Article
Chemistry, Organic
Xiaojing Xu, Huan Luo, Jiayi Shen, Jing Chen, Jie Ye, Ze-Feng Xu, Chuan-Ying Li
Summary: Valuable piperidin-4-one derivatives were synthesized efficiently via an α-imino carbene-initiated cascade reaction, demonstrating excellent alkyl migration selectivity facilitated by 2-bromoethyl neighboring group participation. This protocol is characterized by high efficiency, excellent migrating selectivity, broad substrate scope, and convenient one-pot procedure, making it an effective tool for piperidine derivative synthesis. The migration-annulation reaction of α-imino carbene presents a powerful strategy for heterocycle construction.
Article
Chemistry, Multidisciplinary
Peiran Ruan, Cefei Zhang, Jin Wu, Fengnan Xiao, Yongyan Zhang, Qingfa Tan, Zhishan Su, Xiaoming Feng, Xiaohua Liu
Summary: By utilizing newly designed alpha-imino amide surrogates and azlactones as reactants, catalyzed by a chiral bifunctional guanidine, the construction of chiral 3,4-diaminopyrrolidine-2,5-diones and their derivatives was achieved through formal [3+2]-cyclization. The DFT calculations confirmed the role of guanidine as a multiple hydrogen bond donor.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Zhenghui Kang, Wenju Chang, Xue Tian, Xiang Fu, Wenxuan Zhao, Xinfang Xu, Yong Liang, Wenhao Hu
Summary: The study presents a novel asymmetric allylation reaction through ternary cooperative catalysis, enabling the expedient access to chiral alpha,alpha-disubstituted ketones with high enantioselectivity. Experimental and computational studies have elucidated the mechanism and origin of enantioselectivity in this three-component reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Kaixuan Wang, Longqing Yang, Yi Li, Hongye Li, Zhili Liu, Lichao Ning, Xiaohua Liu, Xiaoming Feng
Summary: We have developed a highly efficient formal [1,2]-sigmatropic rearrangement for the generation of ammonium ylides from 3-methylene-azetidines and a-diazo pyrazoamides. By employing a readily available chiral cobalt(II) complex of chiral N,N'-dioxide, we achieved ring expansion of azetidines to afford various quaternary prolineamide derivatives with excellent yield (up to 99%) and enantioselectivity (up to 99% ee) under mild reaction conditions. The installation of a pyrazoamide group as a masked brick to build chiral scaffolds proved successful for the rearrangement of ammonium ylides, and the enantioselective ring expansion process was elucidated by DFT calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Zhou-Hao Zhu, Yi-Xuan Ding, Bo Wu, Yong-Gui Zhou
Summary: The asymmetric reduction of tetrasubstituted olefins has seen significant development, leading to an urgent demand for an effective method. By mimicking the coenzyme NAD(P)H, researchers have successfully reduced 2,3-substituted 1H-inden-1-ones using the catalytic chiral NAD(P)H model CYNAM, achieving high yields (up to 98%) and good enantioselectivity (up to 99% ee). The reduced product can also be efficiently used for the concise synthesis of chiral bioactive molecules.
Article
Chemistry, Organic
Su Zhou, Qianqian Liu, Ming Bao, Jie Huang, Junjian Wang, Wenhao Hu, Xinfang Xu
Summary: A new synthesis method for 2-indolyl indolone N-oxides via gold(i)-catalyzed cascade reaction of o-nitroalkynes with indoles has been developed, leading to highly efficient conversion into 2-indolylbenzoxazinone with strong blue fluorescence. The synthesized compounds were also evaluated for their antitumor activity in small cell lung cancer, with compounds 3d and 4s showing high anticancer potency against SCLC cells.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Lu Han, Xue-Ting Zhang, Dong Xie, Shi-Kai Tian
Summary: An unprecedented [2,3]-sigmatropic rearrangement reaction has been established using quaternary 2,3-allenylammonium ylides generated in situ from tertiary 2,3-allenylamines and arynes. The reaction, which proceeds smoothly at room temperature, delivers structurally diverse products in moderate to excellent yields and is tolerant to a wide variety of functional groups. This reaction is carried out without the need for strong bases or transition metals, making it a versatile and convenient method for organic synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Rong Zeng, Zheng Wang, Ruikun Peng, Peng Yan, Jie Yang, Qian Zhou, Jing Gu, Peng-Fei Zheng, Ying-Chun Chen, Qin Ouyang
Summary: Through density functional theory (DFT) calculations, the mechanism of the (4 + 1 + 1) annulations between alpha-bromo carbonyls and 1-azadienes was investigated, and the formation of a carbon anion intermediate and its attack on another alpha-bromo carbonyl substrate in a (4 + 1 + 1) manner were proposed as more reasonable processes. Based on this, a new controllable divergent (4 + 1 + 1 ') reaction was achieved by changing the feeding sequence of two different alpha-bromo substrates in the presence of tertiary amines and bases, resulting in the efficient construction of a series of fused benzofuro[3,2-b]pyridines or benzo[4,5]thieno[3,2-b]pyridines with more functional diversity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Xin Chang, Xiang Cheng, Chun-Jiang Wang
Summary: This article introduces an efficient method for synthesizing pharmaceutical compounds with deuterium labels, which addresses the challenge of building deuterium-containing stereogenic centers in organic synthesis. By combining H/D exchange and 1,3-dipolar cycloaddition in a catalytic asymmetric strategy, bioactive alpha-deuterated pyrrolidine derivatives were constructed with high yields and excellent stereoselectivities.
