Article
Chemistry, Applied
Ying Fu, Liang-Liang Guo, Xi Chen, Hao Chen, Jia-Jia Liu, Fang-Rong Li, Cai-Qin Xiao, Zhengyin Du
Summary: A Cu/Pd co-catalyzed Catellani-type ortho arylation reaction of iodoarenes with aryl diazonium salts has been developed. Aryl radicals that derived from aryl diazonium salts were regioselectively installed at ortho position of iodoarenes via palladium catalyzed C-H activation. Mechanistic studies showed that, in contrast to classical Pd0-PdII-PdIV-PdII-Pd0 catalytic cycle, this radical cascades performed via a Pd0-PdII-PdIII-PdI-Pd0 cycle.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Nanoscience & Nanotechnology
Mateusz Michal Tomczyk, Masafumi Minoshima, Kazuya Kikuchi, Agata Blacha-Grzechnik, Zbigniew Starosolski, Rohan Bhavane, Mariusz Zalewski, Nikodem Kuznik
Summary: The attachment of functional molecules to single-walled carbon nanotubes (SWCNTs) using aryl diazonium salt chemistry can enhance their near-infrared emission. In this study, sp(3) defects were created on (6,5) SWCNTs using aryl diazonium salt of fluorescein. The pH was found to affect the grafting process, with pH 5-6 being necessary for a successful reaction. The modified SWCNTs exhibited red-shifted NIR emission due to luminescent sp(3) defects, as well as visible fluorescence from attached fluorescein molecules.
Article
Chemistry, Multidisciplinary
Gentiana Hasani, Avni Berisha, Dardan Hetemi, Philippe Decorse, Jean Pinson, Fetah I. Podvorica
Summary: This study focuses on modifying the surface of cheap lignite powder with alkyl or mixed alkyl-aryl layers. By using specific aqueous acid solutions, the researchers successfully attached alkyl or aryl films to the lignite surface. The stability of the interface during the grafting reactions was confirmed through theoretical calculations. Additionally, steric hindrance of aryl diazonium salts did not prevent them from reacting with the coal surface by abstracting iodine or bromine atoms.
Article
Chemistry, Multidisciplinary
Shi-Jing Zhai, Dominique Cahard, Fa-Guang Zhang, Jun-An Ma
Summary: Three bench-stable difluoromethylene phosphonate hydrazones were synthesized in good yields from simple diethyl(difluoromethyl)phosphonate within two steps. The [3 + 2] cycloaddition reaction with aryl diazonium salts under metal-free conditions exhibited exclusive regioselectivity. This method provides practical access to a wide range of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates, including derivatives of amino acids and drug cores.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Abigail J. Shepard, Julia A. Townsend, Christopher Foley, Christopher Hulme, Michael T. Marty, John C. Jewett
Summary: In this study, a Suzuki coupling strategy compatible with the triazabutadiene scaffold was reported, expanding the synthetic scope of triazabutadienes. The triazabutadiene scaffold remained intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.
Article
Chemistry, Organic
Kartic Manna, Ranjan Jana
Summary: We describe a mild and highly selective palladium-catalyzed cross-electrophile coupling between aromatic diazonium salts and aryl iodides or diaryliodonium salts in a water-ethanol (2:1) medium. Mechanistic studies revealed the importance of ethanol in generating an active Pd(0) catalyst, and the counterion of the diazonium salt promotes the formation of a cationic Pd(II) species that facilitates subsequent oxidative addition to aryl iodides/diaryliodonium salts. The presence of silver(I) salt is crucial for maintaining the catalytic activity of palladium by removing iodide ions as precipitates.
Article
Chemistry, Organic
J. N. Abrams
Summary: An alternative mild method for synthesizing 1-aryl-3,3-dimethyl alkyl triazenes has been described, utilizing radical pathways initiated by homolysis of weak N-O bonds in diazo ether adducts. This method provides modest yields (ca. 20-40%) across a range of aryl diazonium salts. The use of DMF as both an electron donor and a source of dimethylamine radicals sets this approach apart from traditional methods.
