From domino to multicomponent: synthesis of dihydroisobenzofurans

Dell’Acqua, Monica; Facoetti, Diego; Abbiati, Giorgio; Rossi, Elisabetta

doi:10.1016/j.tet.2010.12.056

Cited by 29 publications

(11 citation statements)

References 49 publications

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“…Dihydroisobenzofurans have been synthesized by a palladium‐catalyzed domino addition/annulation process of ortho ‐alkynylbenzaldehydes in the presence of alcohols as nucleophiles 6b,20,21. More recently, a variety of substituted dihydroisobenzofurans have been synthesized by a one‐pot three component Pd(0)/Cu(I)‐catalyzed domino reaction of o ‐bromobenzaldehydes, methanol and terminal alkynes under microwave irradiation 22. As depicted in Table 5, oxime palladacycle 1a in the presence of Xphos as ligand, is an excellent catalytic system for the synthesis of 3‐methoxy‐1,3‐dihydroisobenzofurans from 2‐bromobenzaldehydes via multicomponent reaction with the solvent and terminal alkynes.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Dihydroisobenzofurans via Palladium‐Catalyzed Sequential Alkynylation/Annulation of 2‐Bromobenzyl and 2‐Chlorobenzyl Alcohols under Microwave Irradiation

Buxaderas¹,

Alonso²,

Nájera³

2014

Adv Synth Catal

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The palladium-catalyzed synthesis of dihydroisobenzofurans has been performed by sequential Sonogashira cross-coupling/cyclization reactions between terminal alkynes and 2-(hydroxymethyl)bromo-and chlorobenzenes in methanol as solvent at 130 8C under microwave irradiation. A 4,4'-dichlorobenzophenone oxime-derived chloro-bridged palladacycle is an efficient pre-catalyst to perform this tandem process using 2-dicyclohexylphosphanyl-2',4',6'-triisopropylbiphenyl (Xphos) as ancillary ligand and potassium hydroxide as base in the ab-sence of a copper cocatalyst. Under these conditions, functionalized 2-bromo-and 2-chlorobenzaldehydes are also suitable partners in the domino process affording phthalans in good yields. All the reactions can be performed under air and employing reagentgrade chemicals under low loading conditions (1 mol% Pd). Scheme 1. Sonogashira coupling and/or intramolecular hydroalkoxylation towards 1,3-dihydroisobenzofurans.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Dihydroisobenzofurans via Palladium‐Catalyzed Sequential Alkynylation/Annulation of 2‐Bromobenzyl and 2‐Chlorobenzyl Alcohols under Microwave Irradiation

Buxaderas¹,

Alonso²,

Nájera³

2014

Adv Synth Catal

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“…Finally, in connection with the interest in the study of metal‐catalysed domino and multicomponent processes of alkynes, carbonyl compounds and amines, Caselli, Abbiati and co‐workers showed that the well‐defined silver(I)–Pc‐L complexes were able to promote efficient coupling of aldehydes, terminal alkynes and amines (A 3 ‐coupling) to yield propargylamines (Scheme ) . The use of microwave heating allowed a lower catalyst loading (3 mol‐%), a reduced ratio of the three starting reagents in short reaction times (5 min) and a broad reaction scope, including arene/alkanecarbaldehydes, aryl/alkylacetylenes and secondary aliphatic amines.…”

Section: C–c and C–o Bond‐forming Reactionsmentioning

confidence: 99%

Catalytic Applications of Pyridine‐Containing Macrocyclic Complexes

2017

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The introduction of a pyridine moiety into the skeleton of a polyazamacrocyclic ligand affects both the thermodynamic properties and the coordination kinetics of the resulting metal complexes. These features have attracted great interest from the scientific community in recent years. The field of application of pyridine‐containing macrocyclic ligands ranges from biology to supramolecular chemistry, encompassing MRI, molecular recognition, materials and catalysis. In this microreview we provide a perspective of the catalytic applications of metal complexes of pyridine‐containing macrocycles, including an account of investigations from the authors' laboratories dealing with stereoselective C–C and C–O bond‐forming reactions. The increased conformational rigidity imposed by the pyridine ring allowed for the isolation and characterisation of metal complexes in high oxidation states and the study of their relevance in oxidation reactions. On the other hand, the very different conformations accessible upon the metal coordination and the easily tuneable synthesis of the macrocyclic ligands have been exploited in stereoselective synthesis.

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“…Owing to their great importance, there has been a continuous interest in developing new and efficient methods for the synthesis of such heterocycles. Several procedures are based on the palladium-promoted cyclization of suitable substrates, such as benzaldehydes [56], benzyl [57][58][59][60] and homobenzyl alcohols [61,62], propargyl ethers [63][64][65][66][67][68], benzylethers [58] and benzylamines [69], anilines [70], propargylamides [71], and arylimides [72].…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

2021

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Supported catalysts are important tools for developing green-economy-based processes. Palladium nanoparticles (NPs) that are immobilized on two fibers developed as metal scavengers (i.e., Smopex®-234 and Smopex®-111, 1% w/w) have been prepared and tested in copper-free cyclocarbonylative Sonogashira reactions. Their catalytic activity has been compared with that of a homogeneous catalyst (i.e., PdCl2(PPh3)2). Pd/Smopex®-234 showed high activity and selectivity in the synthesis of functionalized heterocycles, such as phthalans and isochromans, even when working with a very low amount of palladium (0.2–0.5 mol%). The extension of Pd/Smopex®-234 promoted cyclocarbonylative reactions to propargyl and homopropargyl amides afforded the corresponding isoindoline and dihydrobenzazepine derivatives. A preliminary test on Pd NPs leaching into the solution (1.7 × 10−3 mg) seems to indicate that, at the end of the reaction, almost all of the active metal is present on the fiber surface.

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From domino to multicomponent: synthesis of dihydroisobenzofurans

Cited by 29 publications

References 49 publications

Synthesis of Dihydroisobenzofurans via Palladium‐Catalyzed Sequential Alkynylation/Annulation of 2‐Bromobenzyl and 2‐Chlorobenzyl Alcohols under Microwave Irradiation

Synthesis of Dihydroisobenzofurans via Palladium‐Catalyzed Sequential Alkynylation/Annulation of 2‐Bromobenzyl and 2‐Chlorobenzyl Alcohols under Microwave Irradiation

Catalytic Applications of Pyridine‐Containing Macrocyclic Complexes

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

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