Article
Chemistry, Organic
Yuya Araki, Masato Hanada, Yoshiko Iguchi, Haruki Mizoguchi, Akira Sakakura
Summary: This report describes the enantioselective direct-aldol reaction of alpha-imino esters with glyoxylate esters using a catalytic amount of Co(OAc)(2)-pybox complex. The reaction achieved good yield and enantioselectivity. The N-Boc-protected amino acid derivatives were obtained through hydrolysis of the imine moiety and Boc protection of the aldol products.
Article
Chemistry, Physical
Alexandra Jorea, Carlotta Raviola, Mariateresa Giustiniano, Davide Ravelli
Summary: A library of unnatural a-amino acid derivatives was synthesized by hydrofunctionalization of the C=N bond in a series of compounds. Tetrabutylammonium decatungstate was used as the photocatalyst to generate C-centered radicals, leading to the formation of (protected) a-hydrazino acids as products. This methodology proved to be versatile, allowing functionalization of the herbicide safener isoxadifen-ethyl.
Review
Chemistry, Organic
Pavel Yu Ushakov, Sema L. Loffe, Alexey Yu Sukhorukov
Summary: This review summarizes the advancements made in [4 + 1]-annulation reactions involving sulfonium, sulfoxonium, and ammonium ylides, as well as diazo compounds and carbenes over the past six years. The newly emerged methods for generating A(4)-synthons, such as radical, transition metal-catalyzed, and photo-redox processes, are outlined. Specific focus is given to the progress in asymmetric [4 + 1]-annulations using organocatalysis and chiral ammonium ylides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Song Xi, Yan Jiang, Jiaojiao Yang, Jiao Yang, Dingyin Miao, Baoyi Chen, Wanqiu Huang, Ling He, Hanyue Qiu, Min Zhang
Summary: A sequence of reactions has been developed to synthesize bicyclic indolizidines with bridgehead aza-quaternary stereocenters from chiral cyclopropyl ketones. The reactions proceed with excellent chirality transfer, tolerating various functional groups and producing products with high enantiomeric purities.
Article
Chemistry, Multidisciplinary
Jiawen Lang, Siyuan Wang, Changli He, Xiaohua Liu, Xiaoming Feng
Summary: An efficient asymmetric synthesis of isochromanone derivatives was achieved through Z-selective 1,3-OH insertion/aldol cyclization reaction using acyclic carboxylic oxonium ylides. The use of specific chiral catalysts and substrates enabled the cascade reaction with good stereochemistry control. This strategy provides a practical approach to access benzo-fused delta-lactones with vicinal quaternary stereocenters.
Article
Chemistry, Organic
Min Li, Yihua Chen, Yingkun Yan, Min Liu, Min Huang, Wenzhe Li, Lianyi Cao, Xiaomei Zhang
Summary: An enantioselective addition reaction catalyzed by a chiral phosphoric acid has been developed for the synthesis of quaternary alpha-isoxazole-alpha-alkynyl amino acid derivatives. The reaction showed high yields and good to excellent enantioselectivities, and the hydrogen-bonding interaction between the amino-isoxazole and chiral phosphoric acid played a vital role in the selectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dan Ni, Longlong Song, Yun Zhao, Shunying Liu
Summary: A Rh(II)/boron reagent co-catalyzed transformation was developed for the efficient synthesis of multi-substituted conjugated dienones under mild conditions. By trapping allene carbocations with oxonium ylides, two C=C double bonds, one C-C single bond, and one C-O single bond were constructed in yields up to 85%. Furthermore, a diversity-oriented strategy was established for the synthesis of alkyne ether and dihydrofuran derivatives in a substrate-dependent manner.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xiangrong Liu, Xue Tian, Jiawu Huang, Yu Qian, Xinfang Xu, Zhenghui Kang, Wenhao Hu
Summary: An enantioselective three-component reaction of alpha-propargylic-3-indolymethanol with diazoindolinone and alcohol has been achieved under the cocatalysis of Rh(II) and chiral phosphoric acid (CPA). The reaction proceeds through regio- and enantiospecific addition of an in situ formed oxonium ylide to the alpha-propargylic indole iminium ion, providing an efficient access to chiral propargylic indole derivatives with high yields and enantioselectivities.
