Article
Chemistry, Organic
Lukas V. Hoff, Joana M. Hauser, Karl Gademann
Summary: An efficient method utilizing Pd catalysis for cross-coupling of 5-bromo-1,2,3-triazine is described. Optimization of reaction conditions enables the preparation of a diverse range of (hetero)aryl-1,2,3-triazines in high yields (up to 97%). Assessment of the reaction scope using data science techniques and subsequent diversification of products allows for the efficient synthesis of pyrimidines and pyridines.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bryan C. Figula, D. Lucas Kane, Kaluvu Balaraman, Christian Wolf
Summary: Cross-coupling of alkyl fluorides and organocuprates is achieved via aluminum halide mediated C-F bond activation, leading to the formation of Csp2-Csp3 and Csp3-Csp3 bonds. The reaction exhibits mild conditions and effectively controls competing side reactions, resulting in high yields and good functional group tolerance.
Review
Chemistry, Organic
Matiur Rahman, Sumit Ghosh, Dhananjay Bhattacherjee, Grigory Zyryanov, Avik Kumar Bagdi, Alakananda Hajra
Summary: The carbon-carbon and carbon-heteroatom bond forming coupling reactions are fundamental in organic chemistry and widely used in the synthesis of valuable compounds. Microwave-assisted organic synthesis (MAOS) is an emerging technology that offers convenient and eco-friendly methods for designing target molecules.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Gyumin Kang, Sunkyu Han
Summary: In this study, we successfully synthesized dimeric high-oxidation-state securinega alkaloid Flueggeacosine B via two synthetic routes. The second-generation synthesis was more streamlined and a new reaction was developed to provide a direct pathway for the synthesis of compounds with a conjugated dicarbonyl moiety.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
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)
Review
Chemistry, Physical
Kuai Wang, Wangqing Kong
Summary: Organofluorine compounds have received significant attention in various industries due to their unique chemical and physical properties. However, the synthesis of these compounds still faces challenges, including difficulties in handling fluorinating reagents and controlling chemoselectivity. In recent decades, the development of Nickel-catalyzed defluorinative cross-couplings has provided powerful strategies for the construction of fluorinated organic compounds. This review summarizes important advances in this field, focusing on aryl fluorides, gem-difluorovinyl, and trifluoromethyl compounds.
Review
Chemistry, Physical
Younis Baqi
Summary: One of the most challenging tasks in organic synthesis is to achieve cross-coupling reactions furnishing carbon-carbon and carbon-heteroatom bonds using copper catalysis. In recent years, the use of microwave-assisted copper catalyzed cross-coupling reactions has significantly improved reaction efficiency and yield.
Article
Chemistry, Multidisciplinary
Muhammad Syafiq Bin Shahari, Edward R. T. Tiekink, Anton V. Dolzhenko
Summary: A new method for the synthesis of bis(1,3,5-triazine-2,4-diamines) has been developed using a one-pot multicomponent approach. The method involves the acid-catalyzed reaction of cyanoguanidine with amines and aldehydes, followed by dehydrogenative aromatization of the dihydrotriazine intermediates upon heating with alkali. The microwave-assisted method allows fast and convenient synthesis of diverse bis(1,3,5-triazine-2,4-diamines).
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)
Article
Chemistry, Organic
Bincy Chindan, Anagha Syam, Hariharan Mahendran, Ramesh Rasappan
Summary: In this study, a method for synthesizing α-vinyltrialkoxysilanes via cross-electrophile C(sp(2))-C(sp(2)) coupling was reported. The method demonstrates high compatibility with functional groups under milder reaction conditions.
Review
Chemistry, Organic
Carolina G. S. Lima, Fernanda P. Pauli, Vinicius G. Madriaga, Adriane A. P. Amaral, Isabela A. Graciano, Vinicius L. Meira, Luana da S. M. Forezi, Vitor F. Ferreira, Thiago de M. Lima, Fernando de Carvalho da Silva
Summary: Reactions promoting carbon-carbon bond formation are crucial in organic synthesis, and cross-coupling reactions are commonly used for this purpose. Supramolecular chemistry has emerged as a significant player in this field, offering approaches such as complex structure synthesis, scaffold modification, and repurposing of available materials like agarose. This Review primarily focuses on the development of supramolecular catalysts for Suzuki, Heck, and Sonogashira reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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)
Article
Nanoscience & Nanotechnology
Xuewen Guo, Jabor Rabeah, Ruixue Sun, Dengxu Wang, Esteban Mejia
Summary: A series of hybrid porous polymers (HPPs) based on polyhedral oligomeric silsesquioxane (POSS) were synthesized and successfully used as metal-free heterogeneous photocatalysts for cross-dehydrogenative coupling reactions, showing efficient catalytic performance under visible light. The novel catalysts can be easily recovered and reused, with mechanistic investigations revealing the oxidation-reduction process during photoexcitation.
ACS APPLIED MATERIALS & INTERFACES
(2021)
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
Oncology
P. Dao, N. Smith, D. Scott-Algara, C. Garbay, J. P. Herbeuval, H. Chen
Article
Chemistry, Medicinal
Pascal Dao, Rafika Jarray, Johanne Le Coq, Daniel Lietha, Ali Loukaci, Yves Lepelletier, Reda Hadj-Slimane, Christiane Garbay, Francoise Raynaud, Huixiong Chen
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2013)
Article
Oncology
Pascal Dao, Rafika Jarray, Nikaia Smith, Yves Lepelletier, Johanne Le Coq, Daniel Lietha, Reda Hadj-Slimane, Jean-Philippe Herbeuval, Christiane Garbay, Francoise Raynaud, Huixiong Chen
Article
Chemistry, Medicinal
Pascal Dao, Nikaia Smith, Celine Tornkiewicz-Raulet, Expedite Yen-Pon, Marta Carnacho-Artacho, Daniel Lietha, Jean-Phillipe Herbeuval, Xavier Commoul, Christiane Garbay, Huixiong Chen
JOURNAL OF MEDICINAL CHEMISTRY
(2015)
Article
Chemistry, Organic
Pascal Dao, Christiane Garbay, Huixiong Chen
Article
Chemistry, Organic
Huixiong Chen, Pascal Dao, Alice Laporte, Christiane Garbay
TETRAHEDRON LETTERS
(2010)
Article
Chemistry, Physical
Mauro Safir Filho, Pascal Dao, Anthony R. Martin, Rachid Benhida
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Pascal Dao, Daniel Lietha, Melanie Etheve-Quelquejeu, Christiane Garbay, Huixiong Chen
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Biochemistry & Molecular Biology
Pascal Dao, Fefei Ye, Yan Liu, Zhi Yun Du, Kun Zhang, Chang Zhi Dong, Bernard Meunier, Huixiong Chen
ACS CHEMICAL NEUROSCIENCE
(2017)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
