Herein we describe an alternative and unconventional approach of an aminocarbonylation reaction to access aryl amides from readily available and low-cost arylboronic acids and nitroarenes. Nickel metal can serve as both reductant and catalyst in this direct aminocarbonylation. This protocol exhibits a good functional group compatibility and allows a variety of aryl amides to be synthesized, including several drug-like molecules.
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http://dx.doi.org/10.1039/c9cc06638a | DOI Listing |
Beilstein J Org Chem
January 2025
Sagami Chemical Research Institute, 2743-1 Hayakawa, Ayase, Kanagawa 252-1193, Japan.
2-Fluorobenzofurans underwent efficient nickel-catalyzed coupling with arylboronic acids through the activation of aromatic C-F bonds. This method allowed us to successfully synthesize a range of 2-arylbenzofurans with various substituents. The reaction, which proceeded under mild conditions, involved β-fluorine elimination from nickelacyclopropanes formed by the interaction of 2-fluorobenzofurans with zero-valent nickel species.
View Article and Find Full Text PDFChemSusChem
January 2025
Comenius University FNS: Univerzita Komenskeho v Bratislave Prirodovedecka fakulta, Organic chemistry, Mlynska dolina, Ilkovicova 6, 84215, Bratislava, SLOVAKIA.
Cross-coupling reactions are indispensable for the construction of complex molecular scaffolds. In this work, we developed a sustainable methodology for the cross-coupling reaction of arene thianthrenium salts with aryl boronic acids, which can be effectively realized under mechanochemical conditions. Liquid-assisted grinding (LAG) enabled fast and high-yielding synthesis of a range of biaryls via Pd/RuPhos-catalyzed cross-coupling.
View Article and Find Full Text PDFComb Chem High Throughput Screen
January 2025
APIGENEX s.r.o., Poděbradská 173/5, Prague 19000, Czech Republic.
Objective: In search of efficient anticancer agents, we aimed at the design and synthesis of a library of tetrasubstituted alkenes. These are structural analogues of tamoxifen, one of the widely used anticancer therapeutics.
Methods: Our small organic compound library was prepared via a chemical synthesis in the solution using the Larock three-component coupling reaction, which is known to tolerate diverse functional groups.
Angew Chem Int Ed Engl
January 2025
New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Rhodium-catalyzed regio- and enantioselective allylic arylation of racemic alkyl- and aryl- substituted allylic carbonates with arylboronic acids using commercially available BIBOP ligand is reported. This reaction proceeds at room temperature without base or other additive to deliver allylic arylation products in excellent yields, regio- and enantioselectivity (up to 95 % yield, >20 : 1 b/l, >99 % ee). Rh/BIBOP is disclosed as an efficient catalytic system for allylic substitution reaction.
View Article and Find Full Text PDFJ Org Chem
January 2025
State Key Laboratory of Macromolecular Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, P. R. China.
The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety of poly substituted pyridines. The protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by tandem cyclization of enaminone intermediates with β-ketonitriles or enolates, respectively, and does not require extra ammonias. This method boasts notable advantages, such as the use of commercially available or easily prepared substrates, simple conditions, a broad substrate scope, and good functional group tolerance.
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