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Keywords = palladium-catalyzed alkoxycarbonylations

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11 pages, 2870 KiB  
Article
Palladium-Catalyzed Selective Carbonylation Reactions of Ortho-Phenylene Dihalides with Bifunctional N,O-Nucleophiles
by Fanni Bede, Attila Takács, László Kollár and Péter Pongrácz
Molecules 2024, 29(23), 5620; https://doi.org/10.3390/molecules29235620 - 27 Nov 2024
Viewed by 1303
Abstract
Palladium-catalyzed carbonylation reactions of ortho-phenylene dihalides were studied using aminoethanols as heterobifunctional N,O-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be [...] Read more.
Palladium-catalyzed carbonylation reactions of ortho-phenylene dihalides were studied using aminoethanols as heterobifunctional N,O-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production. Intramolecular double carbonylation reaction can be achieved using 1,2-diiodobenzene and amino alcohols featuring secondary amine groups, giving oxazocine derivatives. Useful reaction scope with various amino alcohols was performed with good isolated yields of the targeted compounds. Intramolecular C-O coupling of amide alcohols possessing bromo substituent in adjacent ortho position is also demonstrated as a potential next step in benzoxazepine heterocycle formation. Full article
(This article belongs to the Special Issue Advances in Transition-Metal-Catalyzed Synthesis)
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40 pages, 6368 KiB  
Review
Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product
by Haruhiko Fuwa
Mar. Drugs 2016, 14(4), 65; https://doi.org/10.3390/md14040065 - 25 Mar 2016
Cited by 50 | Viewed by 12226
Abstract
Tetrahydropyrans are structural motifs that are abundantly present in a range of biologically important marine natural products. As such, significant efforts have been paid to the development of efficient and versatile methods for the synthesis of tetrahydropyran derivatives. Neopeltolide, a potent antiproliferative marine [...] Read more.
Tetrahydropyrans are structural motifs that are abundantly present in a range of biologically important marine natural products. As such, significant efforts have been paid to the development of efficient and versatile methods for the synthesis of tetrahydropyran derivatives. Neopeltolide, a potent antiproliferative marine natural product, has been an attractive target compound for synthetic chemists because of its complex structure comprised of a 14-membered macrolactone embedded with a tetrahydropyran ring, and twenty total and formal syntheses of this natural product have been reported so far. This review summarizes the total and formal syntheses of neopeltolide and its analogues, highlighting the synthetic strategies exploited for constructing the tetrahydropyran ring. Full article
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