Article
Chemistry, Organic
Miyuki Yamaguchi, Ryoya Hagiwara, Hana Muto, Kanami Gayama, Hideyuki Konishi, Kei Manabe
Summary: A palladium-dihydroxyterphenylphosphine catalyst was used for the selective C3-arylation of tryptamine derivatives with aryl nonaflates, leading to the formation of C3a-arylated pyrroloindolines via intramolecular cyclization. Complex formation between the lithium salts of DHTP and the tryptamine derivative is proposed as the key factor for promoting arylation at the C3-position of the indole ring. Additionally, C4a-arylated pyridoindolines were obtained by reactions using homotryptamine derivatives.
Article
Chemistry, Organic
Meng-Lan Luo, Qiumeng Hou, Shuai-Jiang Liu, Qian Zhao, Rui Qin, Cheng Peng, Bo Han, Gu Zhan
Summary: In this study, a straightforward and efficient method for the synthesis of tetracyclic hydropyrrolo-[3,2-b]indole scaffolds was developed through a cascade reaction of oxindole-derived nitrones with allenoates. Multiple bond formations and cleavage could be achieved using a simple catalyst under mild conditions.
Article
Chemistry, Organic
Dharmendra Kumar, Dhananjay Chaudhary, Km Ishu, Suman Yadav, Naveen Kumar Maurya, Ruchir Kant, Malleswara Rao Kuram
Summary: A domino reaction sequence has been developed for the synthesis of pyrroloindolines, in which tryptamine derivatives and donor-acceptor diazo compounds are used as substrates. This reaction simultaneously forms three consecutive stereogenic centers, providing a convenient and efficient strategy for the construction of complex molecules. Copper catalysis enables the reaction to proceed smoothly at room temperature, and a wide range of substrates can be employed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xu-Yang Hu, Hai-Feng Xu, Qiang Chen, You-Lu Pan, Jian-Zhong Chen
Summary: In this study, a novel synthesis method was developed for the indolo[2,1-alpha]isoquinoline core structure under air environment, resulting in the successful synthesis of various valuable derivatives with good yields. A radical pathway was proposed to explain the experimental results.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
LinLin Ren, Yonggong Wang, Yanman Huo, Xiaogang Tong, Chengfeng Xia
Summary: A visible-light-induced radical cascade reaction was developed for the direct alkynylation of tryptamines with alkynyl sulfones, resulting in a series of high-yield C3-alkynyl pyrroloindolines. This method offers readily available substrates, good functional group tolerability, and scalability. C3-alkynyl pyrroloindolines show great potential as useful building blocks in the preparation of complex and valuable pyrroloindoline alkaloids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Shaomin Chen, Zhiyan Chen, Tianjian Zhang, Bo Zhao, Bo You, Minghao Li, Yanlong Gu
Summary: An efficient acid-catalyzed three-component cascade strategy was established to synthesize phenyl-substituted dihydrocyclohepta[b]indole carboxylate, which is a privileged scaffold. Another route to access tetrahydrocyclohepta[b]indoles was also discovered. These methods are practically attractive due to readily available materials, inexpensive metal-free catalysts, eco-friendly solvents, and divergent synthesis.
