The nitrosonium ion-catalyzed dehydrogenative coupling of heteroarenes under mild reaction conditions is reported. The developed method utilizes ambient molecular oxygen as a terminal oxidant, and only water is produced as byproduct. Dehydrogenative coupling of heteroarenes translated into the rapid discovery of novel hedgehog signaling pathway inhibitors, emphasizing the importance of the developed methodology.
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http://dx.doi.org/10.1021/acs.orglett.8b00521 | DOI Listing |
Org Biomol Chem
January 2025
Key Laboratory of Green Chemical Process of Ministry of Education, Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan 430073, P.R. China.
Electrochemical oxidative cross-dehydrogenative-coupling (CDC) is an ideal strategy to conduct the C3-alkoxylation of imidazo[1,2-]pyridine, but it remains a challenge owing to limitation imposed by the use of alkyl alcohols and carboxylic acids. Herein, we report a mild and efficient 2-electrode constant-potential electrolysis of imidazo[1,2-]pyridine with hexafluoroisopropanol (HFIP) to produce various imidazo[1,2-]pyridine HFIP ethers. Mechanistic studies indicated that the electrooxidation reaction might involve radical coupling and ionic reaction.
View Article and Find Full Text PDFSmall
January 2025
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331, China.
In the chemical vapor deposition (CVD) synthesis of graphene, the surficial chemical state of the metal substrate has exerted key roles in all elemental reaction steps determining the growth mechanism of graphene. Herein, a CO-participated annealing procedure is designed to construct catalytic CuO/Cu sites on Cu foil for the graphene CVD synthesis with CO/CH as carbon sources. These CuO/Cu species can catalyze the CH decomposition and subsequent C─C coupling to form C intermediates for fast growth of monolayer hexagonal graphene domains with a diameter of ≈30 µm within 0.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu & Kashmir, 180001, India.
Herein, we disclose the development of novel aminomethylation and dicarbonylation reactions of imidazo[1,5-]pyridines. The developed aminomethylation strategy involves a Pd-catalyzed interrupted borrowing hydrogen strategy by utilizing MeOH as the methylene source. A wide variety of imidazo[1,5-]pyridines and secondary amines were explored for the developed strategy.
View Article and Find Full Text PDFMolecules
January 2025
Department of Chemistry, Fudan University, Shanghai 200438, China.
This review highlights significant advances in iron-catalyzed cross-dehydrogenative coupling (CDC), a method pivotal for forming carbon-carbon (C-C) bonds directly from C-H bonds. This technique uses iron-a naturally abundant, inexpensive, and environmentally benign transition metal-as a catalyst to facilitate the coupling of two unfunctionalized C-H bonds. This method stands out for avoiding pre-functionalized substrates, reducing both waste and cost in organic synthesis.
View Article and Find Full Text PDFNat Commun
January 2025
University of St Andrews, School of Biology, North Haugh, Biomolecular Sciences Building, St Andrews, UK.
Cyclic dipeptides are produced by organisms across all domains of life, with many exhibiting anticancer and antimicrobial properties. Oxidations are often key to their biological activities, particularly C-C bond oxidation catalysed by tailoring enzymes including cyclodipeptide oxidases. These flavin-dependent enzymes are underexplored due to their intricate three-dimensional arrangement involving multiple copies of two distinct small subunits, and mechanistic details underlying substrate selection and catalysis are lacking.
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