Synthesis of 3-substituted isoindolin-1-ones via a palladium-catalysed 3-component carbonylation/amination/Michael addition process

Gai, Xinjie; Grigg, Ronald; Khamnaen, Tossapol; Rajviroongit, Shuleewan; Sridharan, Visuvanathar; Zhang, Lixin; Collard, Simon; Keep, Ann

doi:10.1016/j.tetlet.2003.08.036

Cited by 50 publications

(18 citation statements)

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“…Recently, the same group also described a novel palladium-catalyzed carbonylative synthesis of isoindolin-1-ones. 157 This three-component cascade process involved the carbonylation of substituted aryl iodides to generate the respective acyl palladium species, which reacted with a primary aliphatic/ aromatic amine, amide, or sulfonamide followed by an intramolecular conjugate addition to afford 3-substituted isoindolin-1-ones in good yields (Scheme 46c). Moreover, Shim and co-workers described the cyclocarbonylation of 2-(2-bromophenyl)-2-oxazolines by a palladium−nickel catalyst.…”

Section: Palladium-catalyzed Carbonylative Synthesis Of Five-memberedmentioning

confidence: 99%

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

2012

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Besides the mentioned processes, palladium-catalyzed carbonylation of alkynols represents another powerful methodology for the preparation of lactones. As early as in 1994, Gabriele and co-workers presented a PdI 2 /KI-catalyzed oxidative carbonylation of α-substituted hydroxyalkynes to four-membered lactones in good yields under mild conditions. Later on, they extended this methodology to but-3-yn-1-ols for the synthesis of five-membered lactones (Scheme 4a). 13 Scheme 1. Selected Examples of Heterocyclic Drugs Scheme 2. Palladium-Catalyzed Carbonylative Synthesis of Lactones Scheme 3. Palladium-Catalyzed Carbonylative Synthesis of Lactones from Alkenyloxiranes Scheme 4. Palladium-Catalyzed Carbonylative Synthesis of Lactones from Alkynols Chemical Reviews Review dx.

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Section: Palladium-catalyzed Carbonylative Synthesis Of Five-memberedmentioning

confidence: 99%

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

2012

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“…These transformations proceed via Cu-catalyzed Michael addition/cyclization to afford allylsulfone 69, which undergoes intermolecular Pd-catalyzed allylic substitution to provide the observed product. Balme sequential Pd-catalyzed processes involving Michael addition/cross-coupling events have been reported by Grigg (eq 105) [145]. The potential power of multicomponent strategies is illustrated in a recent one-pot, four-component synthesis of tetrahydro-β−carbolines [146].…”

Section: Heterocycle Synthesis Via Multicomponent Coupling Strategiesmentioning

confidence: 94%