Article
Chemistry, Multidisciplinary
Xiaoyu Liu, Kun He, Na Gao, Peiyun Jiang, Jun Lin, Yi Jin
Summary: A new radical-mediated, one-pot, multicomponent cascade reaction was developed for the synthesis of azide-biindole derivatives. Mechanistic studies showed the formation of nitrogen-centred free radicals which initiated the cascade reaction to obtain the final products. This methodology may have potential applications in constructing other azido heterocycles.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Wan Tang, Duan-Yang Yan, Kai-Cheng Liang, Ma Su, Feng Liu
Summary: We report a mild protocol for the synthesis of diverse indoline-fused heterocycles via a photoredox catalysis reaction. The reaction proceeds through a cascade of radical processes and exhibits wide functional-group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Raju Chouhan, Arup Jyoti Das, Sajal Kumar Das
Summary: The study demonstrates the first examples of pyrrole-intercepted dearomative indole C3-allylation and benzylation of indole-tethered pyrroles for the synthesis of 2,3-cis-fused tetracyclic indolines. By directing the intermolecular alkylation to occur at the indole C3 position and utilizing the high nucleophilicity of the pyrrole template, the cascade reaction achieved broad substrate scope, excellent yields, and high selectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Raju Chouhan, Arup Jyoti Das, Sajal Kumar Das
Summary: This study describes a novel chemical reaction strategy to synthesize 2,3-cis-fused tetracyclic indolines by utilizing a cascade reaction between indole and pyrrole. The reaction exhibits high selectivity and broad substrate applicability, providing new insights and methods for organic synthesis research.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Thomas Varlet, Damien Bouchet, Elsa Van Elslande, Geraldine Masson
Summary: A convenient and scalable dearomative hydroacylation reaction of indoles is reported. Using readily available aldehydes as acyl sources and TBADT as an inexpensive direct HAT photocatalyst, various indole derivatives are converted into synthetically interesting 2-acylindolines with good yields and diastereoselectivity under mild conditions. An asymmetric version of the reaction is successfully developed, and an experimental mechanistic investigation provides further insights into the assumed reaction pathway.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Qian Wan, Jia-Hao Xie, Chao Zheng, Yao-Feng Yuan, Shu-Li You
Summary: In this study, a catalytic asymmetric dearomatization reaction of electron-deficient heteroarenes with alpha-substituted isocyanoacetates was reported, leading to a range of optically active pyrrolo[3,4-b]indole derivatives. The reaction yielded good results with high stereoselectivities, using a catalytic system consisting of a cinchona-derived amino-phosphine and silver oxide. This method features wide substrate scope, mild conditions, and provides a new strategy for developing asymmetric dearomatization reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Carlos Lazaro-Milla, Hikaru Yanai, Pedro Almendros
Summary: A new sequential cyclization cascade method has been successfully developed in this study for the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters.
Article
Chemistry, Organic
Xiao-Yong Duan, Zhaohui Tian, Binghao Liu, Tao He, Liang-Liang Zhao, Mengdie Dong, Pengna Zhang, Jing Qi
Summary: This work describes the NHC-catalyzed Michael/Mannich/lactamization cascade reaction of enals with either indole-2-carboxaldehyde-derived aldimines or indole-7-carboxaldehyde-derived aldimines, allowing for the rapid assembly of optically active pyrroloindolones and pyrroloquinolinones derivatives under mild conditions with high yields, excellent enantioselectivities, and a broad substrate scope.
Article
Chemistry, Organic
Xiaohu Zhao, Yuqiao Zhou, Bao-Lin Li, Guangxi Du, Zhipeng Yu
Summary: A highly efficient and catalyst-free method has been developed for the dearomatization of 3-(2-isocyanoethyl)indoles using in situ generated nitrile imines. This method involves a nucleophilic/Friedel-Crafts/aza-Mannich type cascade and 1,3-dipolar cycloaddition reaction, and allows for the rapid assembly of a wide range of polycyclic indoline scaffolds with moderate to excellent yields and diastereoselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Xuefeng Tan, Shuang Gao, Weijun Zeng, Shan Xin, Qin Yin, Xumu Zhang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Multidisciplinary
Gen-Qian Chen, Bi-Jin Lin, Jia-Ming Huang, Ling-Yu Zhao, Qi-Shu Chen, Shi-Peng Jia, Qin Yin, Xumu Zhang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Organic
Le'an Hu, Yao Zhang, Gen-Qiang Chen, Bi-Jin Lin, Qing-Wen Zhang, Qin Yin, Xumu Zhan
Article
Chemistry, Multidisciplinary
Le'an Hu, Yao Zhang, Qing-Wen Zhang, Qin Yin, Xumu Zhang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Yongjie Shi, Xuefeng Tan, Shuang Gao, Yao Zhang, Jingxin Wang, Xumu Zhang, Qin Yin
Article
Chemistry, Organic
Yao Zhang, Yun-Qi Liu, Le'an Hu, Xumu Zhang, Qin Yin
Article
Chemistry, Organic
Yongjie Shi, Jingxin Wang, Qin Yin, Xumu Zhang, Pauline Chiu
Summary: An asymmetric 1,2-reduction of cyclic alpha,beta-unsaturated ketones was achieved under mild conditions, catalyzed by in situ generated copper hydride ligated with (R)-DTBM-C-3*-TunePhos. The reaction produced various enantiomerically enriched cyclic allylic alcohols, with up to 98% ee enantioselectivities for alpha-brominated cydoalkenones and moderate enantioselectivities for substrates without alpha-substituents.
