Ruthenium-catalyzed isoquinolone syntheses with ample scope were accomplished through carboxylate assistance in environmentally benign water as a reaction medium. The high chemoselectivity of the ruthenium(II) carboxylate complex also set the stage for the direct use of free hydroxamic acids for annulations of alkynes.
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http://dx.doi.org/10.1021/ol202861k | DOI Listing |
Chemistry
December 2024
Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province, School of Pharmacy, Southwest Medical University, Luzhou, 646000, China.
A powerful EnT photocatalyst 4CzMeBN has been developed and utilized in the synthesis of cis-fused azetidines via dearomative [2+2] cycloaddition under visible light. The photocatalyst 4CzMeBN is a donor-acceptor cyanoarene and features high triplet state energy and long lifetime of triplet state, which would be an alternative to widely used EnT photocatalyst Ir[dF(CF)ppy](dtbbpy)PF. The photochemical [2+2] cycloaddition provides a facile method to synthesize valuable dihydroisoquinolone-fused azetidines with high efficiency.
View Article and Find Full Text PDFOrg Biomol Chem
November 2024
Department of Chemistry, Indian Institute of Technology Patna, Bihta 801106, Bihar, India.
In this study, we present the first cobalt(III)-catalyzed direct synthesis of isoquinolones from readily available primary arylamides and internal alkynes through a controlled oxidative C-H/N-H annulation reaction. This innovative protocol eliminates the need for expensive transition metal salts and external auxiliaries, producing the desired mono-annulated product exclusively while accommodating a wide range of substrates. Preliminary mechanistic studies highlight the critical role of copper oxide in facilitating the transformation.
View Article and Find Full Text PDFOrg Lett
April 2024
HitGen Inc., Building 6, No. 8 Huigu first East Road, Tianfu International Bio-Town, Shuangliu District, Chengdu 610200, Sichuan P. R. China.
Isoquinolone is one of the most common heterocyclic core structures in countless natural products and many bioactive compounds. Here, a highly efficient approach to synthesize isoquinolone scaffolds on DNA via rhodium(III)-catalyzed C-H activation has been described. This chemistry transformation is robust and has shown good compatibility with DNA, which is suitable for DNA-encoded library synthesis.
View Article and Find Full Text PDFChem Commun (Camb)
April 2024
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, P. R. China.
A palladium catalysed construction of fluoroalkyl indoles and isoquinolones through aryl/monofluoroalkylation of allenamides has been developed. Monofluoromethyl-substituted heterocycles could be accessed under mild conditions with broad functional group tolerance. In addition, indole-oxindole bisheterocyclic scaffolds bearing a fluorine atom were successfully synthesized with 3-fluoro-oxindole as the nucleophile by applying this method.
View Article and Find Full Text PDFAcc Chem Res
January 2024
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany.
ConspectusTo improve the resource economy of molecular syntheses, researchers have developed strategies to directly activate otherwise inert C-H bonds, thus avoiding cumbersome and costly substrate prefunctionalizations. During the past two decades, remarkable progress in coordination chemistry has set the stage for developing increasingly viable metal catalysts for C-H activations. Despite remarkable advances, C-H activations are largely dominated by precious 4d and 5d transition metal catalysts based primarily on palladium, ruthenium, iridium, and rhodium, thus decreasing the inherent sustainable nature of the C-H activation approach.
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