Article
Biochemistry & Molecular Biology
Andrew McGown, Anthony K. Edmonds, Daniel Guest, Verity L. Holmes, Chris Dadswell, Ramon Gonzalez-Mendez, Charles A. Goodall, Mark C. Bagley, Barnaby W. Greenland, John Spencer
Summary: The study demonstrates that a cheap and conventional sealed heating reactor can be a valuable alternative to a microwave reactor for synthesizing a large-scale MIDA boronate library, with shorter reaction times and energy and solvent savings.
Article
Chemistry, Multidisciplinary
Yangyang Yang, Jet Tsien, Ryan Dykstra, Si-Jie Chen, James B. Wang, Rohan R. Merchant, Jonathan M. E. Hughes, Byron K. Peters, Osvaldo Gutierrez, Tian Qin
Summary: A programmable bisfunctionalization strategy is reported in this study to enable late-stage sequential derivatization of BCP bis-boronates, opening up opportunities to explore the SARs of drug candidates possessing multisubstituted BCP motifs.
Article
Chemistry, Multidisciplinary
Claudius D'Silva
Summary: The researchers investigated three different routes for synthesizing 1-(4-boronobenzyl)-1H-pyrrole, and found that the route involving the introduction of the boronate group as the final step of the reaction turned out to be successful.
JOURNAL OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Qiqiang Xie, Guangbin Dong
Summary: The Matteson-type reactions have gained increasing interest in organic synthesis, but current tactics mainly focus on carbon chains. In this study, we report the development of the oxa-Matteson reaction, which allows oxygen and carbenoid insertions into alkyl- and arylboronates, leading to the synthesis of boron-substituted ethers. The method demonstrates its utility in the preparation of functional ethers, asymmetric synthesis, and programmable construction of polyethers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Sufal Paul, Piyush Kumar Verma, Anubhab Kashyap, Rahul Mondal, K. Geetharani
Summary: A new method has been developed for sequentially gem-thioborylating readily available aldehydes through cobalt-catalyzed diboration reaction. The N-heterocyclic carbene (NHC)-cobalt complex serves as a catalyst for the diboration of aldehydes to generate alpha-oxyl boronic esters, which react with lithium thiolates to form a tetracoordinate boronate species undergoing 1,2-metalate rearrangement in the presence of trifluoroacetic anhydride. The stepwise functionalization of the boryl and thiol moiety of the products enriches the chemical toolbox of diverse organic synthesis.
Article
Chemistry, Organic
R. Rengasamy, K. Vijayalakshmi, N. Punitha, J. Paul Raj, K. Karthikeyan, J. Elangovan
Summary: A collection of 1,4-disubstituted 1,2,3-triazoles was synthesized via decarboxylative [3 + 2] cycloaddition of organic azides and cinnamic acids. The protocol features metal-free conditions, high regioselectivity, and easy accessibility of starting materials.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Alexander N. Koronatov, Kseniia K. Afanaseva, Pavel A. Sakharov, Nikolai V. Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A new method for the synthesis of 1-alkyl-3-sulfonamido-1H-pyrroles via the Rh(ii)-catalyzed denitrogenative coupling of two different types of 1,2,3-triazoles has been developed. The reaction mechanism involves the attack of the rhodium-bound azavinyl carbene, leading to the formation of metal-free ylides and subsequent conversion to the desired products. This protocol provides high yields of 3-sulfonamidopyrroles, demonstrating promising synthetic applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Multidisciplinary Sciences
Purui Zheng, Pan Zhou, Dong Wang, Wenhao Xu, Hepan Wang, Tao Xu
Summary: The authors reported a mild Ni/photoredox-catalyzed reductive cross-coupling of aryl iodides and alpha -chloroboranes, enriching the metallaphotoredox chemistry. This method enables the access to versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities under mild conditions.