Article
Chemistry, Organic
Congcong Yin, Yingmin Pan, Xumu Zhang, Qin Yin
Summary: An unprecedented Rh-catalyzed asymmetric and diastereoselective hydrogenation method for easily accessible α,β-disubstituted unsaturated lactams was reported. This method provides synthetically valuable chiral lactams with 1,2-consecutive stereocenters. The reaction can be performed on a gram scale and the products can be transformed into enantiomerically pure trans-3,4-disubstituted piperidines, which are prevalent structural units in medicinal agents.
Article
Chemistry, Organic
Ke-Qin Wu, Hui Li, Ao Zhou, Wei-Ran Yang, Qin Yin
Summary: A Pd-catalyzed regioselective C-H bond allylic alkylation of phenols with 1,3-dienes is reported, which selectively functionalizes the ortho C-H bond of 2-naphthols, 1-naphthols, and electron-rich phenols to synthesize phenol derivatives with diverse structures. The reaction is accelerated by a diphosphine ligand, does not require any other additive, and exhibits broad substrate scope and good chemo- and regioselectivity. Additionally, an asymmetric variant is investigated, achieving product with up to 55% enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Yongjie Shi, Nianxin Rong, Xumu Zhang, Qin Yin
Summary: Chiral primary amines are important in drug synthesis and metal-catalyzed enantioselective reductive amination provides a direct method for their synthesis. However, progress in this field has been slow due to challenges such as reversible formation of unstable intermediates and lack of efficient catalytic systems. While the synthesis of certain substrate types like alpha-keto esters/amides is well-established, enantioselective control in other substrates remains unsolved.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Applied
Lei Xu, Gang Wang, Nianxin Rong, Yang Gu, Le'an Hu, Hengzhi You, Qin Yin
Summary: A one-step and highly enantioselective synthesis of (R)-2-(1-aminoethyl)-4-fluorophenol((R)-I) was developed as a key chiral intermediate for the preparation of the tyrosine kinase inhibitor repotrectinib. The reaction was carried out using a Ru-catalyzed asymmetric reductive amination with NH4OAc as the nitrogen source and H-2 as the reducing agent. The use of a continuous-flow reactor enabled higher reaction efficiency and eliminated the need for column chromatography for product purification, making it a cost-effective alternative strategy for production of repotrectinib.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Organic
Zengjin Dai, Ying-Min Pan, Shou-Guo Wang, Xumu Zhang, Qin Yin
Summary: A series of half-sandwich Ir(iii) complexes were synthesized and applied to catalyze the Leuckart-Wallach reaction to produce racemic alpha-chiral primary amines. Despite attempts at asymmetric transformation, the enantio-selectivity achieved was limited, but the study provides a basis for further efforts in developing better chiral catalysts for this important transformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Yingying Tian, Le'an Hu, Yuan-Zheng Wang, Xumu Zhang, Qin Yin
Summary: Transition-metal-catalysed asymmetric reductive amination is a direct method for accessing chiral amines, converting carbonyl compounds and ammonia or amines into drug-relevant compounds in one pot. Recent progress has been made in homogeneous transition-metal-catalysed ARA reactions with H-2 or other hydride sources, but challenges and potential still exist in this field.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Qin Yin, Yongjie Shi, Jingxin Wang, Xumu Zhang
CHEMICAL SOCIETY REVIEWS
(2020)
Article
Chemistry, Multidisciplinary
Tao Yang, Xiaochong Guo, Qin Yin, Xumu Zhang
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)
