Palladium(0)-catalyzed [4+2] Annulation of Salicylaldehydes and Propargyl Carbonates to Produce 3,4-Dihydro-2-methylene-2<i>H</i>-1-benzopyran-4-ols

Kawase, Ayumu; Omura, Hirofumi; Doi, Takayuki; Tsukamoto, Hirokazu

doi:10.1246/cl.190642

Cited by 5 publications

(2 citation statements)

References 97 publications

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“…As a common structural unit of oxygen-containing heterocyclic compounds in natural products, the benzopyranoid skeleton exhibits high biological activity . 4 H -Chromene and 2,8-dioxabicyclo[3.3.1]nonane are a pair of benzopyranoid isomers.…”

Section: Introductionmentioning

confidence: 99%

Controllable Synthesis of Two Isomers 4H-Chromene and 2,8-Dioxabicyclo[3.3.1]nonane Derivatives under Catalyst-Free Conditions

et al. 2021

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A one-pot method for the selective synthesis of two isomers 4H-chromene and 2,8-dioxabicyclo[3.3.1]nonane derivatives was developed without a catalyst and using EtOH/H2O (4:1, v/v) as the solvent. The reaction was conducted under mild conditions, with forming multiple chemical bonds in one pot and high atom economy, and only a stoichiometric amount of H2O is produced as the byproduct. Its selectivity was controlled by thermodynamics and kinetics, and the reasons for the transformation of the two structures are also discussed.

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Section: Introductionmentioning

confidence: 99%

Controllable Synthesis of Two Isomers 4H-Chromene and 2,8-Dioxabicyclo[3.3.1]nonane Derivatives under Catalyst-Free Conditions

et al. 2021

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“…Pd-catalyzed decarboxylative alkenylation: Many examples exist in the literature of propargylic electrophiles reacting with nucleophiles in the presence of a palladium catalyst to produce alkenylated products. − The explanation for why this alkenylation pathway is more prominent than the previously described pathways can be rationalized by the nature of the palladium-propargyl intermediate. The η 3 -π-propargylpalladium intermediate has been shown to react readily at the central carbon followed promptly by a protonation event to give a highly reactive η 3 -π-allylpalladium, which, in the presence of a second nucleophile will furnish the alkenylated product.…”

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confidence: 99%

Advances in Decarboxylative Palladium-Catalyzed Reactions of Propargyl Electrophiles

O’Broin

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2020

J. Org. Chem.

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The propargyl electrophile has proven to be a versatile reactant when coupled with palladium catalysis. Its versatility is owed to the several reaction pathways that the palladium-propargyl intermediate can proceed by, and the outcome can be predictably controlled by varying several factors. The tunable nature of the propargyl electrophile along with its versatility are detailed herein. The initial reports for each of the pathways are highlighted along with a discussion of more recent developments in the field.

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Palladium‐Catalyzed [4+2] and [5+2] Annulation for the Synthesis of Tetrahydroquinolines and 1,4‐Benzoxazepines

Zhang

et al. 2020

Eur J Org Chem

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and [5+2] annulations of propargyl carbonates with malonate-tethered anilines and 2aminobenzylic alcohols were developed, giving the correspond-Tetrahydroquinoline and benzoxazepine derivatives are ubiquitous structural motifs in numerous bioactive products and pharmaceuticals (Figure 1). [1] Consequently, significant attention has been devoted to the synthesis of these molecules. Many synthetic methods for tetrahydroquinolines have been developed, including hydrogenation of quinolines, [2] aza-Diels-Alder reactions, [3] and Reissert-type reactions. [4] Benzoxazepines can be accessed by Beckmann or Schmidt rearrangements, [5] transition-metal catalyzed cross-coupling. [6] [a] Dr.

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Palladium(0)-catalyzed [4+2] Annulation of Salicylaldehydes and Propargyl Carbonates to Produce 3,4-Dihydro-2-methylene-2H-1-benzopyran-4-ols

Cited by 5 publications

References 97 publications

Controllable Synthesis of Two Isomers 4H-Chromene and 2,8-Dioxabicyclo[3.3.1]nonane Derivatives under Catalyst-Free Conditions

Controllable Synthesis of Two Isomers 4H-Chromene and 2,8-Dioxabicyclo[3.3.1]nonane Derivatives under Catalyst-Free Conditions

Advances in Decarboxylative Palladium-Catalyzed Reactions of Propargyl Electrophiles

Palladium‐Catalyzed [4+2] and [5+2] Annulation for the Synthesis of Tetrahydroquinolines and 1,4‐Benzoxazepines

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