A practical method for regioselective hydroarylation of unactivated γ- or δ-vinyl alkylamines has been reported, enabling facile preparation of highly value-added ε- or ζ-aryl alkylamines. The protocol employs nickel catalysis, shows high functional group tolerance and can be used for modifying bio-related molecules.
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http://dx.doi.org/10.1039/d2cc04932e | DOI Listing |
J Org Chem
January 2025
School of Chemistry, IGCME, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
The ligand-free Lewis acid-mediated regioselective hydroamination and hydroarylation of styrenes have been successfully developed in the presence of isatins or heterocyclic aryl compounds such as benzothiophenes and benzofurans. The reactions tolerate a variety of functional groups and afford the corresponding products in moderate to good yields. Deuterium labeling experiments show that the functionalized hydrogen of styrenes was derived from the nitrogen-hydrogen of the substrates in the hydroamination.
View Article and Find Full Text PDFChem Sci
October 2024
Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Tammannstraße 2 37077 Göttingen Germany
Hydroarylation reactions have emerged as a valuable tool for the direct functionalization of C-H bonds with ideal atom economy. However, common catalytic variants for these transformations largely require harsh reaction conditions, which often translate into reduced selectivites. In contrast, we herein report on a photo-induced hydroarylation of unactivated olefins at room temperature employing a readily available ruthenium(ii) catalyst.
View Article and Find Full Text PDFChemSusChem
October 2024
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.
Transition metal-catalyzed cross-coupling reaction between organometallic reagents and electrophiles is a potent method for constructing C(sp)-C(sp) bonds. Given the characters of organometallic reagents, cross-reductive coupling is emerging as an alternative strategy. The resurgence of electrochemistry offers an ideal method for electrochemical reductive of cross-coupling electrophiles.
View Article and Find Full Text PDFJ Org Chem
November 2024
CICA, Centro Interdisciplinar de Química e Bioloxía and Departamento de Química, Universidade da Coruña, 15071 A Coruña, Spain.
Pyrroles, privileged structural motifs in drug and material science, have been synthesized by indium(III)-catalyzed intramolecular cyclization of homopropargyl azides. This methodology exhibits a broad substrate scope, providing substituted pyrroles and bispyrroles in good yields. Furthermore, an atom-economical sequential method for the synthesis of benzo[]indoles has been discovered from azido-diynes using InCl as catalyst.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
October 2024
Graduate School of Biomedical and Health Sciences, Hiroshima University.
We studied the reaction pathway of our reductive Heck hydroarylation using a palladium catalyst and a hydrosilane. A key question to verify the reaction mechanism was which active species, Ar-Pd-I or Si-Pd-H, first performs migratory insertion into the alkenes. Identifying this step is crucial to elucidate the reaction mechanism.
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