Review
Chemistry, Physical
Marta Papis, Francesca Foschi, Sara Colombo, Egle Maria Beccalli, Camilla Loro, Gianluigi Broggini
Summary: The combination of copper catalysts and hypervalent iodine reagents is a versatile tool in organic synthesis for the functionalization of unactivated substrates, allowing access to various classes of compounds.
Article
Chemistry, Multidisciplinary
Illia Lenko, Alexander Mamontov, Carole Alayrac, Remi Legay, Bernhard Witulski
Summary: The research demonstrates the divergent Pd-catalyzed reaction cascades with various 1,3-diynamides, leading to different products depending on the presence or absence of TBAF. Furthermore, deuterium labeling experiments reveal the unique formation mechanism of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Editorial Material
Chemistry, Multidisciplinary
Ahmed Fnaiche, Bianca Bueno, Claire L. McMullin, Alexandre Gagnon
Summary: In this study, we investigated the Barton copper-promoted C3-arylation of indoles using triarylbismuth bis(trifluoroacetates) in detail. Under Barton's conditions, the arylation of unsubstituted 1H-indole gave low yield of C3-arylated indole, along with small amounts of double C2/C3-arylation product and traces of C2 arylation product. On the contrary, the arylation of indoles blocked at the C2 position was highly efficient and provided desired products of C3-arylation in good to excellent yields. The reaction showed simple conditions, good substrate scope, excellent functional group compatibility, and allowed the transfer of electron-neutral or deficient aryl groups. Computational studies proposed a mechanism involving a trifluoroacetate-assisted C-H activation step.
Article
Chemistry, Multidisciplinary
Ahmed Fnaiche, Bianca Bueno, Claire L. McMullin, Alexandre Gagnon
Summary: In this study, we investigated the C3-arylation of indoles using triarylbismuth bis(trifluoroacetates) promoted by Barton's copper. The arylation of unsubstituted 1H-indole under Barton's conditions yielded a low yield of C3-arylated indole, along with some double C2/C3-arylation product and traces of C2 arylation product. On the other hand, the arylation of C2-blocked indoles showed high efficiency and good to excellent yields of the desired C3-arylation products. The reaction demonstrated simple conditions, broad substrate scope, excellent functional group compatibility, and the ability to transfer electron-neutral or deficient aryl groups. Computational studies proposed a mechanism involving trifluoroacetate-assisted C-H activation.
Article
Chemistry, Multidisciplinary
Jun Kee Cheng, Bin Tan
Summary: This article introduces the wide applications and importance of indole compounds in designing new axially chiral scaffolds. The rich reactivity and N-H functionality of indole compounds allow chemical derivatization for enhanced medicinal, material, and catalytic properties. The research group successfully synthesized chiral biaryl compounds through the design of novel organocatalytic arylation reactions. Indole compounds showed reliable reactivity with azoarenes, nitrosonapthalenes, and quinone derivatives, which, in combination with chiral phosphoric acid catalyst, enabled excellent control of stereo-, chemo-, and regioselectivity to furnish diverse scaffolds. Additionally, indole compounds can also act as nucleophiles in the desymmetrization of 1,2,4-triazole-3,5-diones. This account provides a succinct illustration of these developments.
Article
Chemistry, Organic
Raktim Abha Saikia, Dhiraj Barman, Anurag Dutta, Ashim Jyoti Thakur
Summary: The translation article describes a Copper(I)-catalyzed method for N-arylation of hydantoins using diaryliodonium salts as aryl partners. This method is efficient under mild reaction conditions, delivering a variety of functionalized N-3-arylated products, and can also be applied for the synthesis of chiral hydantoins.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shutao Wang, Yanjie Ye, Yansong Hu, Xu Meng, Zhao Liu, Jiyu Liu, Kuan Chen, Zhengze Zhang, Yuan Zhang
Summary: This article presents a Ce(iii)-catalyzed, visible-light-induced aerobic oxidative dehydrogenative coupling/aromatization reaction between glycine derivatives and alkenes, providing an efficient method for synthesizing quinoline derivatives and post-modifying oligopeptides containing glycine residues under mild conditions, without the need for external photosensitizers.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Ji-Wei Zhang, Shao-Hua Xiang, Shaoyu Li, Bin Tan
Summary: The article presents an efficient synthetic route to access important atropisomers with biaryl frameworks through copper-catalyzed reactions, featuring mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.