Article
Oncology
Weining Weng, Tao Meng, Qianqian Zhao, Yi Shen, Guoxiang Fu, Jing Shi, Yue Zhang, Zhaohui Wang, Mingqiao Wang, Rong Pan, Linjie Ma, Caiwei Chen, Lijun Wang, Biao Zhou, Hui Zhang, Junyi Pu, Jianjian Zhang, Yi Peter Hu, Guoqiang Hua, Yu Qian, Shu-Hui Liu, Wenhao Hu, Xun Meng
Summary: This study introduces a novel class of ADCs with a self-immolative T moiety for traceless conjugation and release of exatecan. These ADCs overcome resistance faced by equivalent DXd/SN-38 ADCs in low-target-expression, large, and MDR+ tumors, and show synergy with PARP/ATR inhibitor and anti-PD-1 treatment.
Article
Oncology
Weining Weng, Tao Meng, Junyi Pu, Linjie Ma, Yi Shen, Zhaohui Wang, Rong Pan, Mingqiao Wang, Caiwei Chen, Lijun Wang, Jianjian Zhang, Biao Zhou, Siyuan Shao, Yu Qian, Shuhui Liu, Wenhao Hu, Xun Meng
Summary: HER3 is a tyrosine kinase belonging to the EGFR family and is widely expressed in various cancers. U3-1402/Patritumab-GGFG-DXd is the first successful HER3-targeting antibody-drug conjugate (ADC) with clinical efficacy in non-small cell lung cancer. However, nonresponsiveness and low target expression levels limit its effectiveness. AMT-562, a novel ADC that combines a modified anti-HER3 antibody and exatecan, showed potent and durable antitumor response in various cancer models, including colorectal cancer, and demonstrated higher synergistic efficacy in combination therapies compared to U3-1402. The pharmacokinetic and safety profiles of AMT-562 were favorable, making it a promising option for HER3-targeted therapy.
MOLECULAR CANCER THERAPEUTICS
(2023)
Article
Oncology
Chao Kong, Junyi Pu, Qianqian Zhao, Weining Weng, Linjie Ma, Yu Qian, Wenhao Hu, Xun Meng, Tao Meng
Summary: In this study, a novel PTK7-targeting antibody-drug conjugate (ADC) MTX-13 was designed, which exhibited potent anti-tumor activity and bystander killing through DNA damage and apoptosis induction, showing superior efficacy to current PTK7-targeting ADCs in a wide range of solid tumors.
MOLECULAR CANCER THERAPEUTICS
(2023)
Article
Chemistry, Physical
Longlong Song, Lulu Xiong, Dan Ni, Weixiong Chen, Jian Ji, Jian Xue, Xuwen Chen, Xiang Wu, Xiao He, Shunying Liu
Summary: Here, we report a [Pd-(eta(3)-C3H5)-Cl](2)/Sc-(OTf)(3)-catalyzed catalytic process accelerated by Bronsted acids with a beta-selective aza-Michael addition to yield a gamma-quaternary carbon. The triple co-catalytic system provides a strategy for the activation of vinyl-quinolines with a linear selectivity containing gamma-quaternary carbon, and the developed method shows a broad substrate scope, providing a general and rapid strategy for the quinoline-based diverse library construction.
Article
Chemistry, Organic
Cong Guan, Jiabin Yin, Jian Ji, Jinhua Liu, Xiang Wu, Tong Zhu, Shunying Liu
Summary: A regioselective electrochemical C-H amination method using easily accessible ethers has been developed to synthesize N (2)-substituted 1,2,3-triazole. Multiple substituents, including heterocycles, were well-tolerated, and 24 examples were obtained in moderate to good yields. Control experiments and DFT calculations revealed that the electrochemical synthesis occurs through a N-tosyl 1,2,3-triazole radical cation process, promoted by single-electron transfer from the lone pair electrons of the aromatic N-heterocycle, and the desulfonation is responsible for the high N (2)-regioselectivity.