NATURE COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Mary C. C. Hennessy, Hirenkumar Gandhi, Timothy P. P. O'Sullivan
Summary: A methodology for synthesizing γ, δ-unsaturated β-keto esters through asymmetric peroxidation is described. The cinchona-derived organocatalyst allows for high enantioselectivity (up to 95:5) in obtaining the desired γ-peroxy-β-keto esters. Furthermore, the resulting δ-peroxy esters can be easily reduced to chiral δ-hydroxy-β-keto esters without affecting the functionality of the β-keto ester. Importantly, this chemistry provides a concise route to chiral 1,2-dioxolanes, a common motif in bioactive natural products, via a novel P2O5-mediated cyclization of the corresponding δ-peroxy-β-hydroxy esters.
Article
Chemistry, Multidisciplinary
Tianhang Wang, Minyan Wang, Yandong Wang, Mingjie Li, Yuan Zheng, Qianwei Chen, Yue Zhao, Zhuangzhi Shi
Summary: This study reports a catalytic enantioselective hydroboration through desymmetrization of enantiotopic carbons in cyclopropanes. Treatment of cyclopropanes bearing an amide directing group with rhodium catalysis using HBpin as a boron source allows the construction of alkyl boronates containing γ-stereogenic amines. Ligand cooperativity of an exogenous chiral phosphite and an endogenous acetylacetonate plays a key role in achieving high enantioselectivity. Detailed experimental and computational studies elucidate the effect of ligand cooperativity and the key steps involved in the reaction.
Article
Chemistry, Organic
Xiaoping Fu, Qingqing Qi, Shiqing Xu, Ei-ichi Negishi
Summary: A new imine-induced 1,2-boronate migration has been developed for achieving chemo- and stereoselective dearomative coupling of C3-substituted indoles and bi-electrophilic beta-imino boronic esters, providing rapid access to complex chiral indoline boronic esters with four stereocenters. Conversely, coupling of indoles without C3 substitution and beta-imino boronic esters leads to tetrahydro-1H-pyrido[4,3-b]indoles through imine-induced 1,2-boronate migration followed by deborylative rearomatization.
Article
Chemistry, Organic
Tongchang Fang, Jian Qiu, Kai Yang, Qiuling Song
Summary: Organoboron compounds have diverse transformations of C-B bonds, and their synthetic application value can be greatly increased by introducing easy-to-transform functional groups. The first synthesis of sp(2)-alpha-haloboronates via an in situ alpha-sp(3)-boron radical intermediate proves their high synthetic application value.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Polymer Science
Xuexuan Fan, Linlin Wang, Shengyu Feng, Lei Li
Summary: Developing reprocessable polymeric materials from renewable biomass and earth-abundant elements is of great significance. By using biomass-derived gluconolactone, the synthesis process is simple and efficient, producing water as the only byproduct. The obtained materials have controllable mechanical properties, excellent thermal stability, and efficient healing capacity. They can be fabricated into transparent and luminescent coatings, showing potential applications in flexible optical devices.
MACROMOLECULAR RAPID COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Prabhat Ranjan, Serena Pillitteri, Guglielmo Coppola, Monica Oliva, Erik V. Van der Eycken, Upendra K. Sharma
Summary: This study demonstrates the use of amide solvents to modulate the oxidation potential of boronic acids for alkyl radical generation in visible-light-assisted photocatalyzed reactions. The developed protocol is simple and applicable for various reactions, including the synthesis of unnatural amino acids. Furthermore, selective generation of radical species from boronic acids in the presence of boronic ester-containing molecules is now feasible, allowing for potential boron-selective modifications.
