Article
Chemistry, Physical
Shrikant M. Khake, Naoto Chatani
Summary: The Rh(III)-catalyzed reaction of aniline derivatives containing a pyrimidine directing group with vinylsilanes leads to the formation of C3-substituted indoline derivatives via a highly regioselective C-H activation/alkene cyclization cascade. Mechanistic experiments suggest that C-H bond cleavage is not the rate-determining step, but rather the reaction proceeds through the formation of a six-membered rhodacycle as a key catalytic species via pyrimidine-directed electrophilic ortho-C-H rhodation.
Article
Chemistry, Organic
Lijun Shi, Mingshan Wen, Fuwei Li
Summary: An efficient synthesis of amino-substituted isoquinolines was achieved through Rh(III)-catalyzed oxidative [2+2+2] annulation, which was cooperatively enabled by a directing carbonyl and steric hindrance adjacent to the amino group of the pyridine. This C-H activation strategy also opens up possibilities for other oxidative transformations of heterocyclic C-H bonds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Qi-Liang Yang, Yi-Rui Luo, Rong-Yi Xu, Bei-Ning Zhang, Yan-Ni Zhang, Hai-Ming Guo
Summary: A sustainable pathway for the synthesis of tetracyclic purinium salts via ruthenium-catalyzed electro-oxidative annulation of C-6-arylpurine nucleosides with alkynes without a stoichiometric metal oxidant has been developed. The protocol exhibits high regioselectivity, broad scope, and wide functional group tolerance, allowing efficient coupling of various biologically important molecules. A novel purinoisoquinolinium-coordinated ruthenium(0) sandwich intermediate has been isolated, crystallographically characterized, and electrochemically analyzed, offering direct mechanistic insight.
Article
Chemistry, Organic
Jiaqi Zhang, Weijie Xu, Weihui Zhuang, Ximan Chen, Xiaofeng Zhang, Qiufeng Huang
Summary: In this study, a rhodaelectro-catalyzed C2-H selectively decarboxylative alkenylation of 3-carboxy-1H-indoles using electricity as the traceless terminal oxidant has been achieved. The weakly coordinating carboxyl group serves as the traceless directing groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Min Liu, Kelu Yan, Jiangwei Wen, Xue Li, Xiaoyu Wang, Fengjie Lu, Xiu Wang, Hua Wang
Summary: The rhodium(III)-catalyzed C-H/diazo coupling and tandem annulation of 3-oxopent-4-enenitriles have been proposed for the synthesis of polysubstituted phenols, yielding most products in good yields. Preliminary mechanistic studies and derivatization reactions of phenol products were also conducted, offering an alternative approach for synthesizing a variety of useful phenols.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Gao Huang, Jin-Tao Yu, Changduo Pan
Summary: A rhodium-catalyzed C-H activation/annulation of N-aryl-pyrazolidinones with vinylene carbonate was developed, leading to the successful construction of non-substituted 5,6-pyrazolo[1,2-a]cinnoline derivatives. This method provides an efficient and selective approach to synthesizing these derivatives, which are challenging to obtain using other procedures. Importantly, the protocol does not require external oxidants and generates water and carbon dioxide as clean by-products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jakub Brzeskiewicz, Rafal Loska
Summary: The palladium-catalyzed C(sp2)-H functionalization of bromoaryl aldonitrones leading to benzocyclobutenone-derived ketonitrones is described, allowing for the preparation of a wide range of strained, four-membered ketonitrones with broad functional group tolerance. Downstream transformations of the formed products were demonstrated, illustrating the synthetic utility of the obtained benzocyclobutenone-derived nitrones for the construction of polycyclic nitrogen-containing scaffolds.
Article
Chemistry, Applied
Eswaran Kamaraj, Prasanta Roy, Yong Rok Lee
Summary: A rhodium-catalyzed [5+1] cycloaddition through C-H activation/O-annulation strategy is described for synthesizing biologically interesting isochromenes. This method selectively provides divergently functionalized isochromenes containing spirosuccinimide and maleimide scaffolds based on the maleimides and itaconimides used as substrates. It demonstrates a broad substrate scope, remarkable functional group tolerance, and high regioselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Multidisciplinary Sciences
Yi-Kang Xing, Xin-Ran Chen, Qi-Liang Yang, Shuo-Qing Zhang, Hai-Ming Guo, Xin Hong, Tian-Sheng Mei
Summary: Alpha-pyridones and alpha-pyrones are common structural motifs in natural products and biologically active compounds. This study reports an oxidant-free Rh-catalyzed electrochemical vinylic C-H annulation of acrylamides with alkynes, providing alpha-pyridones and cyclic imidates through divergent pathways with excellent regioselectivities.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Md Raja Sk, Arya Bhattacharyya, Shuvendu Saha, Arpita Brahma, Modhu Sudan Maji
Summary: Annulative pi-extension (APEX) reaction is a precise synthesis method for polycyclic aromatic hydrocarbons (PAHs) such as nanographene and graphene. In this study, a masked bay-region APEX reaction was successfully used to efficiently synthesize valuable PAH pyrene with substitutions at the challenging K-region. The reaction involved Rh-III-catalyzed C-H activation, alkyne-insertion, intramolecular nucleophilic attack, dehydration, and aromatization steps.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Smruti Ranjan Mohanty, Namrata Prusty, Tanmayee Nanda, Shyam Kumar Banjare, Ponneri C. Ravikumar
Summary: In this study, the ruthenium-catalyzed regioselective sp2(C-H) monoalkenylation of N-arylpyridones was demonstrated, where the pyridone served as a weakly coordinating directing group. Importantly, this methodology was effectively applied to the synthesis of various drug analogues, with high yields up to 93%. HRMS analysis also revealed the presence of a six-membered ruthenium complex.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Qiang-Qiang Li, Yosuke Hamamoto, Cheryl Cai Hui Tan, Hiroyasu Sato, Shingo Ito
Summary: A new synthetic approach to pi-extended imidazolium salts has been developed, which involves the 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with imidoyl chlorides. The addition of cesium fluoride as an additive is crucial for the successful conversion. Experimental and theoretical studies show that this cycloaddition proceeds via a stepwise mechanism. This method provides an efficient way to synthesize various imidazolium-containing polycyclic aromatic compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Quannan Wang, Yu-Han Nie, Chen-Xu Liu, Wen-Wen Zhang, Zhi-Jie Wu, Qing Gu, Chao Zheng, Shu-Li You
Summary: In this study, an enantioselective C-H activation/annulation reaction catalyzed by CpRh(III) was reported for the efficient synthesis of planar chiral ferrocene-fused heterocyclic molecules. By finding suitable catalysts, products with high yields and excellent enantioselectivity were obtained. The proposed reaction mechanism was supported by experimental and computational studies.
Article
Chemistry, Organic
Jian Lin, Liuyu Hu, Chao Chen, Huijin Feng, Yang Yu, Yaxi Yang, Bing Zhou
Summary: A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed for the efficient synthesis of varied thiobenzofurans in a straightforward manner. This protocol demonstrates good functional group tolerance and broad substrate scope under mild reaction conditions.
Article
Chemistry, Organic
Xiaoting Gan, Fen Huang, Zhijun Ren, Bo Li, Shaojie Chen, Wenkun Luo, Jun Zhou
Summary: The synthesis of multi-substituted 1-aminoisoquinolines from aminopyridine pivalamides with alkynes by Rh(III)-catalyzed C-H activation coupling has been successfully achieved. This method is tolerant of various functional groups and provides moderate yields of highly substituted isoquinoline derivatives.
TETRAHEDRON LETTERS
(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)