Article
Chemistry, Organic
Igor Beckers, Galahad O'Rourke, Dirk De Vos
Summary: This study reports a regiospecific C-H arylation of a highly functionalized azepino[5,3,4-cd]indole scaffold lacking directing groups via Pd(II) and Cu(II) co-catalysis, which offers a promising method to surpass the limitations of traditional protecting groups or metal additives in late-stage C-H activation reactions. The direct C-H coupling was demonstrated in the convergent synthesis of the FDA approved anticancer drug rucaparib.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Axel Sabourin, Jeremy Dufour, Jean-Pierre Vors, David Bernier, Jean-Luc Montchamp
Summary: This study presents the synthesis of N- and C-substituted benzophostams. N-substitution was achieved by alkylation using a heterocycle, LiHMDS, and alkyl halide, or by copper-catalyzed cyclization of N-alkyl phosphonamide. N-Arylation could be accomplished either on the preformed heterocycle or on the phosphonamide precursor via copper-catalyzed cross-coupling. Dimethylation at the benzylic position was conducted using LiHMDS and methyl iodide, or a palladium-catalyzed reductive Heck reaction as a cost-effective and efficient alternative.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Dingyi Wang, Xiangyang Chen, Jonathan J. Wong, Liqun Jin, Mingjie Li, Yue Zhao, K. N. Houk, Zhuangzhi Shi
Summary: This study presents a regioselective C7-H silylation of indole derivatives assisted by strong coordination of the palladium catalyst with a phosphorus directing group. The method allows for the effective synthesis of various C7-silylated indoles with broad functional group compatibility. Additionally, the hypothesis regarding the P(III)-directed C-H metalation event is successfully tested through mechanistic experiments and DFT calculations.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Liangbin Yu, Junjun Liu, Shiyu Xiang, Taotao Lu, Ping Ma, Qingyang Zhao
Summary: By using a chiral silver phosphate catalyst, a direct 5-endo-dig nucleophilic cyclization of 2-alkynylanilins was achieved under mild conditions, leading to the synthesis of various C-C axially chiral 2arylindoles with high yields and enantioselectivities. Control experiments showed the cooperative catalysis of AgOAc and chiral phosphoric acid, with the former accelerating the desired transformation and the latter improving enantioselectivity. Additionally, the synthetic applications and thermal stability of the products were investigated, making it the first example of silver-catalyzed enantioselective de novo synthesis of C-C axially chiral indole skeletons.
Article
Chemistry, Multidisciplinary
Peng Zhang, Qi Xu, Xiao-Mei Wang, Jia Feng, Chuan-Jun Lu, Yingzi Li, Ren-Rong Liu
Summary: The first enantioselective synthesis of N-N bisindole atropisomers via palladium-catalyzed construction of one indole skeleton is reported in this study. A wide variety of N-N axially chiral bisindoles were generated with good yields and excellent enantioselectivities through a cascade condensation/N-arylation reaction. The reaction mechanism and enantiocontrol were further investigated using density functional theory (DFT) calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Dan Wang, Zhaohua Wan, Heng Zhang, Hesham Alhumade, Hong Yi, Aiwen Lei
Summary: A novel electrochemical reductive arylation method was developed for the efficient synthesis of various diarylamines without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell, and several derivatization reactions were successfully carried out. Cyclic voltammetry experiments and mechanism studies revealed the roles of acetonitrile, formic acid, and triethyl phosphite in promoting this reductive arylation transformation.
Article
Chemistry, Physical
Jessica Rodriguez, David Vesseur, Alexis Tabey, Sonia Mallet-Ladeira, Karinne Miqueu, Didier Bourissou
Summary: A (MeDalphos)AuCI complex has been discovered to efficiently catalyze the cross-coupling reaction of indoles and allyl acetates/alcohols. The reaction tolerates various functional groups and selectively produces branched C3-allylated products. It utilizes the hemilabile character of the P<^>N ligand.
Article
Chemistry, Multidisciplinary
Chuan Liu, Qin Yin, Li-Xin Dai, Shu-Li You
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Chuan Liu, Ji-Cheng Yi, Xiao-Wei Liang, Ren-Qi Xu, Li-Xin Dai, Shu-Li You
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Organic
Chuan Liu, Qiu Wang
Article
Chemistry, Organic
Chuan Liu, Ji-Cheng Yi, Li-Xin Dai, Shu-Li You
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Long Han, Chuan Liu, Wei Zhang, Xiao-Xin Shi, Shu-Li You
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Organic
Min-Qiang Jia, Chuan Liu, Shu-Li You
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
Chuan Liu, Wei Zhang, Li-Xin Dai, Shu-Li You
ORGANIC & BIOMOLECULAR CHEMISTRY
(2012)
Article
Chemistry, Organic
Quan Cai, Chuan Liu, Xiao-Wei Liang, Shu-Li You
Article
Chemistry, Organic
Chuan Liu, Wei Zhang, Li-Xin Dai, Shu-Li You
Article
Chemistry, Organic
Run-Duo Gao, Chuan Liu, Li-Xin Dai, Wei Zhang, Shu-Li You
Article
Chemistry, Multidisciplinary
Xiao Zhang, Ze-Peng Yang, Chuan Liu, Shu-Li You
