Article
Chemistry, Applied
Dipak B. Deokar, Soumi Laha, B. Sridhar, Dharmendra Kumar Tiwari, Pravin R. Likhar
Summary: A palladium-catalyzed coupling reaction followed by dual annulation has been developed for the synthesis of various triazolo/pyrrolo fused benzofuro-quinolines from readily available starting materials. This method involves palladium-catalyzed Sonogashira coupling, benzan-nulation, and C-H activation triggered second annulation reaction cascades in a single pot. The polycyclic compound formed by this method consists of three different heterocyclic structures: benzofuran, quinoline, and triazole/pyrrole. The method provides a simple access to obtain a range of fused benzofurotriazalo/pyrroloquinolines in good to moderate yields.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chikkagundagal K. Mahesha, Sushma Naharwal, Narendra Dinkar Kharat, Sanjay K. Mandal, Rajeev Sakhuja
Summary: A tender-hearted Pd(II)-catalyzed C-H activation of 1-arylindazolones followed by an oxidative [4 + 2] annulation reaction has been successfully achieved, leading to the synthesis of cinnoline-fused indazolones with different regioisomeric forms. This reaction, carried out under mild and aerobic conditions without the use of any metal-oxidant, shows great potential.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Rita Ferro, Nuno Viduedo, A. Sofia Santos, Artur M. S. Silva, Beatriz Royo, M. Manuel B. Marques
Summary: A bimetallic synthesis method for 2-arylindoles from alcohols and anilines is presented, involving the dehydrogenation or oxidation of secondary alcohols using Ni or Mn catalysts, followed by conversion of the formed ketone into an imine intermediate and subsequent Pd-catalyzed oxidative cyclization to obtain the desired 2-arylindole. The intermediates generated were not isolated, allowing for the preparation of a series of 2-arylindoles. The compatibility of catalysts was explored, and the optimized protocol enables the integration of Earth-abundant metals and palladium complexes, enhancing the sustainability of N-heterocycle synthesis.
SYNTHESIS-STUTTGART
(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, Multidisciplinary
Fumitoshi Kakiuchi, Takuya Kochi
Summary: In this account, the authors discussed their efforts in palladium-catalyzed electrochemical C-H functionalizations, including C-H halogenations using different halogen sources, a one-pot synthesis method, and an iodine-mediated oxidative homo-coupling reaction of arylpyridines.
Article
Chemistry, Multidisciplinary
David Savary, Olivier Baudoin
Summary: C-H activation-based ring-forming methods are powerful for constructing complex molecular structures, especially useful for synthesizing chiral polycyclic aromatic hydrocarbons and other important organic electronic materials. A new enantioselective synthesis method using Pd-catalyzed C(sp(2))-H arylation protocol has been described, delivering diverse polycyclic compounds with high yield and good to excellent enantioselectivity, with investigation into their chiroptical properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Xin-Chen Zhan, Guo-Qiang Lin, Jian-Guo Fu, Xiao-Ming Ji, Shu-Sheng Zhang, Chen-Guo Feng
Summary: A cascade [4+3] annulation of o-alkenyl bromoarenes and o-bromoaniline derivatives is reported, leading to the synthesis of various dibenzo[b,f]azepines with substitutions on the 10/11 position in moderate to high yields. The versatility of this protocol is demonstrated through the preparation of a precursor for the drug molecule oxcarbazepine, gram-scale synthesis, and two product transformations. Unlike previous amination/Heck sequences, this cascade process follows a C(vinyl), C(aryl)-palladacycle involved pathway.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xiai Luo, Wenguang Li, Haiyan Lu, Guobo Deng, Yuan Yang, Chunming Yang, Yun Liang
Summary: This study achieved simultaneous C2-H arylation and C8-H alkylation of the naphthalene ring, providing an efficient method for synthesizing aryl-substituted spirocyclic oxindoles. The protocol enables three C-C bonds formation via intramolecular Heck reaction.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Ming-Shun Mei, Yanghui Zhang
Summary: A new approach for the synthesis of naphthalimides via a tandem reaction of o-methylbenzaldehydes and maleimides is developed in this work. The reaction involves Pd(II)-catalyzed benzylic C(sp(3))-H oxidation using an amino acid as the transient directing group and Diels-Alder reaction. The subsequent dehydration forms naphthalimides, allowing for easy access to a range of naphthalimides with a variety of substituents.
