The use of palladium catalysts in fused ring synthesis has been increasingly noteworthy in recent years in organic synthesis. It has a lot of potential compared to other transition metal catalysts, because of its one-of-a-kind feature that makes them more widely applicable in a variety of disciplines application. Palladium is important in a variety of Heck processes, including intramolecular, intermolecular, and reductive Heck reactions, which produce diverse carbocycles and heterocycles of biological importance. Under optimal reaction conditions, carbocyclization or heterocyclization occurs, resulting in the production of numerous structural building blocks of naturally occurring compounds. Beside intramolecular Heck-type reactions, cycloaddition, cycloalkylation, oxidative coupling, C-H functionalization, cross-coupling reactions, and carboamidation reactions have also been employed extensively to access fused carbo- and heterocycles of immense biological importance. This review article provides a well-summarized discussion (since 2001) on fused carbo- and heterocycle ring synthesis using palladium catalysts, overviewing their applications, and mechanistic insights.
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http://dx.doi.org/10.1002/asia.202200725 | DOI Listing |
IUCrdata
November 2024
School of Chemistry and Physics, University of KwaZulu-Natal, Westville campus, Private bag X54001, Durban, 4000, South Africa.
The crystal structure of the title compound, CHNOS, reveals two symmetrically independent mol-ecules within the asymmetric unit. Each mol-ecule contains a chromenone core attached to a 2-thio-phene ring, cyano, and amino groups. The 2-thio-phene ring of one of the two mol-ecules in the asymmetric unit was found to be disordered over two positions, with the major component having a site occupancy factor of 0.
View Article and Find Full Text PDFChem Commun (Camb)
November 2024
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
Macrocyclization the intramolecular Alder-ene reaction of arynes to construct carbo- and hetero-macrocycles fused with an indoline or isoindoline moiety is described. By installing ether, ester, alkene, and cyclic tethers at an appropriate location between the aryne and the ene donor, macrocycles up to a 46-membered ring could be constructed.
View Article and Find Full Text PDFBioorg Chem
December 2024
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, 11884 Cairo, Egypt; Chemistry Department, Faculty of Science, Al-Baha University, Al-Baha 1988, Saudi Arabia.
The 8-aryl-, 8-styryl- and 8-arylethynyl substituted 5-methoxyflavones were synthesized and characterized using a combination of spectroscopic techniques. Single crystal X-ray diffraction (XRD) study on a representative compound 3h shows an inverted dimer linked by fused ten and six-membered ring motifs involving intermolecular CO⋯HC and CH⋯OC hydrogen bonds. Compounds 3b, 3c, 3d, 4a and 4b exhibited strong activity against the human breast (MCF-7) cancer cell line (IC = 13.
View Article and Find Full Text PDFJ Org Chem
January 2024
Aix Marseille Université, CNRS, Centrale Méditerranée, ISM2, 13397 Marseille, France.
Recently, the synthesis of the racemate of an overcrowded triply fused carbo[7]helicene of formula CH with three carbo[7]helicenes fused within a central six-membered ring was described. This molecule was found to embed an extremely contorted central six-membered ring and two negative curvatures. We report herein the resolution of the corresponding enantiomers and their conformational, structural, photophysical, and chiroptical properties.
View Article and Find Full Text PDFOrg Lett
December 2023
Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, 402 North Blackford Street, Indianapolis, Indiana 46202, United States.
The divergent organophotoredox-catalyzed radical cascade annulation reactions of 1,6-enynes were developed. A series of cyclopropane-fused hetero- and carbo-bicyclic, tricyclic, and spiro-tetracyclic compounds were facilely synthesized from a broad scope of 1,6-enynes and 2,6-lutidine -oxide under mild and metal-free conditions with blue light-emitting diode light irradiation. The cascade annulation reaction occurs with the intermediacy of a β-oxyvinyl radical, which is produced from photocatalytically generated pyridine -oxy radical addition to the carbon-carbon triple bond.
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