Molecular Diversity of Cyclooctatetraenes through Palladium‐Catalyzed Cascade Reactions

Blouin, Sarah; Pertschi, Romain; Schoenfelder, Angèle; Suffert, J.; Blond, Gaëlle

doi:10.1002/adsc.201800110

Cited by 10 publications

(3 citation statements)

References 34 publications

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“…When the tether was extended by one carbon, however, conversion was extremely low and no tropone was observed (Scheme ), and most of the starting material could be recovered. Such results have already been observed, notably in our group during cyclocarbopalladation reactions . This indicates that the extended distance between the rhodium in intermediate B or C and the third alkyne likely hampers the chelation of the latter to the metal, leading to a very sluggish reaction.…”

supporting

confidence: 71%

“…Such results have already been observed, notably in our group during cyclocarbopalladation reactions. 36 This indicates that the extended distance between the rhodium in intermediate B or C and the third alkyne likely hampers the chelation of the latter to the metal, leading to a very sluggish reaction. As both 2t and 3t compounds are aromatic, we can speculate that they have a similar stability, making it complicated to rationalize the sole formation of the benzenoid compound without extensive calculations.…”

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confidence: 99%

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Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

et al. 2018

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confidence: 71%

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confidence: 99%

Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

et al. 2018

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“…More recently, Suffert, Blond, and co-workers envisioned the access to the cyclooctatetraene core from the reaction of alkenyl bromides IV with arylboronic acids through a polycyclization cascade process involving three alkyne moieties (Scheme 39). 114 Substrate IV undergoes two cyclocarbopalladations, first a 4-exo-dig and then a 5-exo-dig cyclization, providing intermediate V. Then, an 8π-electrocyclization followed by a 1,3 π-allyl palladium shift takes place ended by a Suzuki cross-coupling to yield the final cyclooctatetraene product. Different electron-rich and electron-poor arylboronic acids could be installed in the final cyclic structure, as well as heteroaromatic boronic acids including those containing basic nitrogen atoms.…”

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confidence: 99%

Transition-Metal-Catalyzed Functionalization of Alkynes with Organoboron Reagents: New Trends, Mechanistic Insights, and Applications

et al. 2021

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Catalytic functionalization of alkynes with organoboron reagents provides a straightforward access to stereochemically defined multisubstituted alkenes, which are structural motifs commonly found in bioactive compounds and organic materials. Recent progress has substantially broadened the scope of this field on several fronts. Strategies for regioselectivity control in the 1,2-migratory insertion across unsymmetrical internal alkynes, as well as for the direct access to products with anti-insertion stereochemistry, have been devised. The alkenyl-to-aryl 1,4-metal migration upon metal insertion has been recently exploited in powerful cascade sequences leading to complex polycyclic scaffolds, including the development of enantioselective processes. Elegant enantiospecific and dynamic kinetic resolution methods have been developed for accessing chiral allenes from propargylic alcohol derivatives. Mechanistic manifolds have emerged based on single-electron transfer (SET) that have provided a fresh impetus for alkyne 1,2-difunctionalization with complementary stereoselectivity to processes relying on 1,2-insertion of R–M species. Herein, we discuss the most recent advances in transition-metal-catalyzed functionalization of alkynes using organoboron reagents, categorized according to the type of mechanistic outcome. Emphasis is placed on mechanistic aspects, synthetic utility, limitations, and challenges for future research.

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A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction

et al. 2019

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We report an unprecedented domino polycyclization from readily available 2,4‐dienals and cyclic α,β‐unsaturated imines that is initiated by an iso‐Nazarov reaction. This Brønsted acid promoted reaction enables the concomitant formation of four bonds, three cycles, and four contiguous stereogenic centers to yield elaborated structures in a single operation. A range of fused hexacyclic molecules is obtained in a highly diastereoselective manner.

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Molecular Diversity of Cyclooctatetraenes through Palladium‐Catalyzed Cascade Reactions

Abstract: No Abstract

Cited by 10 publications

References 34 publications

Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes

Transition-Metal-Catalyzed Functionalization of Alkynes with Organoboron Reagents: New Trends, Mechanistic Insights, and Applications

A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction

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