By employing CuOAc as the catalyst, we realize a four-component reaction of 1,3-enynes, diselenides, DABCO·(SO), and cycloketone oxime esters, providing facile access to diverse cyanoalkylsulfonylated allenyl selenides in moderate to good yields. This reaction features high functional group tolerance and a broad substrate scope, enabling the regioselective, sequential formation of C-SO and C-Se bonds under mild reaction conditions. Moreover, the utility of this methodology is further illustrated through the late-stage functionalization of drug-based molecules.
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http://dx.doi.org/10.1021/acs.orglett.1c02665 | DOI Listing |
J Org Chem
December 2024
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Gaohai Road, Guiyang 550014, P. R. China.
A copper-catalyzed regioselective annulation reaction, conducted without ligands or oxidants, has been developed for the preparation of multisubstituted furans from the readily available starting materials, β-keto esters and propargyl acetates. This process accommodates a wide range of functional groups, resulting in furan skeletons with diverse substitution patterns. The method's potential synthetic utility is highlighted by its applicability in gram-scale preparations and late-stage modifications of natural products.
View Article and Find Full Text PDFJ Org Chem
December 2024
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, P. R. China.
An effective and economical copper-catalyzed approach for the synthesis of phosphorylated 1-isochromenes is reported. This method is the first example of focus on ketone phosphonylation to establish a C-P bond and 6-- cyclization to construct a C-O bond between aryl- and alkyl-substituted alkynylketones and H-phosphinate esters, H-phosphites, and H-phosphine oxides, resulting in chemo- and regioselective phosphorylated 1-isochromenes with moderate to excellent yields under smooth reaction conditions.
View Article and Find Full Text PDFOrg Lett
December 2024
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024, China.
A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation of 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl radical from sulfoxonium ylides adds to the carbon-carbon double bonds of styrenes or 1,3-enynes, and the generated benzylic or allenyl radicals couple with a Cu(II) cyanide complex to achieve selective cyanation. The reaction exhibits high chemo- and regioselectivity and a wide substrate scope, providing an efficient method for the synthesis of alkyl nitriles and allenyl nitriles in a single step.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea.
The synthesis of chiral 1,1-diaryl compounds, particularly those containing a pyridine moiety, is of significant interest due to their pharmaceutical applications. Here, we report the development of a copper-catalyzed enantioselective 1,4-hydropyridylation of conjugated dienes. Utilizing 2-fluoropyridine as the electrophile, CuOAc, and the chiral ligand Tol-BINAP, we optimized reaction conditions to achieve the desired chiral 1,1-diaryl products containing both a pyridine and a cis-crotyl group.
View Article and Find Full Text PDFChem Asian J
November 2024
Department of Chemistry, Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.
Despite the significant development and extensive application of phthalocyanine and related azaporphyrins, little attention has been paid to meso-N-substituted azaporphyrinoids. Here, we report new derivatives of 5,10,20-triaryl-5,15-diazaporphyrinoids (ArDAP), which are reversibly redox-switchable between the 18π- and 19π-electron state. Four kinds of metal(II) complexes and free bases of ArDAP were prepared by metal-templated cyclization of metal(II) complexes of 5,10,15-triaryl-10-azabiladiene-ac with sodium azide or copper-catalyzed N-phenylation of 10,20-diaryl-5,15-diazaporphyrins (ArDAP) with diphenyliodonium hexafluorophosphate.
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