Article
Chemistry, Applied
Huan-Chang Hsiao, Pratheepkumar Annamalai, Jayachandran Jayakumar, Shang-You Sun, Shih-Ching Chuang
Summary: Novel dual-emissive and deep-blue/green fluorescent multi-substituted 4-azapyrenes with bathochromic shift emission, high quantum yields up to 0.60, and long excited-state lifetime were successfully synthesized by annulative pi-extension reactions, involving palladium-catalyzed dehydrogenative annulation and superacid-mediated cyclization.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Sujin Min, Taeeun Kim, Taejoo Jeong, Junhyeok Yang, Yebin Oh, Kyeongwon Moon, Amitava Rakshit, In Su Kim
Summary: The synthesis of functionalized carbazoles has become an important topic in drug discovery and material science. In this study, a rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones and 2-methylidene cyclic carbonate was disclosed, resulting in the formation of C2-formylated carbazoles. The synthetic utility of this protocol was demonstrated by various post-transformations of C2-formylated carbazoles.
Article
Chemistry, Organic
Xiaoqiang Lei, Juan Feng, Qinglan Guo, Yuanhe Li, Jiangong Shi
Summary: This study reports an unprecedented [2 + 3] annulation of N-sulfonyl-1,2,3-triazoles with enaminones, leading to the synthesis of polysubstituted furans. The use of Rh(II)-Bronsted acid as cooperative catalysts plays a crucial role in the success of the transformations. Unlike conventional annulations of N-sulfonyl-1,2,3-triazoles, the Rh(II)-azavinyl carbenes species serve dual functions in this work by cleaving the C(sp(2))-N bond.
Article
Chemistry, Applied
Mohammad Aslam, Shreedhar Devkota, Sana Jamshaid, Yong Rok Lee
Summary: A synthetic strategy for the installation of diversely functionalized quinones at the C4 position of indoles has been developed. This method provides a rapid and efficient route to a variety of 4-quinonylindoles and biologically interesting bis(indol-4-yl)quinones.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Chanyoung Maeng, Yongjoo Yun, Jeong-Yu Son, Phil Ho Lee
Summary: We have developed a simplified synthetic method for the selective preparation of monosubstituted alkenyl dihydroazulenolactones and their derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Quan-Zhe Li, Si-Hua Hou, Jun-Chen Kang, Peng-Fei Lian, Yu Hao, Chao Chen, Jia Zhou, Tong-Mei Ding, Shu-Yu Zhang
Summary: Bioinspired palladium-catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C-H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic olefin. The functionalized prolines were used as intermediates for the synthesis of several natural products: lucentamycin A, oxotomaymycin, oxoprothracarcin, and barmumycin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lei Li, Qiao Yang, Yuan Wang, Yanxing Jia
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Lei Li, Paruke Aibibula, Qianlan Jia, Yanxing Jia
Review
Chemistry, Multidisciplinary
Lei Li, Zhuang Chen, Xiwu Zhang, Yanxing Jia
Article
Chemistry, Organic
Lei Li, Weimin Hu, Yanxing Jia
Article
Chemistry, Multidisciplinary
Lei Li, Kuo Yuan, Qianlan Jia, Yanxing Jia
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Keyuan Li, Yuan Wang, Lijun Chen, Lei Li, Yanxing Jia
Summary: A green and regioselective electrooxidative coupling reaction was developed for the synthesis of benzofuro[3,2-b]indolines from indoles and phenols. A variety of benzofuro[3,2-b]indolines were prepared in moderate to excellent yields, and a plausible mechanism was proposed for the reaction.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Lei Li, Weida Liang, Mario E. Rivera, Ye-Cheng Wang, Mingji Dai
Summary: A concise synthesis of (-)-GA18 methyl ester from commercially available and cheap andrographolide is reported. The synthesis involves intramolecular ene reaction, oxidative cleavage and aldol condensation, photochemical cycloaddition, and skeletal rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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)