Heavy-atom-modified chalcogen-fused triarylamine organic materials are becoming increasingly important in the photochemical sciences. In this context, the general and direct dehydrogenative C-H phenochalcogenazination of phenols with the heavier chalcogens selenium and tellurium is herein described. The latter dehydrogenative C-N bond-forming processes operate under simple reaction conditions with highly sustainable O serving as the terminal oxidant.
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http://dx.doi.org/10.1021/acs.orglett.1c00573 | DOI Listing |
RSC Adv
January 2025
State Key Laboratory of Solidification Processing, Center for Nano Energy Materials, School of Materials Science and Engineering, Northwestern Polytechnical University (NPU), Shaanxi Joint Laboratory of Graphene Xi'an 710072 China
The oxidative dehydrogenation of propane with CO (CO-ODP) is a green industrial process for producing propene. Cerium oxide-supported platinum-based (Pt/CeO) catalysts exhibit remarkable reactivity toward propane and CO due to the unique delicate balance of C-H and C[double bond, length as m-dash]O bond activation. However, the simultaneous activation and cleavage of C-H, C-C, and C-O bonds on Pt/CeO-based catalysts may substantially impede the selective activation of C-H bonds during the CO-ODP process.
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 PDFAcc Chem Res
January 2025
Shenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China.
ConspectusChiral organosilicon compounds bearing a Si-stereogenic center have attracted increasing attention in various scientific communities and appear to be a topic of high current relevance in modern organic chemistry, given their versatile utility as chiral building blocks, chiral reagents, chiral auxiliaries, and chiral catalysts. Historically, access to these non-natural Si-stereogenic silanes mainly relies on resolution, whereas their asymmetric synthetic methods dramatically lagged compared to their carbon counterparts. Over the past two decades, transition-metal-catalyzed desymmetrization of prochiral organosilanes has emerged as an effective tool for the synthesis of enantioenriched Si-stereogenic silanes.
View Article and Find Full Text PDFChem Sci
January 2025
Aix Marseille University, Université de Toulon, CNRS, IM2NP 13013 Marseille France
We investigated the reactivity of a -dichlorovinyl-carbazole precursor in the on-surface synthesis approach. Our findings reveal that, on the Au(111) surface, the thermally-induced dehalogenation reaction led to the formation of cumulene dimers. Contrastingly, the more reactive Cu(111) surface promoted the formation of a polyheterocyclic compound exhibiting extended aromaticity.
View Article and Find Full Text PDFJ Org Chem
January 2025
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.
We herein disclose a visible-light-induced synthesis of aryl esters through the cross-dehydrogenative coupling of aldehydes with phenols using BrCCl, in which phenolate functions as both a substrate and a photosensitizer. This transition-metal- and photocatalyst-free visible-light-induced esterification is suitable for a wide range of substrates and gives moderate to excellent yields (up to 95%). Mechanistic studies provided evidence of a self-propagating radical reaction involving homolytic cleavage of the aldehydic C-H bond and the formation of acyl bromides.
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