Article
Chemistry, Physical
Sanita B. Tailor, Mattia Manzotti, Gavin J. Smith, Sean A. Davis, Robin B. Bedford
Summary: The cobalt-catalyzed Suzuki biaryl cross-coupling reaction using alkoxide bases, with strict stoichiometric control and selection of the right boron ester, is shown to be achievable. Excessive alkoxide bases or lithium additives can inhibit or poison the catalyst, while a neopentane diol-based boron ester is crucial for optimal performance.Mechanistic and computational studies have been carried out to investigate the reaction mechanism and explain unexpected observations.
Article
Chemistry, Multidisciplinary
Shuo Yang, Guang Chen, Qing-Hao Xu, Bin Xiao
Summary: A simple method for the synthesis of cyclopropane compounds through the cross-coupling reaction between tertiary cyclopropyl carbagermatranes and acyl chlorides was reported. Derivatives of acryloyl chloride and aliphatic acyl chloride were also found to be suitable substrates. This method allows for the direct introduction of a wide range of functionalized cyclopropane and acyl groups.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Sheng Zhang, Junchao Yin, Ziyang Wang, Yang Li, Yukang Fu, Ji Ma, Zhilong Xie, Ming Bao
Summary: A palladium-catalysed aromative benzylic allylation and allenylation of benzyl chlorides with allyl and allenyl pinacolborates is reported for the first time. The reactions are conducted smoothly in the presence of a bidentate phosphine ligand, yielding good cross-coupling products. This new synthetic method exhibits excellent tolerance for various functional groups and is compatible with sensitive groups such as NO2, CF3, CN, and COOMe. The utilization of a bidentate ligand and heating is crucial for the transformation. DFT calculation results reveal the importance of wide-bite-angle bidentate ligands for the formation of an eta(1)-benzyl-eta(1)-allylpalladium intermediate and the thermodynamic favorability of the normal coupling reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Chuntao Zhong, Huiling Tang, Benqiang Cui, Yanhui Shi, Changsheng Cao
Summary: This article describes a palladium-catalyzed Suzuki cross-coupling reaction of benzyl ammonium triflates via activation of a Csp(3)-N bond to construct a Csp(3)-Csp(2) bond. The reaction exhibits a wide substrate scope and functional group tolerance, and can be successfully performed in a one-pot process.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Organic
Qianqian Lu, Haixing Guan, Yan-En Wang, Dan Xiong, Tingzhi Lin, Fei Xue, Jianyou Mao
Summary: A visible-light-promoted nickel/photoredox-catalyzed reductive cross-coupling reaction between vinyl bromides and benzyl chlorides has been reported, enabling the synthesis of a diverse array of enantioenriched allylic centers in good yields and high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ruoqian Fan, Meiying Kuai, Dong Lin, Felix Bauer, Weiwei Fang
Summary: A new palladacyclic N-heterocyclic carbene pre-catalyst was designed and successfully applied for Pd-catalyzed C-N cross-coupling reactions of challenging heteroaryl chlorides. The desired aminated products were achieved in good to excellent yields.
Article
Chemistry, Multidisciplinary
Raj Laxmi, Ravi Prakash Behere, Arunava Manna, Biplab Kumar Kuila
Summary: A reusable polymer-embedded Pd nanoparticle dip-catalyst membrane was developed to meet the criteria for a successful catalyst, including simple fabrication, high efficiency, stability, flexibility, straightforward recovery, reusability, and ease of scale-up. This membrane achieved high yields in various C-C bond formation reactions and moderate to good yields in C-X bond formations under mild reaction conditions. The system demonstrated stability, no significant leaching of Pd, and functional group tolerance.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tamae Seo, Koji Kubota, Hajime Ito
Summary: Mechanochemical synthesis using transition-metal catalysts has advantages such as low solvent waste and short reaction times. However, the direct use of transition-metal catalysts in mechanochemical reactions without modifications limits the development of efficient cross-coupling processes. This study presents a new approach, using mechanochemistry-directed design to develop ligands for Suzuki-Miyaura cross-coupling reactions. The embedding of the ligand into a poly(ethylene glycol) polymer prevents catalyst deactivation and shows high catalytic activity at room temperature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Ilja Rodstein, Leif Kelling, Julian Loffler, Thorsten Scherpf, Abir Sarbajna, Diego M. Andrada, Viktoria H. Gessner
Summary: The use of simple PdCl2 complexes stabilized through a unique bonding motif with ylide-substituted phosphines (YPhos) as efficient precatalysts has improved the efficiency of C-X cross-coupling reactions.
Article
Chemistry, Organic
Giorgio Rizzo, Gianluigi Albano, Teresa Sibillano, Cinzia Giannini, Roberta Musio, Fiorenzo G. Omenetto, Gianluca M. Farinola
Summary: This paper reports the application of a silk fibroin-supported Palladium catalyst (Pd/SF) in Suzuki-Miyaura and Ullmann coupling reactions of aryl chlorides. The existence of catalytic pockets where monoatomic palladium species can form stable complexes with SF is hypothesized and supported by experimental analysis. The size of the catalytic pocket of Pd/SF is estimated to be approximately 15 angstroms using computational modeling.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Charu Sharma, Avinash K. Srivastava, Deepak Sharma, Raj K. Joshi
Summary: This article presents a significantly upgraded Ullmann reaction for C-N cross couplings of aryl/alkyl chlorides. The method works in completely opposite conditions and is significantly influenced by various 3d transition metals, resulting in improved reaction time and catalytic activity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Shuo Yang, Wei-Tao Jiang, Bin Xiao
Summary: The study focused on tertiary cyclopropyl carbagermatranes obtained through zinc-mediated decarboxylation, which showed efficient reactivity in palladium-catalyzed cross-coupling reactions. They also exhibited orthogonal reactivity with boron reagents, acting as robust nucleophiles for the synthesis of tertiary cyclopropane and efficient intermediates for quaternary center formation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Sumanta Let, Gourab K. Dam, Partha Samanta, Sahel Fajal, Subhajit Dutta, Sujit K. Ghosh
Summary: By strategically integrating a homogeneously dispersed palladium coordinated N-heterocyclic carbene (NHC) inside a microporous hyper-cross-linked polymer, highly efficient and environmentally friendly catalytic reactions are achieved. The catalyst shows remarkable catalytic activity, functionality tolerance, and reusability.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Vignesh Palani, Melecio A. Perea, Richmond Sarpong
Summary: This review discusses strategies for site-selective functionalization of polyhalogenated arenes and heteroarenes, including traditional reaction types and emerging strategies.
Article
Chemistry, Organic
Nicholas E. Bode, Ryan T. McGuire, Mark Stradiotto
Summary: In this study, an effective catalyst system, PhPAd-DalPhos/NiCOD2, was identified and applied for the O-arylation of substituted phenols with chloropyridine-type electrophiles under thermal conditions, leading to pyridyl-O-aryl frameworks that are present in active pharmaceutical ingredients.