Article
Chemistry, Multidisciplinary
Suguru Yoshida, Yuki Sakata, Yoshihiro Misawa, Takamoto Morita, Tomoko Kuribara, Harumi Ito, Yuka Koike, Isao Kii, Takamitsu Hosoya
Summary: Efficient consecutive formation of 1,2,3-triazoles using multiazide platforms has been achieved in this study. A four-step synthesis of tetrakis(triazoles) was successfully performed from a tetraazide platform molecule, based on the unique clickability of the 1-adamantyl azido group. This method was applied to the convergent synthesis of tetrafunctionalized probes in a modular synthetic manner.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Guangchen Li, Guangshuai Zhou, Daisy Zhang-Negrerie, Yunfei Du, Jianhui Huang, Kang Zhao
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Organic
Ranran Zhu, Yuntao Wang, Jialin Liu, Qing Wang, Jianhui Huang
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Organic
Yue Wang, Caifeng Li, Jianhui Huang
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Xiaoyu Xiong, Ranran Zhu, Lin Huang, Shuqin Chang, Jianhui Huang
Article
Chemistry, Organic
Ranran Zhu, Zheyuan Liu, Jie Chen, Xiaoyu Xiong, Yuntao Wang, Lin Huang, Jinshan Bai, Yanfeng Dang, Jianhui Huang
Review
Chemistry, Organic
Caifeng Li, Liu Liu, Xuegang Fu, Jianhui Huang
SYNTHESIS-STUTTGART
(2018)
Article
Chemistry, Organic
Ranran Zhu, Shaonan Lu, Qing Wang, Jinshan Bai, Yuntao Wang, Qingzhen Yu, Jianhui Huang
Article
Chemistry, Multidisciplinary
Xiaoxia Zhao, Jinshan Bai, Fanyun Zeng, Yufeng Xing, Ranran Zhu, Jianhui Huang
Article
Chemistry, Organic
E. Siyu, Jialin Liu, Yuting Yan, Xuegang Fu, Xueyan Huang, Fanyun Zeng, Fatal Malik, Jianhui Huang
CURRENT ORGANIC CHEMISTRY
(2020)
Review
Chemistry, Organic
Mengyu Qiu, Xuegang Fu, Peng Fu, Jianhui Huang
Summary: N-Heterocycles are important components in organic synthesis, medicinal chemistry, and materials science, but their construction using traditional methods often involves the preparation of reactive intermediates. Recent advances in the synthesis of N-heterocyclic compounds have provided efficient methods under different reaction modes, opening up new possibilities for future molecular design, synthesis, and applications.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xuegang Fu, Yuting Yan, Hexin Sun, Siying Li, Jianhui Huang
Summary: In this study, a naturally occurring alkaloid called aloperine was used as a chiral skeleton for the development of new ligands/catalysts in asymmetric synthesis. The Pd-catalyzed asymmetric hydroarylation using these chiral 1,3-diamine ligands showed high yields and enantioselectivities, indicating their potential in organocatalysis. This discovery opens up new possibilities in the design and development of natural product-inspired chiral ligands.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xuegang Fu, Yue Wang, Liu Liu, Caifeng Li, Lin Huang, Jianhui Huang
Summary: A convenient dehydrogenation process using readily available inorganic base ((KOBu)-Bu-t) and oxygen has been reported. The process follows an S(RN)1 pathway and is followed by a radical elimination reaction. This radical process opens up possibilities for the development of new synthetic methodologies using (KOBu)-Bu-t as a single electron reductant.
Article
Chemistry, Organic
Nan Ma, Zheyuan Liu, Jianhui Huang, Yanfeng Dang
Summary: Density functional theory calculations have revealed the mechanism and origins of the reactivity and regioselectivity of the Cp*Ir(iii)/Cp*Rh(iii)-catalyzed allylic C-H amidation. The rate-determining step is found to be the C-H activation, which differs between the Cp*Ir(iii) and Cp*Rh(iii) systems, affecting their reactivity and regioselectivity. The insights provided by this study will be valuable for the development of transition metal-catalyzed selective C-H amination reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuntao Wang, Jialin Liu, Lin Huang, Ranran Zhu, Xueyan Huang, Ross Moir, Jianhui Huang
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Zenghua Chen, Le'an Hu, Fanyun Zeng, Ranran Zhu, Shasha Zheng, Qingzhen Yu, Jianhui Huang
CHEMICAL COMMUNICATIONS
(2017)
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)
