Article
Chemistry, Applied
Francisco Villalba, Ana C. Albeniz
Summary: The pyridone fragment in the ligand plays a crucial role in the C-H activation step of the oxidative Heck reaction. The presence of bipy-6-OH is required for the alkenylation of low acidity fluoroarenes, while it is detrimental for high acidity fluoroarenes. The use of catalytic amount of sodium molybdate as a base is optimal in all these reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Sif T. Linde, Vasco Corti, Vibeke H. Lauridsen, Johannes N. Lamhauge, Karl Anker Jorgensen, Nomaan M. Rezayee
Summary: This article presents a method for obtaining a versatile chiral biaryl structure through C-H halogenation reactions using high-valent Pd catalysis and chiral transient directing groups. The method is scalable, moisture and air insensitive, and in some cases, requires low Pd-loadings of only 1 mol%. Chiral mono-brominated, dibrominated, and bromochloro biaryls can be prepared in high yield and excellent stereoselectivity, serving as building blocks for various reactions with orthogonal synthetic handles.
Article
Chemistry, Organic
Yangyang Wang, Xiaobo Xu, Binghan Pang, Liqiang Hao, Gaorong Wu, Yafei Ji
Summary: In this study, the palladium-catalyzed sequential C(sp(3))-H and C(sp(2))-H bond diolefination reaction of o-toluidine was achieved using acetyl-protected aminoethyl phenyl thioether ligands. This novel reaction allows for the preparation of conjugated diene structure via an immediate second olefination, based on the first C(sp(3))-H olefination, in one pot. Various triflyl-protected anilines and acrylates were elegantly used as coupling partners. Furthermore, the unpurified diolefination products can be easily converted to tetrahydroquinoline derivatives.
Article
Chemistry, Physical
Hang Wang, Huiling Li, Xiahe Chen, Chunlin Zhou, Shangda Li, Yun-Fang Yang, Gang Li
Summary: In this study, a chiral ligand-controlled, asymmetric remote meta-C-H activation method was reported. By using a specific chiral ligand and Pd(II) catalyst, asymmetric C-H olefination and arylation of arenes were achieved. The origins of enantioselectivity were explained through density functional theory calculations.
Article
Chemistry, Multidisciplinary
Luo-Yan Liu, Zhoulong Fan, Md Emdadul Hoque, Shaoqun Qian, Guangrong Meng, Nikita Chekshin, Keita Tanaka, Jennifer X. X. Qiao, Kap-Sun Yeung, Jin-Quan Yu
Summary: Remote C-H functionalization of heterocyclic biaryls is crucial in synthesis and medicinal chemistry. New catalytic templates have been developed to functionalize the hindered ortho-C-H bonds of heterobiaryls, using directing heteroatom at the meta- or para-positions, with unprecedented site-selectivity. This protocol overcomes steric and electronic effects, allowing olefination of sterically hindered heterobiaryls.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Hang Wang, Huiling Li, Xiahe Chen, Chunlin Zhou, Shangda Li, Yun-Fang Yang, Gang Li
Summary: The use of a chiral ligand-controlled, asymmetric remote meta-C-H activation enables asymmetric C-H olefination and arylation of hydrocinnamic acid derivatives. The origins of the enantioselectivity were explained using density functional theory calculations.
Article
Chemistry, Physical
Guoshuai Li, Yifei Yan, Pengfei Zhang, Xiaohua Xu, Zhong Jin
Summary: A new palladium-catalyzed meta-selective C-H olefination of aromatic carbonyl compounds was achieved by utilizing noncovalent hydrogen-bonding interaction directed by engineered N,N'-substituted ureas, demonstrating site-selective control without the need for prior stoichiometric installation and removal of directing groups.
Article
Chemistry, Applied
Takahiro Yamada, Kosaku Tanaka, Yoshimitsu Hashimoto, Nobuyoshi Morita, Osamu Tamura
Summary: Here, the authors describe a reaction system based on Pd(II) catalyst and Tl(OCOCF3)3 for the electrophilic C3-H alkenylation of 2,6-dialkoxypyridines with alkenes. The synergistic action of the Pd/thioether ligand catalytic system and Tl(III) enables efficient C-H alkenylation of various nitrogen heteroaromatics with complete regioselectivity. Mechanistic studies suggest that the reaction proceeds via electrophilic thallation of heteroarenes followed by Pd-catalyzed Heck-type reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Dominik Lichte, Nico Pirkl, Gregor Heinrich, Sayan Dutta, Jonas F. Goebel, Debasis Koley, Lukas J. Goossen
Summary: This study demonstrates the achievement of para-C-H arylation of non-activated aryl halides with anilines using a base-assisted metalla-tautomerism approach. The challenge of directing functionalization towards the furthest C-H group has been overcome.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Md. Emdadul Hoque, Jin-Quan Yu
Summary: In this study, we report a new method for the gamma-arylation and gamma-lactonization of aliphatic acids, enabled by a L,X-type CarboxPyridone ligand catalyzed Pd(II) reaction. A wide range of gamma-arylated gamma-lactones can be efficiently synthesized in a single step, and the arylated lactones can be further converted into disubstituted tetrahydrofurans, which are prominent scaffolds in bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Mixiang Tian, Lidong Shao, Xiaosan Su, Xuhong Zhou, Honglei Zhang, Kun Wei, Ruifen Sun, Junliang Wang
Summary: A new method has been developed for selective oxygenation of benzaldehydes and benzylic amines at the ortho positions to prepare fluoroalkyl aryl ethers.
