We have developed cycloisomerization between an aryl vinyl ether and a functionalized alkyne, such as silylalkyne, to give 2,3-disubstituted benzofuran derivatives using [IrCl(cod)], PCy, and NaBAr. This catalyst system not only catalyzes the above cycloisomerization but also isomerize a terminal olefin to give an aryl vinyl ether.
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http://dx.doi.org/10.1021/acs.joc.0c00954 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Sichuan University, State Key Laboratory of Biotherapy, CHINA.
Herein we report a cobalt-catalyzed hydroglycosylation of terminal alkynes, employing bench-stable ortho-iodobiphenyl (oIB) substituted sulfides as glycosyl donors. This reaction occurs with high stereo- and regioselectivity to afford E-configured vinyl α-C-glycosides, a class of compounds nontrivial to access by previous methods. The use of a bis(oxazoline) ligand with bulky side chains is critical for the high selectivities observed.
View Article and Find Full Text PDFOrg Chem Front
December 2024
Department of Chemistry, University of Pittsburgh Pittsburgh Pennsylvania 15260 USA
Org Lett
January 2025
Key Laboratory of Chemical Biology of Fujian Province and State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Transition-metal-catalyzed [2 + 2 + 2] annulation of alkynes is an efficient pathway for the synthesis of aromatic compounds. However, most of the established methods require noble metal catalysts. Herein, we report a copper-catalyzed intermolecular [2 + 2 + 2] annulation of diynes with alkynes through vinyl cation intermediates, enabling the atom-economical preparation of biologically important carbazole skeletons.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.
Herein, we report a Ni-catalyzed cross-electrophile coupling of aryl/vinyl halides with benzothiazolium salts derived from alcohols. Our findings demonstrate that primary alkyl benzothiazolium salts serve as effective C(sp)-O substrates, facilitating coupling with aryl and vinyl halides. This method not only enables the formal functionalization of primary alcohols but also provides experimental support for previously established sequential alcohol halogenation and Ni-catalyzed reductive coupling platforms.
View Article and Find Full Text PDFJ Org Chem
January 2025
Institute of Materia Medica, School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816, P. R. China.
In this study, we present a novel catalyst-free energy transfer mediated radical rearrangement strategy for the aryl-heterofunctionalization of unactivated alkynes, leading to the synthesis of polyfunctional olefins with exceptional stereoselectivity. This innovative approach, driven by visible light, exemplifies green chemistry principles by eliminating the reliance on transition metals, external oxidants, and photocatalysts. The broad applicability of our method is demonstrated through the successful synthesis of a diverse array of compounds, including vinyl sulfones, vinyl selenides, and vinyl sulfides.
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