Article
Chemistry, Organic
Rimei Zheng, Aimin Xu, Tianyuan Zhang, Pei Li, Maoqing Shi, Shanliang Dong, Wenhao Hu, Yu Qian
Summary: A novel and highly stereoselective acyclic 1,3-difunctionalization of vinyl metal carbene species has been developed via Rh(II)/chiral phosphoric acid co-catalyzed three-component reactions of vinyldiazoacetates with alcohols and imines. The reaction demonstrates excellent regio-, diastereo-, and enantioselectivities, and shows a broad scope and functional group compatibility. This study presents the first example of three-component asymmetric acyclic 1,3-difunctionalization with in situ-formed vinyl metal carbenes.
Article
Chemistry, Multidisciplinary
Jian Ji, Zongjing Hu, Cong Guan, Jinhua Liu, Yaqi Deng, Xuwen Chen, Shunying Liu
Summary: An efficient method for the 1,2-carbotriazolization of alkenes with N-sulfonyl-1,2,3-triazoles and aldehydes has been developed using a copper-catalyzed radical relay process. This strategy enables the production of beta-triazolized ketones with high regio- and chemoselectivity, and has a wide substrate scope. The resulting beta-triazolized ketone scaffold shows promising inhibitory activity on osteosarcoma cell lines, making it a potential pharmacophore for drug discovery.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Maoqing Shi, Gejun Niu, Tianyuan Zhang, Aimin Xu, Rimei Zheng, Abdulla Yusuf, Taoda Shi, Wenhao Hu, Yu Qian
Summary: A novel pyrazole migration and cycloaddition process was developed using AgOTf-catalyzed annulation reactions of α-diazo pyrazoleamides with ketimines. This protocol provides an efficient approach to synthesize a series of spirooxindole-based β-lactams with good to excellent yields, and the diastereoselectivity can be switched by tuning the substituents on the α-diazo pyrazoleamides.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Longlong Song, Lulu Xiong, Dan Ni, Weixiong Chen, Jian Ji, Jian Xue, Xuwen Chen, Xiang Wu, Xiao He, Shunying Liu
Summary: This study reports a [Pd(eta 3-C3H5)Cl]2/Sc(OTf)3 catalytic system accelerated by Brønsted acids for the selective aza-Michael addition of vinyl-substituted quinolines, diazos, and anilines/alcohols. The activation of the corresponding Lewis acid by the generation of anhydride analogues from Brønsted acid and the counter anion (OTf-) promotes nearly quantitative transformation. The triple co-catalytic system provides a strategy for the activation of vinylquinolines with a linear selectivity containing gamma-quaternary carbon.
Article
Chemistry, Organic
Ji Jian, Liu Jinhua, Guan Cong, Chen Xuwen, Zhao Yun, Liu Shunying
Summary: The green and efficient synthesis of N-2-substituted 1,2,3-triazoles was achieved by coupling cheap and easily available alcohols with N-sulfonyl-1,2,3-triazole using in-situ generated sulfonic acid as a catalyst. The reaction exhibited high regioselectivity and good yields without the need for additional catalysts or additives. Mechanistic studies suggested that the reaction was promoted by methanesulfonic acid (MsOH) generated from the hydrolysis of N-sulfonyl-1,2,3-triazoles, and high regioselectivity was achieved through a thermally stable intermediate.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yu Qian, Jie Tang, Xiaoyu Zhou, Jian Luo, Xiaoyan Yang, Zhuofeng Ke, Wenhao Hu
Summary: Multifunctionalization through the interception of active intermediates is an attractive strategy for the efficient synthesis of complex molecular structures. In this study, the first asymmetric trifunctionalization reactions with rhodium carbynoids were presented, allowing for the synthesis of a wide array of β-amino esters in high yields and exceptional enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Mengchu Zhang, Tianyuan Zhang, Sifan Yu, Huang Qiu, Abdulla Yusuf, Xinfang Xu, Yu Qian, Wenhao Hu
Summary: This paper describes an efficient ternary-catalytic multicomponent reaction for the rapid construction of 4-hydroxycoumarin derivatives. The potential utilities of the products as platform molecules are demonstrated through late-stage transformations and in vitro trial of antitumor activity.
Article
Chemistry, Organic
Zhengli Luo, Xuwen Chen, Jian Xue, Yaqi Deng, Suzhen Dong, Shunying Liu
Summary: A method has been developed for the rapid and efficient synthesis of benzosultams containing continuous quaternary carbons in a one-pot fashion, with moderate to excellent yields at room temperature. The resulting products exhibit good anticancer activity in osteosarcoma cells.
ORGANIC CHEMISTRY FRONTIERS
(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)