The synthesis of bis- and trisoxazoles via direct arylation is discussed. A variety of aryl groups can be installed at the 2-position of 5-aryl and 5-carboxy-substituted oxazoles under mild conditions using palladium catalysis on water. The direct arylation method can be extended to the synthesis of bis- and trisoxazoles if 2-triisopropylsilyl-4-iodooxazole is used as the electrophile in the arylation.
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http://dx.doi.org/10.1021/ol800869g | DOI Listing |
Molecules
January 2025
Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.
A pyridine-fused triazapentalene shows weak fluorescence in solution and is readily accessible via nitrene-mediated cyclization. In this study, a modified Cadogan reaction was used to synthesize . Palladium-catalyzed reactions have been used as post-functionalization methods.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of Houston, Houston, Texas 77204-5003, United States.
Monoanionic, bidentate-auxiliary-directed, cobalt-catalyzed C-H bond functionalization has become a very useful tool in organic synthesis. A comprehensive investigation into isolated organometallic intermediates and their reactivity within the catalytic cycle is lacking. We report here mechanistic studies of cobalt-catalyzed, aminoquinoline-directed C(sp)-H bond functionalization.
View Article and Find Full Text PDFOrg Lett
January 2025
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
The C2- or C3-selective direct C-H arylation of nonsubstituted 1-pyrrole with aryl chlorides/nonaflates was achieved using catalysts derived from palladium and appropriate phosphine ligands. The site selectivity of the arylation can be switched by changing the ligands, and the C3-selective arylation of nonsubstituted 1-pyrrole was realized for the first time. BuOLi played an important role in suppressing N-arylation and accelerating C2- or C3-arylation.
View Article and Find Full Text PDFMini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFCatal Sci Technol
December 2024
Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern Freiestrasse 3 3012 Bern Switzerland
Even though α-arylation of ketones is attractive for direct C-H functionalization of organic substrates, the method largely relies on phosphine-ligated palladium complexes. Only recently, efforts have focused on developing nitrogen-based ligands as a more sustainable alternative to phosphines, with pyridine-functionalized pyridinium amidate (pyr-PYA) ,'-bidentate ligands displaying good selectivity and activity. Here, we report on a second generation set of catalyst precursors that feature a 5-membered N-heterocycle instead of a pyridine as chelating unit of the PYA ligand to provide less steric congestion for the rate-limiting transmetalation of the enolate.
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