Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

Méndez-Gálvez, Carolina; Böhme, Matthias D.; Leino, Reko; Savela, Risto

doi:10.1002/ejoc.202000046

Cited by 10 publications

(7 citation statements)

References 109 publications

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“…In 2020, Savela and co-workers reported the preparation of isobenzofuranones and isoindolinones through cobalt-catalyzed [2+2+2] cycloaddition of 1,6-diynes with alkynes (Scheme 44). 105 The reaction used [CoCl 2 ] (10 mol%) and a sterically hindered tridentate pyridine-2,6diimine, i-PrPDI, as a ligand, in the presence of Zn (0.2 equiv) and ZnI 2 (0.3 equiv) at 100 °C in THF. Ester, methyl, phenyl, and alkyl substituents on the alkynes were well tolerated for this cobalt-catalyzed [2+2+2] cycloaddition of ester-or amide-tethered 1,6-diynes, delivering the corresponding isobenzofuranones and isoindolinones in 4-88% yield and regioselectivities varying from >99:1 to >1:99.…”

Section: Scheme 43mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.1 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion

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Section: Scheme 43mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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“…This could however be mitigated by dropwise addition of the diyne to the reaction mixture. Méndez‐Gálvez et al [191] . also utilized a similar approach with cobalt catalyst to afford N ‐unsubstituted isoindolinones, albeit only a few isoindolinone examples were reported (Scheme 100 B).…”

Section: Cycloaddition Cyclotrimerization and Annulation Reactionsmentioning

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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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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“…In most cases, vigilant workup is indispensable to avoid metal contamination due to the high coordination properties of products. 1,2 Due to the apparent demand for transition-metal-free, operationally simple, and cost-effective strategies, developing a simple Brønsted acid-catalyzed [2 + 2 + 2]-annulation reactions of alkynes is desirable. Although extensive literature on alkyne trimerization is present, only a few examples have been reported for transition-metal-free transformations, 3 which include thermal processes (temperature required is 100−600 °C), 4 micro-wave irradiation (needed specialty equipment), 5 aminemediated cyclotrimerization of propargylic ketones, 6 lactic-acidinduced trimerizations of enaminone 7 and intramolecular hexadehydro-Diels−Alder reaction (HDDA) of tethered enetetraynes.…”

Section: Introductionmentioning

confidence: 99%

“…12 As discussed above, carbonyl compounds 2 also serve as versatile building blocks for benzannulation reactions and are known to produce diverse benzenoid scaffolds under diverse catalytic conditions. 2 In recent times, there has been an upsurge in the research involving alkynes as carbonyl compounds surrogates, which are ambiphilic in nature, participate in fascinating cascade trans- formations (through transition metal/Lewis acid/Brønsted acid-catalyzed π-activation), and deliver synthetically challenging complex scaffolds more straightforwardly. 13 Herein, we unveiled the potential of alkynyl alcohols (known to generate cyclic enol ethers, which are carbonyl equivalents) as [2 + 2 + 2]and [2 + 3]-annulation partners.…”

Section: Introductionmentioning

confidence: 99%

Divergent Synthesis of Oxepino-Phthalides and [5,5]-Oxaspirolactones through [2 + 2 + 2]- and [2 + 3]-Annulation of Alkynyl Alcohols with α-Ynone-Esters

Kambale,

Borade,

Vinodkumar

et al. 2023

J. Org. Chem.

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Unmasking the synthetic potential of alkyne functional group of alkynyl alcohols as surrogates of carbonyl compounds, herein we present the first Brønsted acid (TfOH)-catalyzed [2 + 2 + 2]-annulation of 4-pentyn-1-ols (possessing terminal alkyne) with α-ynone-esters to access tricyclic tetrahydro-oxepino-phthalides. Besides, an unprecedented synthesis of αacetoaryl or α-alkynyl [5,5]-oxaspirolactones has been demonstrated by employing 4-pentyn-1-ols (possessing an internal alkyne) as an annulation partner, which proceeds through a divergent [2 + 3]-annulation pathway.

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Synthesis of Isobenzofuranones by Cobalt Catalyzed [2+2+2] Cycloaddition

Cited by 10 publications

References 109 publications

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

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

Divergent Synthesis of Oxepino-Phthalides and [5,5]-Oxaspirolactones through [2 + 2 + 2]- and [2 + 3]-Annulation of Alkynyl Alcohols with α-Ynone-Esters

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