simple procedures, good substrate scope, high chemoselectivity, and mild reaction conditions. The proposed reaction mechanism is also elucidated.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Qifa Chen, Yue Teng, Fan Xu
Summary: In this study, a lanthanide silylamide-catalyzed tandem reaction was developed for the synthesis of pyrano[2,3-b]indol-2-ones in high yields. The catalytic activity of lanthanide amides may be influenced by the cooperation of the Lewis acidity of the lanthanide center and the Bronsted basicity of the N(SiMe3)(2) anion.
Article
Chemistry, Organic
Wen-Bi Hu, Yan-Qing Qiu, Wen-Yi Wei, Qing Li, Yan-Jun Xu
Summary: In this study, novel complex C2-quaternary-indol-3-one units bearing versatile nitro groups were successfully developed from pseudo-indolones and alpha,beta-unsaturated nitroolefins through rhodium-catalyzed C-H activation/[3 + 2] spirocyclization. Notably, four diastereomers could be selectively obtained in the reaction by condition control.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ling-Jun Li, Xing Wang, Hui Xu, Hui-Xiong Dai
Summary: Here, we present an efficient method for the synthesis of polysubstituted pentafulvenes through palladium-catalyzed deacetylative [2+2+1] annulation of enones with alkynes. Aryl-, alkenyl-, and alkyl-substituted alpha,beta-enones were used as suitable substrates, resulting in moderate to good yields of pentafulvene products. This method exhibits excellent compatibility with sensitive halides, free hydroxyl groups, and heterocycles. The one-pot gram-scale synthesis and further applications in the late-stage modification of natural products demonstrate the synthetic utility of this method.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chander Shekhar, Gedu Satyanarayana
Summary: In this study, a triflic acid-driven dual cyclization pathway was developed to produce functionalized molecules from readily available starting materials under metal-free conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jing Wang, Xiaoxue Zhang, Jianhui Zhou, Liping Yan, Yuan Li, Naixuan Zhao, Hong Liu, He Huang, Yu Zhou
Summary: A Ru(ii)-catalyzed C-H activation and annulation cascade was successfully developed for the construction of coumarin-fused benzo[a]quinolizin-4-ones and pyridin-2-ones. This reaction resulted in the formation of a unique 6-6-6-6-6 pentacyclic coumarin-fused scaffold through two successive C-H bond activations and [4 + 2] annulation cascade in a one-pot operation. The resulting products exhibited good affinity for the ENL YEATS domain.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Hao Xu, Yun-Xuan Tan, Pei-Pei Xie, Rui Ding, Qi Liao, Jian-Wei Zhang, Qing-Hua Li, Yu-Hui Wang, Xin Hong, Guo-Qiang Lin, Ping Tian
Summary: A rhodium(III)-catalyzed asymmetric reductive cyclization was reported for alpha,beta-unsaturated compounds tethered with cyclohexadienone, leading to cis-bicyclic frameworks with good yields and enantioselectivities. The role of ring strain in controlling regioselectivity and favoring 5,6-bicyclic products was also demonstrated by DFT calculations.
Article
Chemistry, Organic
Zhan-Yong Wang, Fumin Shen, Ting Yang, Jun-Kai Zhang, Rongxiang Chen, Kai-Kai Wang, Hongxin Liu
Summary: A novel method was developed for the construction of medicinally important spirobenzofuranone derivatives using an NHC mediated three-component cascade reaction with mild reaction conditions. The reaction generates three consecutive stereocenters, including an all-carbon substitution, and can accommodate various substituents and substitution patterns, affording the products in moderate to good yields with excellent diastereoselectivities and moderate enantioselectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hideo Setsumasa, Kosuke Imai, Ikumi Kobayashi, Masahisa Nakada
Summary: The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and 69% yield (1/11 cis/trans), respectively.
Article
Chemistry, Organic
Hideo Setsumasa, Kosuke Imai, Ikumi Kobayashi, Masahisa Nakada
Summary: This study describes the Pd-catalyzed stereoselective synthesis of decalins with one-carbon units bearing heteroatoms at the ring junction. The Pd-catalyzed cyclization of silyl enol ether resulted in the exclusive formation of the cis isomer (89%, >100/1 cis/trans). Conversely, Pd-catalyzed carboiodination and carboborylation reactions (with oxidative workup) provided products with yields of 56% (1/>100 cis/trans) and 69% (1/11 cis/trans), respectively.
Article
Chemistry, Multidisciplinary
Wen-Lei Xu, Wei-Ming Zhao, Ru-Xia Zhang, Jie Chen, Ling Zhou
Summary: The translation introduces a new and efficient method for synthesizing axially chiral aryl-C3-benzoindoles, explaining the success of the strategy in detail.
Article
Chemistry, Organic
Min Liu, Jiaxin Huang, Hui Xu, Hui-Xiong Dai
Summary: In this study, exo-chalcogenated methylene chroman-3-ones were synthesized via a palladium-catalyzed intramolecular acyl-chalcogenation of alkyne with thio- and selenoesters. The method exhibited high stereoselectivity and tolerated various functional groups and heterocycles, providing moderate-to-good yields of chroman-3-one products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Daniel J. Leonard, John W. Ward, Jonathan Clayden
Article
Chemistry, Organic
Mostafa Mahmoud Amer, Hossay Abas, Daniel J. Leonard, John W. Ward, Jonathan Clayden
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Kewei Wang, Zhifang Jia, Yang Bai, Xue Wang, Sophie E. Hodgkiss, Linjiang Chen, Samantha Y. Chong, Xiaoyan Wang, Haofan Yang, Yongjie Xu, Feng Feng, John W. Ward, Andrew Cooper
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Jonathan C. Golec, Eve M. Carter, John W. Ward, William G. Whittingham, Luis Simon, Robert S. Paton, Darren J. Dixon
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Xue Wang, Mounib Bahri, Zhiwei Fu, Marc A. Little, Lunjie Liu, Hongjun Niu, Nigel D. Browning, Samantha Y. Chong, Linjiang Chen, John W. Ward, Andrew Cooper
Summary: By using tetrahedral spiroborate linkages, square-planar cobalt(II) phthalocyanine units are assembled into a 3D COF with noninterpenetrated nbo topology, exhibiting high crystallinity and long-range order. The COF has cubic pores and permanent porosity, with a BET surface area of 1726 m(2) g(-1).
