Rapid assembly of cyclopentene spiroisoindolinones <i>via</i> a rhodium-catalysed redox-neutral cascade reaction

Yuan, Ting‐Ting; Pi, Chao; You, Chang; Cui, Xiuling; Du, Sidong; Wan, Ting

doi:10.1039/c8cc08081j

Cited by 69 publications

(23 citation statements)

References 58 publications

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“…Yuan et al [52] reported ar edox-neutral Rh III catalyzed double CÀHb ond functionalization cascade to produce 3-spiros ubstituted isoindolinones from 2,3-diarylcyclopropenones and benzamide derivatives (Scheme 15). In this manner, two new CÀC bonds and one new CÀNb ond were formed with the indene substituent at C3 positiono ft he isoindolinone skeleton.…”

Section: Rh-catalyzed Olefination/alkylation-cyclizationmentioning

confidence: 99%

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Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Savela

Méndez-Gálvez

2021

Chemistry A European J

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Isoindolinone structure is an important privileged scaffold found in al argev ariety of naturallyo ccurring as well as synthetic, biologically and pharmaceutically active compounds. Owing to its crucial role in anumber of applications, the synthetic methodologies for accessingt his heterocyclic skeleton have received significant attentiond uring the past decade. In general, the synthetic strategies can be divided into two categories:F irst, direct utilization of phthalimides or phthalimidines as startingm aterials for the synthesis of isoindolinones;a nd second, construction of the lactam and/or aromatic rings by different catalytic methods, including CÀHa ctivation, cross-coupling,c arbonylation, condensation, addition and formal cycloaddition reactions. Especially in the last mentioned, utilization of transition metal catalysts provides access to ab road range of substituted isoindolinones.H erein, the recent advances (2010-2020) in transition metal catalyzed synthetic methodologies via formation of new CÀCbonds for isoindolinones are reviewed.

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Section: Rh-catalyzed Olefination/alkylation-cyclizationmentioning

confidence: 99%

“…Yuan et al [52] . reported a redox‐neutral Rh III catalyzed double C−H bond functionalization cascade to produce 3‐spiro substituted isoindolinones from 2,3‐diarylcyclopropenones and benzamide derivatives (Scheme 15).…”

Section: C−h Functionalization: Annulation/cyclizationmentioning

confidence: 99%

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Savela

Méndez-Gálvez

2021

Chemistry A European J

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“…Similar to C−H bond alkenylations (vide supra), the C−H bond activation step likely involved formation of a five‐membered metallacycle . This intramolecular cascade approach was later extended to different coupling partners (benzaldehydes, allylic alcohols, alkynes, diphenylcyclopropenone) leading to complex structures such as 3‐hydroxyisoindolin‐1‐ones, isoindolinones, cis ‐3,4‐dihydroisoquinolinones, and spiroisoindolinones (Scheme ) . Importantly, these examples show that the site‐selectivity of the catalysis is favored also because they lead to thermodynamically affordable five‐membered rings.…”

Section: C−c Bond‐forming Reactionsmentioning

confidence: 99%

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

Gramage‐Doria

2020

Chemistry A European J

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SelectiveC ÀHb ond functionalization catalyzed by metal complexes have completely revolutionized the wayi n which chemical synthesis is conceived nowadays. Typically, the reactivityo fat ransitionm etal catalyst is the key to control the site-, regio-and/or stereo-selectivity of aC ÀHb ond functionalization. Of particulari nterests are molecules that contain multiple CÀHb onds prone to undergo CÀHb ond activations with very similar bond dissociation energies at different positions. This is the case of benzanilides, relevant chemical motifs that are found in many useful fine chemicals, in which two CÀHs ites are present in chemically different aromatic fragments. In the last years, it has been found that depending on the metal catalyst and the reaction conditions, the amide motif might behave as ad irecting group towardst he metal-catalyzed CÀHb ond activation in the benzamide site or in the anilides ite. The impact and the consequences of such subtle control of site-selectivity are herein reviewed with important applicationsi ncarboncarbon and carbon-heteroatomb ond forming processes. The mechanisms unraveling these unique transformations are discussed in order to provide ab etter understanding for future developmentsi nt he field of site-selective CÀHb ond functionalization with transition metal catalysts.

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“…β-Thiocyanate alkenyl esters represent highly valuable multifunctional compounds because both alkenyl ester − and alkenyl thiocyanate − moieties are broadly utilized in various fields such as organic synthesis, pharmacy, and material science. Directly converting propargylic carboxylates into β-thiocyanate alkenyl esters through multicomponent reaction − represents a highly attractive transformation in organic synthesis, given the easily available raw materials. Recently, our group developed a novel method to synthesize various β-thiocyanate alkenyl esters in the range of 11–14:1 Z/E ratios from propargylic carboxylates via Brønsted acidic ionic liquid-catalyzed hydrothiocyanation of propargylic carboxylates .…”

Section: Introductionmentioning

confidence: 99%

Practical Approach for Clean Preparation of Z-β-Thiocyanate Alkenyl Esters

Lin

Shu

et al. 2019

ACS Sustainable Chem. Eng.

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A practical and eco-friendly method for the clean preparation of a variety of Z-β-thiocyanate alkenyl esters via lactic acid-catalyzed multicomponent hydrothiocyanation reaction was established. In the subgram-scale synthesis, Z-β-thiocyanate alkenyl esters were exclusively generated, and the product could be easily isolated in high purity via extraction. In the large-scale synthesis, the pure products could be simply collected through liquid–liquid separation. The eco-friendly lactic acid played a dual function in the transformation, serving as recyclable biomass catalyst and recyclable reaction medium.

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Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction

Abstract: A rhodium-catalysed redox-neutral cascade reaction starting from benzamides and cyclopropenones for the rapid assembly of cyclopentene spiroisoindolinones has been developed.

Cited by 69 publications

References 58 publications

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

Practical Approach for Clean Preparation of Z-β-Thiocyanate Alkenyl Esters

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