Article
Chemistry, Multidisciplinary
Wei Sun, Luke Wilding-Steele, Richard C. D. Brown, David C. C. Harrowven
Summary: Benzyloxy iodobenzene ethers can undergo cyclisation to form benzo[c]chromenes under UVC irradiation without the need for reagents or catalysts. The reactions proceed through the generation of triplet aryl cations, 5-exo and 3-exo-cyclisations, and subsequent rearomatisation. This methodology is versatile, convenient, and applicable to various related ring systems.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Na-Na Ma, Jing-Ao Ren, Xiang Liu, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
Summary: The direct cross-couplings of aryl sulfonium salts with aryl halides using nickel as a reaction catalyst were successfully achieved. The reactions proceeded efficiently via C-S bond activation at ambient temperature, providing moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Peng Wang, Jacob Fortner, Hongbin Luo, Jacek Kaos, Xiaojian Wu, Haoran Qu, Fu Chen, Yue Li, YuHuang Wang
Summary: Water unexpectedly acts as a nucleophilic agent in the diazonium reaction with carbon nanotubes involving chlorosulfonic acid, providing -OH as the pairing group. Replacing water with other nucleophilic solvents allows the creation of organic color centers (OCCs) with entirely new pairing groups, enabling systematic control over defect pairs and the optical properties of resulting color centers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Italo A. Sanhueza, Felix J. R. Klauck, Erdem Senol, Sinead T. Keaveney, Theresa Sperger, Franziska Schoenebeck
Summary: The study found that aryl diazonium salts exhibit different reactivities in Suzuki and Stille cross-couplings in MeOH, challenging the currently accepted mechanism. Experimental evidence suggests that the observed solvent dichotomy is primarily due to the formation of unreactive Pd(II)-methoxy intermediates with arylstannanes, but highly reactive with arylboronic acids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Electrochemistry
Quentin Lenne, Vivien Andrieux, Gael Levanen, Jean-Francois Bergamini, Pauline Nicolas, Ludovic Paquin, Corinne Lagrost, Yann R. Leroux
Summary: This study reports the efficient electro-grafting of aryl diazonium salts on carbon surfaces using ethaline as a deep eutectic solvent, demonstrating potential applications. The effects of concentration, deposition time, and potential on electrode blocking behavior and deposited organic film thickness were investigated. Post-functionalization with redox active moieties was also demonstrated on the electro-grafted organic layer.
ELECTROCHIMICA ACTA
(2021)
Article
Chemistry, Medicinal
Claire C. Fanta, Kaitlyn J. Tlusty, Sarah E. Pauley, Amanda L. Johnson, Genevieve A. Benjamin, Taylor K. Yseth, Michaela M. Bunde, Paul T. Pierce, Shirley Wang, Peter F. Vitiello, Jared R. Mays
Summary: This study describes the preparation and evaluation of a library of 79 non-natural isothiocyanate analogues, leading to the discovery of key structure-activity relationships and potent antiproliferative isothiocyanates.
Article
Chemistry, Organic
Cooper A. Vincent, Alexia Ripak, Ludovic Troian-Gautier, Uttam K. Tambar
Summary: A photocatalytic method is presented for converting aryl diazonium salts to aryl sulfonyl fluorides, which have emerged as powerful tools for selective protein labelling in chemical biology. The diazonium substrates can be easily obtained from functionalized anilines in one step. The optimization of this mild synthesis method for sulfonyl fluorides, as well as the range of conversion with functionalized diazonium salts, is discussed along with photophysical measurements providing detailed information on the mechanism of the photochemical process. © 2023 Elsevier Ltd. All rights reserved.
Article
Chemistry, Multidisciplinary
Gwang-Noh Ahn, Brijesh M. Sharma, Santosh Lahore, Se-Jun Yim, Shinde Vidyacharan, Dong-Pyo Kim
Summary: This study demonstrates that using a metal-based flow parallel synthesizer can achieve multiplex synthesis and parameter screening in multiple microreactors simultaneously, enabling the execution of various reactions under different conditions, which provides new possibilities for synthesizing drugs and lead molecules.
COMMUNICATIONS CHEMISTRY
(2021)
