Article
Chemistry, Physical
Sarah B. Pawley, Allyssa M. Conner, Humair M. Omer, Donald A. Watson
Summary: General conditions for the Hiyama-Denmark cross coupling of tetrasubstituted vinyl silanes and aryl halides are reported, enabling the coupling of unactivated vinyl silanes and displaying high stereospecificity. This important discovery simplifies the reaction procedure and reduces the use of toxic additives.
Article
Chemistry, Organic
Athmanand Anchi, Shruti S. S. Malunavar, Ravi S. S. Naik, Rajesh G. G. Kalkhambkar, Kenneth K. K. Laali
Summary: The application of conventional and ionic liquid solvents and reagents in the Hiyama cross-coupling reactions using triazenes as coupling partners was studied. Effective and respectable yields were obtained within minutes using microwave-assisted and Pd-catalyzed reactions in various solvents. The IL reagents and solvents were also successfully used to develop stepwise and sequential/tandem Hiyama-Suzuki (H S) and Hiyama-Heck (H H) methods.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Materials Science, Paper & Wood
Pouya Ghamari Kargar, Milad Nayebi, Zahra Parhizi, Rajender S. Varma
Summary: An eco-friendly approach was used to generate Ni nanoparticles on a magnetized cellulose biopolymer, resulting in a core-shell type nanocomposite (Fe3O4@CNF@Ni). The nanocomposite was characterized using various advanced techniques and its catalytic performance was evaluated in the synthesis of biaryl derivatives. The results showed that the nanocomposite exhibited high stability and catalytic efficiency.
Article
Chemistry, Multidisciplinary
Aurelien Adenot, Lucile Anthore-Dalion, Emmanuel Nicolas, Jean-Claude Berthet, Pierre Thuery, Thibault Cantat
Summary: A new air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction for the synthesis of diaryl sulfones has been developed, tolerating a wide range of polar functional groups. Control experiments and DFT calculations elucidated the mechanism involving the formation of a Cu(I)-sulfinate intermediate through fast insertion of a SO2 molecule.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Subrata Das, Andreas W. Ehlers, Sima Patra, Bas de Bruin, Buddhadeb Chattopadhyay
Summary: A concept for intermolecular C-N cross-coupling amination has been discovered using tetrazoles and aromatic and aliphatic azides with boronic acids under iron-catalyzed conditions. The reaction follows an unprecedented metalloradical activation mechanism, different from traditional metal-catalyzed C-N cross-coupling reactions. The wide scope of this reaction has been demonstrated by employing various tetrazoles, azides, and boronic acids. Moreover, the reaction has shown potential for applications in medicinal chemistry, drug discovery, and pharmaceutical industries, as demonstrated by late-stage aminations and synthesis of a drug candidate.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Vijaykumar H. Thorat, Hasil Aman, Yu-Lin Tsai, Gangaram Pallikonda, Gary Jing Chuang, Jen-Chieh Hsieh
Summary: This study explores the co-catalyzed reactions of 2-halobenzamides and alkynes to form isoquinolones or 2-vinyl benzamides, with the formation of selective products controlled by ligands. The mechanism study reveals that these reactions proceed through different pathways, involving radical processes and two-electron transfer activation of the C-X bond.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Myuto Kashihara, Yoshiaki Nakao
Summary: Cross-coupling reactions using nitroarenes as electrophiles have gained attention due to their ease of accessibility and potential advantages over haloarenes. Recent research has focused on developing new catalyst systems and reaction conditions to improve the efficiency and practicality of these reactions, with promising results in diversifying bond-forming reactions and reducing catalyst loading. Research in this field is expected to continue growing as the utility of nitroarenes in organic synthesis is reevaluated.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Review
Chemistry, Multidisciplinary
Yaowen Liu, Pengfei Li, Yanwei Wang, Youai Qiu
Summary: Electrochemistry employs electrons as an efficient and sustainable alternative to chemical oxidants or reductants, and has gained popularity for selective organic synthesis. The combination of electrochemistry with readily available electrophiles has emerged as a viable method for constructing challenging C-C and C-heteroatom bonds. This mini-review provides a systematic summary of the recent advances in electroreductive cross-electrophile coupling (eXEC) reactions, focusing on aryl and alkyl organic (pseudo)halides, as well as small molecules such as CO2, SO2, and D2O.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Biochemistry & Molecular Biology
Rida Noor, Ameer Fawad Zahoor, Muhammad Irfan, Syed Makhdoom Hussain, Sajjad Ahmad, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: Hiyama cross-coupling is a versatile reaction that enables the construction of carbon-carbon bonds in synthetic organic chemistry. By coupling organosilicons with organic halides using transition metal catalysts, good yields and high enantioselectivities can be achieved. In recent years, researchers have made significant progress in using the Hiyama coupling reaction for the synthesis of diversified natural products and pharmaceutical drugs.
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xin-Xing Wu, Hao Ye, Guomin Jiang, Lanping Hu
Summary: This study describes a palladium-catalyzed domino Heck cyclization/Hiyama coupling reaction where the sigma-alkylpalladium intermediate is trapped with arylsilanes. A wide range of aryl-tethered alkenes and arylsilanes are compatible with the reaction conditions, showing good yields and excellent functional group tolerance. This approach presents a more practical and sustainable alternative to the conventional domino Heck cyclization/Suzuki coupling reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ayan Jati, Kaushik Dey, Maryam Nurhuda, Matthew A. Addicoat, Rahul Banerjee, Biplab Maji
Summary: This study presents a dual metalation strategy using a COF TpBpy for C-N cross-coupling reactions. The strategy demonstrates controlled metalation, recyclability, and visible-light-mediated catalysis. Experimental and theoretical studies provide insights into the catalyst and reaction mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Applied
Leila Rahimi, Yagoub Mansoori, Ayat Nuri, Behzad Koohi-Zargar, Dolores Esquivel
Summary: The magnetic mesoporous silica composite was prepared by embedding magnetite nanoparticles between SBA-15 channels and complexing with Pd(II). The supported Pd(II) catalyst showed high activity in Heck and Hiyama reactions, with better results observed for aryl bromides and iodides, and exhibited noticeable stability and reusability.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
