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Pd-catalysed C-H bond functionalisation route to 1,2-dihydroferroceno[]isoquinoline and its annellated derivatives and the reactivity of these compounds.
Dalton Trans
January 2025
Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 00 Prague, Czech Republic.
C-H bond functionalisation has developed into a powerful synthetic methodology that is applicable to a wide array of substrates, including organometallic compounds. In this study, racemic, planar-chiral 1,2-dihydroferroceno[]isoquinoline and analogous helical compounds with one or two additional -fused benzene rings were synthesised by palladium-catalysed C-H bond activation/cyclisation of -[(bromoaryl)methyl]--(methylsulfonyl)aminoferrocenes. These starting materials are readily accessible from FcNHSOMe (Fc = ferrocenyl) and appropriate vicinal bromo-(bromomethyl)arenes.
View Article and Find Full Text PDFChlorobenzene-driven palladium-catalysed lactonisation of benzoic acids.
RSC Adv
January 2024
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women's University 11-68, 9-Bancho, Koshien Nishinomiya Hyogo 663-8179 Japan
Herein, we developed a palladium-catalysed C-H cyclisation of benzoic acids in chlorobenzene without additional oxidants. The key to the success of these reactions is the use of chlorobenzene, which serves a dual role as a solvent and an oxidant, thus providing a simple and efficient method for synthesising phthalides.
View Article and Find Full Text PDFSynthetic Study toward Triterpenes from the Family of Natural Products.
Molecules
May 2023
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK.
Triterpenoid natural products from the family have long presented a significant synthetic challenge. Lancifodilactone I, a member of the family not previously synthesized, was identified as a key natural product target, from which many other members could be synthesized. We envisaged that the core ring system of lancifodilactone I could be accessed by a strategy involving palladium-catalysed cascade cyclisation of a bromoenynamide, via carbopalladation, Suzuki coupling and 8π-electrocyclisation, to synthesize the core 7,8-fused ring system.
View Article and Find Full Text PDFPd-catalysed intramolecular transformations of indolylbenzenesulfonamides: -sulfonamido-bi(hetero)aryls C2-arylation and polycyclic sultams C3 arylation.
Org Biomol Chem
November 2022
School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India.
Palladium-catalysed and base-dependent intra-molecular -substitution and cyclisation strategies involving -indolyl-substituted aryl-sulfonamides for the rapid construction of 2-aryl indole and indole-fused six-membered sultams are described. The Pd(OAc)/PhP/EtN combination delivers indolyl C2 arylated motifs C(2)-N bond cleavage followed by C-C bond formation. In sharp contrast to this, the Pd(OAc)/PhP/KCO combination induced intramolecular-Heck cross-coupling affords polycyclic sultams exclusively.
View Article and Find Full Text PDFPalladium-catalysed cyclisation of ynamides and propargyl tethered iodosulfonamides with boronic acids leading to benzosultams.
Org Biomol Chem
August 2021
School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India.
An efficient and straightforward Pd-catalysed synthesis of diversely substituted sultams utilising ynamides and boronic acids is disclosed; toluene was found to be the most suitable solvent for this transformation. This strategy has been successfully applied to generate dihydrobenzo[d]isothiazole 1,1-dioxides and dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxides. The advantages of this protocol are good functional group tolerance, broad substrate scope, high-yielding reaction and low catalyst loading to access benzofused sultams with five-/six-membered rings.
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