Article
Chemistry, Multidisciplinary
Sushant Aryal, Christopher A. Hone, Matthew I. J. Polson, Daniel J. Foley
Summary: We report a single-step enantioselective synthesis of 5-monosubstituted hydantoins via condensation of glyoxals and ureas in the presence of a chiral phosphoric acid at room temperature. The products were obtained in up to 99% yield and 98:2 enantiomeric ratio. Mechanistic and kinetic studies revealed that the reaction likely proceeds via face-selective protonation of an enol-type intermediate.
Article
Chemistry, Organic
Shuang-Shuang Ma, Rui Sun, Zi-Heng Zhang, Zheng-Kun Yu, Bao-Hua Xu
Summary: The alkylation of nitroarenes with alkanols catalyzed by a phosphinesulfonate chelated ruthenium complex [Ru-1] exhibits diverse reactivity and chemoselectivity depending on the acidic-basic conditions. This catalyst can promote the formation of secondary and tertiary anilines under neutral or acidic conditions, while enabling N-monoalkylation of nitroarenes with primary alkanols under alkaline conditions through a concerted approach. Mechanistic studies showed that the O-H activation of alkanols assisted by the sulfonate ligand is crucial in the novel reactivity observed under alkaline-free conditions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Yuan Cai, Lin-Xin Ruan, Abdul Rahman, Shi-Liang Shi
Summary: This study reports a highly efficient NHC/Ni-catalyzed addition reaction of arylboronic esters to ketones, providing rapid access to chiral tertiary alcohols with broad substrate scope and excellent functional group tolerance. The reaction differs from other Ni-mediated reactions, exhibiting good specificity and tolerance to various functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Rong Zhao, Jiangge Teng, Zhiwei Wang, Wenwen Dong, Jia Lin, Changhu Chu
Summary: A highly efficient oxidation method of alpha-diazo esters to alpha-ketoesters using a Cu/C catalyst has been developed, with the mechanism proceeding through a radical pathway. The reaction can be inhibited by the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, and a disproportionation reaction can occur between alpha-diazo ester and water.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shinnosuke Kitayama, Hiroaki Shimizu, Satoshi Yokoshima
Summary: In this study, photoirradiation of alpha-(2-nitrophenyl)ketones resulted in the production of cyclic hydroxamates. The reaction involved photoinduced oxygen transfer from the nitro group to the benzylic position, leading to the formation of an alpha-hydroxyketone with a nitroso group. Subsequent addition of the nitroso group to the ketone moiety and the cleavage of the C-C sigma bond between the carbonyl group and the benzyl position produced hydroxamic acid, which then underwent hemiacetal formation to yield cyclic hydroxamate.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yasushi Yoshida, Reina Kasuya, Takashi Mino, Masami Sakamoto
Summary: The first phase-transfer catalyzed asymmetric synthesis of alpha-chiral tetrasubstituted alpha-aminothioesters has been reported in this study, affording products with up to 81% ee. This work fills a gap in the limited existing literature on the asymmetric synthesis of these important scaffolds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Meng Li, Guang-Rui Peng, Xuan Yang, Zhen-Ning Ma, Jian-Bo Xie
Summary: We developed a copper-catalyzed enantio- and diastereoselective boron conjugate addition method for α-alkyl α,beta-unsaturated esters under base-free conditions. The approach exhibited excellent enantioselectivities and moderate to good conversions, although with moderate diastereoselectivities. The synthetic utility of this protocol was demonstrated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Yao Zhang, Deyong Qiao, Mei Duan, You Wang, Shaolin Zhu
Summary: In this study, a new synthetic method was reported for the highly enantioselective synthesis of chiral alpha-aminoboronates and their derivatives under mild conditions. The method was demonstrated to be efficient for the synthesis of a current pharmaceutical agent.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Christopher Mairhofer, Victoria Haider, Thomas Bogl, Mario Waser
Summary: The deoxyfluorination of cyclic alpha-hydroxy-beta-ketoesters using DAST reported in this study demonstrates high levels of stereospecificity, resulting in the configurationally inverted alpha-fluoro-beta-ketoesters in high yields under simple operation conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Ruisheng Liu, Qishun Liu, Haoran Meng, Hongyu Ding, Jindong Hao, Zhongyin Ji, Huilan Yue, Wei Wei
Summary: A metal-free, visible-light-promoted strategy has been developed for the construction of alpha-ketoesters via aerobic oxidation of alpha-diazoesters with dioxygen at room temperature. Using cheap Eosin Y as the photocatalyst and O-2(air) as the oxidant, this protocol offers a mild and efficient approach to a wide range of alpha-ketoesters in moderate to good yields. Preliminary mechanistic studies indicate the involvement of photo-excited singlet oxygen in the reaction system.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Yingang Wang, Jinhui Feng, Wenyue Dong, Xi Chen, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Summary: The study successfully engineered an omega-transaminase with (S)-selectivity to accept bulky substrates, resulting in several variants that showed activity towards bulky substrates, with the best variant achieving high yield and enantioselectivity in the asymmetric synthesis at a semi-preparative scale. This work will enhance the general understanding of omega-transaminases and inspire further engineering efforts to reverse enantio-specificity.
Article
Chemistry, Organic
Hualing He, Xiaoxue Tang, Yang Cao, Jon C. Antilla
Summary: A catalytic enantioselective reduction of alpha-trifluoromethylated imines has been developed using a BINOL-derived boro-phosphate as catalyst and catecholborane as hydride source. This method provides an efficient route to prepare synthetically useful chiral alpha-trifluoromethylated amines in high yields and excellent enantioselectivities under mild conditions (up to 98% yield and 96% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Vasileios Giannopoulos, Ioulia Smonou
Summary: An enzymatic approach for the asymmetric reduction of alpha,alpha-dichloro-beta-keto esters has been developed, leading to the synthesis of enantiomerically pure (S)-alpha,alpha-dichloro-beta-hydroxy esters in a single step.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wengang Guo, Min Wang, Zhengyu Han, Hai Huang, Jianwei Sun
Summary: The research describes the first organocatalytic asymmetric N-H insertion reaction using alpha-carbonyl sulfoxonium ylides, providing efficient access to alpha-aryl glycines with excellent enantiocontrol. The high stability and weak basicity of sulfoxonium ylides make this protocol user-friendly and practically useful, with detailed mechanistic studies revealing reversible protonation and rate-determining C-N bond formation.
Article
Chemistry, Physical
Durgaiah Chevella, Chiranjeevi Thota, Supriyo Majumder
Summary: The synthesis of esters and keto esters via retro-Claisen condensation of alcohols with ss-diketones in the presence of a commercially available heterogeneous catalyst, Amberlyst-15, was reported. Several industrially relevant acetates were synthesized in multi-gram scale, and long chain keto-esters were obtained in excellent yields. The protocol allows for a practical approach for large scale ester synthesis and the catalyst can be reused for multiple cycles.
MOLECULAR CATALYSIS
(2023)
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)