Article
Chemistry, Multidisciplinary
Anton Kudashev, Olivier Baudoin
Summary: A ligand-controlled site-selective C(sp(3))-H arylation of heteroaromatic ketones has been developed using Pd catalysis, with selective reactions occurring at the alpha- or beta-position of the ketone side-chain. Addition of a pyridone ligand enables switching from alpha- to beta-arylation. The alpha-arylation process demonstrates broad scope and high site- and chemoselectivity, while the beta-arylation is more limited, with mechanistic investigations suggesting different pathways for the two processes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Jyoti Dhankhar, Micha D. Hofer, Anthony Linden, Ilija Coric
Summary: This article presents a new selectivity mode for C-H arylation reactions, which is the preference for C(sp(2))-H activation next to alkyl groups. The study results indicate that this preference is related to the non-covalent interactions between the catalyst and the substrate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Verena Sukowski, Manuela van Borselen, Simon Mathew, M. Angeles Fernandez-Ibanez
Summary: By reversing conventional site-selectivity of C-H activation, a new catalytic system based on palladium/norbornene and an S,O-ligand for meta-C-H arylation of aryl ethers is reported, which outperforms previously reported systems. This system shows unique ability to use alkoxyarene substrates with different substituents, as well as tolerate ortho-substituted aryl ethers by employing novel norbornene mediators. Moreover, monoarylation of alkoxyarenes is achieved for the first time, enabling rapid introduction of a second, different aryl coupling partner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jia Zhou, Zi-Hao Li, Le Wang, Jun-Chen Kang, Xun-Hui Wang, Shu-Yu Zhang
Summary: This study introduces a highly efficient enantioselective para-C-H alkylation of aniline derivatives promoted by a base/Co/indeno-pybox ligand system, leading to the construction of enantioenriched compounds with all-carbon quaternary stereocenters. In addition, biologically or medicinally active indoles can be synthesized through Co-catalyzed asymmetry synthesis method. The role of the (acac)(-) anion of Co(acac)(2) in chiral control during the nucleophilic reaction is highlighted by density functional theory calculations and experimental results.
Article
Chemistry, Organic
Qiufeng Huang, Shurong Fu, Shaojia Ke, Hanbing Xiao, Xiaofeng Zhang, Shen Lin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Qiufeng Huang, Qingshuai Han, Shurong Fu, Zizhu Yao, Lv Su, Xiaofeng Zhang, Shen Lin, Shengchang Xiang
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Qingshuai Han, Shurong Fu, Xiaofeng Zhang, Shen Lin, Qiufeng Huang
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Organic
Xinyu Zhang, Lv Su, Lin Qiu, Zhenwei Fan, Xiaofeng Zhang, Shen Lin, Qiufeng Huang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Xiemin Guo, Qingshuai Han, Ziyuan Tang, Lv Su, Xinyu Zhang, Xiaofeng Zhang, Shen Lin, Qiufeng Huang
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Applied
Qingshuai Han, Xiemin Guo, Ziyuan Tang, Lv Su, Zizhu Yao, Xiaofeng Zhang, Shen Lin, Shengchang Xiang, Qiufeng Huang
ADVANCED SYNTHESIS & CATALYSIS
(2018)
Article
Chemistry, Physical
Qiufeng Huang, Shaojia Ke, Lin Qiu, Xiaofeng Zhang, Shen Lin
Article
Chemistry, Organic
Guoshuai Pan, Kongchuan Wu, Zeying Deng, Xinyu Zhang, Xiaofeng Zhang, Shen Lin, Qiufeng Huang
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Anyi Liu, Qingshuai Han, Xiaofeng Zhang, Buhong Li, Qiufeng Huang
Article
Chemistry, Organic
Yumeng Yuan, Guoshuai Pan, Xiaofeng Zhang, Buhong Li, Shengchang Xiang, Qufeng Huang
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Weihui Zhuang, Jiaqi Zhang, Yanping Zheng, Qiufeng Huang
Summary: This study accomplished the synthesis of valuable indole compounds through rhodium-catalyzed oxidative annulation, using atmospheric air pressure as the sole oxidant and facilitated by quaternary ammonium salt. Mechanistic studies revealed the fast intramolecular aza-Michael reaction and aerobic reoxidation of Rh(I)/Rh(III) enabled by the addition of quaternary ammonium salt.
Article
Chemistry, Organic
Piao Lu, Weihui Zhuang, Leipeng Lu, Anyi Liu, Yixi Chen, Chenmeng Wu, Xiaofeng Zhang, Qiufeng Huang
Summary: Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials has been achieved. Mn(OAc)3.2H2O selectively promotes different reactions leading to the formation of two distinct products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yumeng Yuan, Guoshuai Pan, Xiaofeng Zhang, Qiufeng Huang
ORGANIC CHEMISTRY FRONTIERS
(2020)
Article
Chemistry, Organic
Lu Su, Hanbing Xiao, Yumeng Yuan, Xiaofeng Zhang, Shen Lin, Qiufeng Huang
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2017)
