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Intermediate Control: Unlocking Hitherto Unknown Reactivity and Selectivity in N-Conjugated Allenes and Alkynes.
Acc Chem Res
January 2025
Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.
View Article and Find Full Text PDFSynthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[]fluoranthenes via a Pd-catalyzed Suzuki-Miyaura/C-H arylation cascade.
Beilstein J Org Chem
December 2024
Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye.
Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45-90%). This cascade involves an initial Suzuki-Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C-H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[]fluoranthenes, which are all structurally relevant to benzo[]fluoranthene-based fungal natural products.
View Article and Find Full Text PDFPhotocatalytic Oxidative Coupling of Benzyl Alcohol and Benzylamine for Imine Synthesis Using Immobilized CsBiBr Perovskite.
Small
December 2024
LSRE-LCM - Laboratory of Separation and Reaction Engineering - Laboratory of Catalysis and Materials, Faculty of Engineering, University of Porto, Rua Dr Roberto Frias, Porto, 4200-465, Portugal.
The oxidative cross-coupling of benzyl alcohol (BA) and benzylamine (BZA) is employed for the production of the corresponding imine, N-benzylidenebenzylamine (BZI), under visible light irradiation (light-emitting diodes (LE with λ = 417 nm) and mild reaction conditions. The cesium bismuth halide perovskites (CsBiBr, CBB) are synthesized by a one-step solution process as a sustainable alternative for the widely used Pb-halide perovskites. The CBB photocatalyst is immobilized on a polyethylene terephthalate (PET) structure designed explicitly for three-dimensional (3D) printing to operate in both batch and continuous modes to overcome the need for a final catalyst separation step.
View Article and Find Full Text PDFPredesign of Covalent-Organic Frameworks for Efficient Photocatalytic Dehydrogenative Cross-Coupling Reaction.
Adv Mater
December 2024
National and Local Joint Engineering Research Center of MPTES in High Energy and Safety LIBs, Engineering Research Center of MTEES (Ministry of Education), and Key Lab. of ETESPG (GHEI), School of Chemistry, South China Normal University, Guangzhou, 510006, China.
The dehydrogenative cross-coupling reaction is the premier route for synthesizing important 4-quinazolinone drugs. However, it usually requires high reaction temperature and long reaction time, and the yield of the final product is low. Here two stable and photosensitive covalent-organic frameworks (COFs), TAPP-An and TAPP-Cu-An are purposefully designed and constructed to serve as unprecedented heterogeneous tandem catalysts to complete dehydrogenative cross-coupling reactions in a short time and under mild reaction conditions (room temperature and light), leading to the high-efficient photosynthesis of 4-quinazolinones.
View Article and Find Full Text PDFModular Synthesis of New Metalloid-Substituted Olefins from Diboryl(Silyl)Ethenes via Suzuki-Miyaura Reactions.
Int J Mol Sci
November 2024
Center for Advanced Technologies, Adam Mickiewicz University, Uniwersytetu Poznanskiego 10, 61-614 Poznan, Poland.
A novel approach towards synthesizing new metalloid-substituted olefins has been accomplished by transforming ()-1,2-diboryl-1-silylethenes through two consecutive Suzuki-Miyaura coupling reactions. This methodology provides an effective and selective way to obtain new, structurally different products, such as ()-1-silyl-1-boryl-2-arylethens, (1)-1-silyl-1-boryl-2-alkenylethens, and ()-1-silyl-1-aryl-2-arylethenes, which are difficult to synthesize through hydrometallation reactions and related processes. Due to the presence of reactive motifs (silyl group, Bpin moiety, and C-H bond) in the structure of the final products, these molecules might be considered powerful building blocks in modern chemistry.
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