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Wei Zhao, Peiyao Yan, Boyu Li, Mounib Bahri, Lunjie Liu, Xiang Zhou, Rob Clowes, Nigel D. Browning, Yue Wu, John W. Ward, Andrew Cooper
Summary: A high-throughput sonochemical synthesis and testing strategy was developed to discover covalent organic frameworks (COFs) for photocatalysis. Among the screened COFs, one showed excellent photocatalytic activity for hydrogen peroxide production, but its activity decreased after long-term testing. The introduction of a two-phase catalytic system greatly enhanced its photostability.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Sriram Vijayakrishnan, John W. Ward, Andrew I. Cooper
Summary: In this study, a novel photocatalyst CTF-2 was discovered for decarboxylative conjugate addition under visible-light irradiation. CTF-2 showed the ability to couple with various other reactions and can be prepared on a large scale with recyclability.
Article
Chemistry, Multidisciplinary
Caitlin E. Shields, Xue Wang, Thomas Fellowes, Rob Clowes, Linjiang Chen, Graeme M. Day, Anna G. Slater, John W. Ward, Marc A. Little, Andrew I. Cooper
Summary: Designing hydrogen-bonded organic frameworks (HOFs) with low densities and high porosities is challenging due to the preference for close packing in most molecules. Crystal structure prediction (CSP) can rank alternative crystal packings for organic molecules based on their lattice energies. By combining CSP with structure-property predictions, a previously unknown low-energy HOF (TH5-A) with remarkably low density and three-dimensional pores was discovered for triptycene trisquinoxalinedione (TH5). This TH5-A polymorph demonstrates high porosity with a surface area of 3,284 m(2) g(-1), making it one of the most porous HOFs reported.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
David T. J. Morris, Steven M. Wales, Javier Echavarren, Matej Zabka, Giulia Marsico, John W. Ward, Natalie E. Pridmore, Jonathan Clayden
Summary: Cyclic triureas derived from TACN were synthesized and characterized. Dynamic cyclochirality was observed, with the hydrogen-bonded urea groups exchanging enantiomers through bowl inversion and directionality reversal. Structural modifications were found to affect the enantiomerization barrier, resulting in a planar-chiral, atropisomeric bowl-shaped structure with high stereochemical stability solely from its hydrogen-bonding network.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Sriram Vijayakrishnan, John W. Ward, Andrew I. Cooper
Summary: Photoredox catalysis is an important development in organic synthesis, but the current use of homogeneous metal complexes or organic dyes raises issues of cost, recyclability, and waste production. In this study, a covalent triazine framework photocatalyst (CTF-2) was discovered, which enables decarboxylative conjugate addition of carboxylic acids under visible-light irradiation. CTF-2 can be prepared on a large scale and recycled without loss of catalytic efficiency.
Article
Chemistry, Multidisciplinary
Louise Eagling, Daniel J. Leonard, Maria Schwarz, Inaki Urruzuno, Grace Boden, J. Steven Wailes, John W. Ward, Jonathan Clayden
Summary: l-Arogenate is a key metabolite in the synthesis of plant secondary metabolites, with a practical synthesis method involving carboxylative dearomatization by intramolecular electrophilic capture to generate a versatile intermediate for further functionalization.
Article
Chemistry, Multidisciplinary
Daniel J. Leonard, Francis Zieleniewski, Isabelle Wellhofer, Emily G. Baker, John W. Ward, Derek N. Woolfson, Jonathan Clayden
Summary: The study demonstrates the successful incorporation of Q4As into peptides, allowing for the synthesis of monomeric and dimeric alpha-helical peptides with varying degrees of Q4A substitution. Both enantiomers of Q4As are tolerated in folded monomeric and oligomeric alpha-helical peptides, with the (R)-enantiomer being slightly more favorable than the (S).
Article
Chemistry, Multidisciplinary
Makenzie J. Millward, Emily Ellis, John W. Ward, Jonathan Clayden
Summary: In this study, bicyclic or tricyclic nitrogen-containing heterocyclic scaffolds were rapidly constructed by intramolecular nucleophilic aromatic substitution of metallated nitriles tethered to a series of electronically unactivated heterocyclic precursors. The substitution reaction enables a ring expansion, facilitated by the conformationally constrained tether between the nitrile and the heterocycle. X-ray crystallography revealed ring-dependant strain within the hydantoin intermediate.
Article
Chemistry, Physical
Yongjie Xu, Reiner Sebastian Sprick, Nick J. Brownbill, Frederic Blanc, Qingyin Li, John W. Ward, Shijie Ren, Andrew Cooper
Summary: In this study, a new 2D porous carbon material 2D-PCM was successfully synthesized using a wet-chemical synthesis method, showing excellent electrochemical performance that surpasses state-of-the-art carbon materials. Comparison with top-down processing routes suggests that wet-chemical methods may have certain advantages in the synthesis of 2D materials.
JOURNAL OF MATERIALS CHEMISTRY A
(2021)
Article
Chemistry, Multidisciplinary
Rakesh K. Saunthwal, Matthew T. Cornall, Roman Abrams, John W. Ward, Jonathan Clayden
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)
