Silver‐Catalysed Domino Approach to 1,3‐Dicarbo‐Substituted Isochromenes

Dell’Acqua, Monica; Pirovano, Valentina; Peroni, S.; Tseberlidis, Giorgio; Nava, Donatella; Rossi, Elisabetta; Abbiati, Giorgio

doi:10.1002/ejoc.201601602

Cited by 19 publications

(6 citation statements)

References 37 publications

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“…The asymmetric addition reactions of C-nucleophiles to isobenzopyrylium ions at the 1-position provided a straight route to structurally diverse chiral 1-substituted 1H-isochromene derivatives. [102][103][104] In 2016, the Enders group demonstrated the type of asymmetric addition could be realized under a combination of Ag2CO3 and chiral phosphoric acid, but only with moderate success (Scheme 10a). 105 Just Peng and his co-workers disclosed an efficient asymmetric addition of isobenzopyrylium with diazomethylphosphonate as Cnucleophile (Scheme 10b).…”

Section: Asymmetric Nucleophilic Additionmentioning

confidence: 99%

Asymmetric reactions involving isobenzopyrylium ion intermediates

Lan¹,

Yu²,

Qian³

et al. 2021

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Isobenzopyrylium ions are highly reactive intermediates which have wide applications in synthetic chemistry. A range of catalytic reactions based on isobenzopyrylium, such as 1,2-nucleophilic addition, [4+2] and [3+2] cycloaddition provide a powerful protocol for constructing complex natural and unnatural products. Their asymmetric variations have been less explored, possibly owing to the lack of coordination sites within their planar structures. This mini-review summarizes the asymmetric transformations developed involving isobenzopyrylium ion intermediates. These works are arranged according to the reaction types. The catalytic systems and reaction mechanisms are described.

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Section: Asymmetric Nucleophilic Additionmentioning

confidence: 99%

Asymmetric reactions involving isobenzopyrylium ion intermediates

Lan¹,

Yu²,

Qian³

et al. 2021

Arkivoc

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“…Silver(I) complexes are endowed with both a σ‐philic and π‐philic character . Silver(I) triflate was reported to be quite effective in the domino intramolecular cyclisation of 2‐alkynylacetophenones . The increased solubility and the enhanced thermodynamic stabilities of macrocyclic complexes were exploited to synthesise 3‐substituted 1‐alkoxyisochromenes in a stereoselective manner from 2‐alkynylbenzaldehydes and alcohols as nucleophiles in the presence of silver(I) complexes of Pc‐L ligands 30 .…”

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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“…For many years, we have been interested in the study of new valuable approaches for the synthesis of oxygen containing heterocycles starting from alkyne derivatives . In this context, we recently reported a AgOTf/ p ‐TSA co‐catalyzed synthesis of 3,4‐fused 2‐pyranones, mainly isocoumarins, starting from 2‐alkynyl‐(hetero)arylcarboxylates characterized by mild reaction conditions, high yields and selectivity, low catalysts loading .…”

Section: Introductionmentioning

confidence: 99%

p‐TSA‐Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2‐Alkynyl‐(hetero)‐arylcarboxylates: an Alternative Access to 6‐Substituted 3,4‐Fused 2‐Pyranones

et al. 2019

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In this paper, we describe the use of p‐TSA based Deep Eutectic Solvents (DESs) as alternative environmental‐friendly “active” solvents for the microwave‐mediated synthesis of 6‐substituted 3,4‐fused 2‐pyranones, and in particular isocoumarins, starting from 2‐alkynyl‐(hetero)arylcarboxylates. When the alkyne terminus bears a neutral or an electron‐donating group (EDG), the reactions are fast, clean and highly regioselective, to give the 6‐endo‐dig cyclization products in good to excellent yields. For substrates bearing an electron‐withdrawing group (EWG) on the alkyne end, the regioselectivity can be tuned by adding a small amount of silver(I) triflate as co‐catalyst. DES was demonstrated to be reusable without loss of efficiency in terms of reaction yields. Based on experimental evidence and previous findings, two competitive mechanisms working simultaneously are proposed to explain the outcomes and the regioselectivity issues.

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Silver‐Catalysed Domino Approach to 1,3‐Dicarbo‐Substituted Isochromenes

Cited by 19 publications

References 37 publications

Asymmetric reactions involving isobenzopyrylium ion intermediates

Asymmetric reactions involving isobenzopyrylium ion intermediates

Catalytic Applications of Pyridine‐Containing Macrocyclic Complexes

p‐TSA‐Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2‐Alkynyl‐(hetero)‐arylcarboxylates: an Alternative Access to 6‐Substituted 3,4‐Fused 2‐Pyranones

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