Synthesis of 3,4-Dihydroisocoumarins via Palladium-Catalyzed Coupling of Vinylic Halides or Triflates with<i>o</i>-(1-Alkenyl)benzoic Acids

Larock, Richard C.; Yang, Hoseok

doi:10.1055/s-1994-22996

Cited by 25 publications

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“…The intermolecular reaction of o -(1-alkenyl)benzoic acids with vinylic halides and triflates in the presence of a palladium catalyst produces the corresponding 3,4-dihydroisocoumarins (Scheme ) . For example, the treatment of o -vinylbenzoic acid ( 211 ) and a vinylic halide such as 212 afforded the dihydroisocoumarin 213 in a 70% yield.…”

Section: 4 Heterocycles Via Intermolecular Annulationmentioning

confidence: 99%

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Synthesis of Heterocycles via Palladium-Catalyzed Oxidative Addition

2006

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Section: 4 Heterocycles Via Intermolecular Annulationmentioning

confidence: 99%

“…78 The intermolecular reaction of o-(1-alkenyl)benzoic acids with vinylic halides and triflates in the presence of a palladium catalyst produces the corresponding 3,4-dihydroisocoumarins (Scheme 80). 79 produced. This is consistent with the formation of a π-allylpalladium intermediate.…”

Section: Heterocycles Via Intermolecular Annulationmentioning

confidence: 99%

Synthesis of Heterocycles via Palladium-Catalyzed Oxidative Addition

2006

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“…Trans-stilbenoids also form the backbones of organic probes 17 for cation sensing, photovoltaic solar cells, 18 light emitting diodes 19 (LEDs), organogels 20 and recognition probes 21 of disaccharides. Additionally, they serve as the precursors for 3,4-dihydroisocoumarins, 22 substituted phthalides 23 and oligoresveratrols. 24 Commercially, Res (1) is produced from the roots of Polygonum cuspidatum, a Chinese plant used in folk medicine.…”

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confidence: 99%

Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides

Mitra

Shome

et al. 2012

Org. Biomol. Chem.

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The synthesis of stilbenoids and styryl carboxylic acids is accomplished with high E-stereoselectivity by olefination of aldehydes with thiophthalides under basic conditions. The olefination is highly atom-efficient as it only loses elemental sulfur during the reaction. This olefination, in conjunction with retro Kolbe-Schmitt reaction, allows facile synthesis of E-hydroxystilbenoids with minimal employment of protecting groups. This study also discloses two important findings: formation of i) 4-methylsulfanyl isocoumarins and ii) an 2-arylindenone.

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“…Baik and Hong recently reported that internal alkenes can be used in this Pd-catalyzed 1,1-aryloxygenation with the assistance of a directing group. 8 In addition to 1,1-aryloxygenation, the Pdcatalyzed 1,1-alkenyloxygenation of 2-vinylbenzoic acids with alkenyl halides was reported by Larock, 9 which led to the production of 3-alkenylated lactones. In this reaction, the scope of the carbon functionalities that can be introduced is limited to an alkenyl moiety.…”

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confidence: 99%