Article
Chemistry, Organic
Seonghyeon Nam, Ikyon Kim
Summary: A modular approach was used to successfully synthesize a polyfunctionalized indolizine-indole fused system, using readily available compounds and a combination of a one pot three-component assembly and Cu-catalyzed double C-N coupling reactions. This method allows for the formation of multiple new bonds in a simple and efficient manner.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dake Song, Yi Qin, Ying Liu, Jifan Wang, Haijie Yang, Zhonghui Zheng, Feng Xu, Xuefei Bao, Guoliang Chen
Summary: The immobilization of ciprofloxacin on chloromethyl polystyrene resin as a recyclable ligand for copper-catalyzed coupling reactions of (hetero)aryl halides and amines provides excellent results. The ligand is easily recovered and reused without loss of catalytic ability, and is environmentally friendly with no detectable ciprofloxacin in the reaction solution. Important structural units for the pharmaceutical and chemical industries can be assembled using this method.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Regina M. Oechsner, Ivo H. Lindenmaier, Ivana Fleischer
Summary: We present a nickel catalyzed C-S cross-coupling reaction of aryl and alkenyl triflates with alkyl thiols. By using an air-stable nickel precatalyst, various thioethers could be synthesized under mild reaction conditions within a short reaction time. The reaction demonstrated a broad substrate scope, including pharmaceutically relevant compounds.
Article
Chemistry, Organic
Yong-Chua Teo, Yun-Ru Tan, M. Kyra Saanvi, Chu-Ken Loh, Swee-Ngin Tan
Summary: A practical strategy for the C-N cross-coupling of aliphatic and aromatic sulfonamides with substituted aryl bromides is reported. The optimized conditions resulted in good to excellent yields (up to 78%) of N-arylated products under ligand-free conditions.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Subarna Pan, Suparna Kundu, Rajarshi Samanta
Summary: This article describes a simple and efficient method for the synthesis of N-arylated 2-pyridone derivatives catalyzed by Rh(II), using 2-oxypyridine and diazonaphthoquinone as coupling partners. The reaction involves the insertion of the nitrogen atom of the 2-oxypyridine derivative into quinoid carbene and subsequent 1,6-benzoyl migratory rearrangement. The reaction exhibits broad scope and has the potential to provide axially chiral N-arylated 2-pyridone derivatives under suitable asymmetric conditions.
Article
Chemistry, Organic
Di-Xiang Bai, Rachel Sin-Ee Lim, Hui-Fen Ng, Yong-Chua Teo
Summary: This paper presents a simple and efficient strategy for the C-N cross-coupling of indazole with various substituted aryl bromides. The optimized conditions allow for the synthesis of a wide range of N-arylated products in good to excellent yields (up to 87%) under ligand-free conditions.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Mei Wu, Nancheng Lian, Cuimin Wu, Xinyao Wu, Houzheng Chen, Chen Lin, Sunying Zhou, Fang Ke
Summary: A new reaction between aromatic hydrazines and quinoxalines has been developed using a photocatalytic system. This method allows for the coupling of the C(sp(2))-C(sp(2)) bond through C(sp(2))-N bond cleavage and direct C(sp(2))-H functionalization. Mechanistic studies reveal the importance of a benzene radical generated via oxidative cleavage of the aromatic hydrazines in the presence of a photocatalyst. This process is compatible with various functional groups and provides convenient access to 3-arylquinoxalin-2(1H)-ones.
Article
Chemistry, Physical
Bao Song, Ningtao Cao, Jie Zhang, Jianwei Xie
Summary: A facile method using copper pyrithione (CuPT) as the catalyst was described for the synthesis of N-arylheterocycles and di(hetero)aryl sulfides under mild conditions. The reactions showed high yields and broad substrate tolerance, with CuPT serving as the copper catalyst for CN coupling and as a catalyst and coupled partner for CS coupling. The S-arylation process was also utilized for the construction of valuable bioactive 2-sulfonylpyridine 1-oxide derivatives.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Organic
Patrick Cyr, Eve-Marline Joseph-Valcin, Patrick Boissarie, Bruno Simoneau, Anne Marinier
Summary: This study presents a copper-catalyzed method for the N-1-selective arylation of 3-aminoindazoles using readily accessible aryl bromides as coupling partners, facilitating the synthesis of a variety of substituted 3-aminoindazoles. The methodology was also applied to other aminoazoles of interest to the pharmaceutical industry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Robert D. Riley, Blake S. N. Huchenski, Karlee L. Bamford, Alexander W. H. Speed
Summary: This study demonstrates that diazaphospholene hydrides can be regenerated by the combination of phenylsilane and alkali metal salts, enabling catalytic radical reactions of aryl iodides. The method is not only applicable to aryl iodides, but can also be extended to aryl bromides, which benefit from visible light irradiation. Additionally, intermolecular radical hydroarylation reactions with arenes, thiophenes, and a pyridine have been successfully achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yaling Huang, Zisong Qi, Xingwei Li
Summary: This study presents a rhodium-catalyzed highly enantioselective reaction, which enables the access to functionalized indoles with excellent enantioselectivities through the nucleophilic cyclization of 2-alkynylanilines.
Article
Chemistry, Organic
Shuai Yang, Yanghui Zhang
Summary: Alkene-relayed C-H activation is a promising strategy for selective functionalization of C-H bonds. We have developed a Pd-catalyzed annulation reaction of 2-iodobiphenyls with maleimides as a relay for C-H alkylation. This reaction demonstrates broad substrate scope and high efficiency, providing a straightforward method for the synthesis of succinimide-fused 9,10-dihydrophenanthrenes. Additionally, a reaction utilizing acenaphthylene as the relay has been developed, enabling easy access to dibenzo[j,l]fluoranthenes.
Article
Chemistry, Organic
Shuai Yang, Yanghui Zhang
Summary: Alkene-relayed C-H activation is a novel strategy for selectively functionalizing C-H bonds. In this study, we developed a Pd-catalyzed annulation reaction using 2-iodobiphenyls and maleimides as a relay for C-H alkylation. The reaction exhibited a broad substrate scope and high efficiency, providing a straightforward method for synthesizing succinimide-fused 9,10-dihydrophenanthrenes. Additionally, we also developed a reaction using acenaphthylene as the relay, allowing easy access to dibenzo[j,l]fluoranthenes.
Article
Chemistry, Organic
Che-Ming Hsu, Shao-Chi Lee, Hao-En Tsai, Yong-Ting Tsao, Cheng-Lin Chan, Shinje Minoza, Zong-Nan Tsai, Li-Yun Li, Hsuan-Hung Liao
Summary: In this study, we successfully activated the C-S bond in sp(3)-hybridized thiols by introducing a per-/polyfluoroaryl moiety, enabling the efficient removal of sulfur groups and the generation of aliphatic radicals that can react with aryl halides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Gana Sanil, Maciej Krzeszewski, Wojciech Chaladaj, Witold Danikiewicz, Iryna Knysh, Lukasz Dobrzycki, Olga Staszewska-Krajewska, Michal K. Cyranski, Denis Jacquemin, Daniel T. Gryko
Summary: This study presents the tandem intramolecular hydroarylation of alkynes accompanied by a 1,2-aryl shift. By utilizing the unique electron-rich character of the 1,4-dihydropyrrolo[3,2-b]pyrrole scaffold, pi-expanded, centrosymmetric pyrrolo[3,2-b]pyrroles were synthesized by reacting alkynes at the already occupied positions 2 and 5. The reaction only proceeds in the presence of cationic gold catalyst and produces unknown compounds with six conjugated rings. These synthesized compounds have potential applications in the creation of new materials with various functionalities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)