Oxidative Arylation of Isochroman

Park, Soo J.; Price, Jason R.; Todd, Matthew H.

doi:10.1021/jo2021373

Cited by 99 publications

(31 citation statements)

References 58 publications

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“…[196a] Under these conditions,anisole derivatives were smoothly benzhydrylated to afford the corresponding triarylmethane derivatives in moderate to excellent yields (Scheme 74). [197] Oxidation of the anisole derivatives to Thelast section of this Review will finally cover developments in the direct alkylation of simple arenes using less conventional alkylating reagents. More recently,the transition-metal-free direct benzylation of electron-deficient simple arenes has also been reported using only potassium tert-butoxide as promoter at room temperature.…”

Section: Alkylation By Cross-dehydrogenative Coupling With Alkanes Ementioning

confidence: 99%

“…[196b] Finally,t he direct cross-dehydrogenative coupling of chromans with anisole derivatives could be promoted by using ac ombination of CuCl 2 and DDQ to afford the corresponding arylated chromans in low to good yields (Scheme 75). [197] Oxidation of the anisole derivatives to generate aryl radicals and their subsequent addition to intermediate oxonium ions would account for this transformation.…”

Section: Alkylation By Cross-dehydrogenative Coupling With Alkanes Ementioning

confidence: 99%

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Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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The alkylation of arenes is one of the most fundamental transformations in chemical synthesis leading to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene: these methods however suffer from limitations in scope, efficiency and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group facilitating, in the presence of a metal catalyst, the regioselective alkylation of a C-H bond. These directed alkylations of C-H bonds in arenes are overviewed, in a comprehensive manner, in this review article.

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Section: Alkylation By Cross-dehydrogenative Coupling With Alkanes Ementioning

confidence: 99%

Section: Alkylation By Cross-dehydrogenative Coupling With Alkanes Ementioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

View full text Add to dashboard Cite

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“…Finally, the direct cross‐dehydrogenative coupling of chromans with anisole derivatives could be promoted by using a combination of CuCl 2 and DDQ to afford the corresponding arylated chromans in low to good yields (Scheme ) . Oxidation of the anisole derivatives to generate aryl radicals and their subsequent addition to intermediate oxonium ions would account for this transformation.…”

Section: Alkylation Of Simple Arenesmentioning

confidence: 99%

Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

Evano

Theunissen

2019

Angew Chem Int Ed

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Alkylated arenes are ubiquitous molecules and building blocks commonly utilized in most areas of science where there is a need for small organic molecules. Despite its apparent simplicity, the regioselective alkylation of arenes is still a challenging transformation in a lot of cases. Classical methods for the introduction of alkyl groups on arenes, which include the venerable Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene, as well as alternatives such as the directed alkylation of C-H bonds, still suffer from severe limitations in terms of scope, efficiency and selectivity. This can be addressed by exploiting the innate reactivity of some (hetero)arenes, in which electronic and steric properties, governed (or not) by the presence of one (or multiple) heteroatom(s) ensure high levels of regioselectivity. These innate alkylations of C-H bonds in (hetero)arenes will be overviewed, in a comprehensive manner, in this review article.

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“…[45] Interessanterweise zeigte die Gruppe von Todd, dass die CuCl 2 /DDQ-katalysierten Arylierungen von Isochromanen mit Anisolen über die Bildung von Arylradikalen und nicht über die erwartete Friedel-Crafts-Reaktion ablaufen. [46] Schema 24. Verbesserte Minisci-Alkylierungen von Heterocyclen.…”

Section: Methodsunclassified

Dehydrierende Kreuzkupplungen von C‐H‐Bindungen: vielseitige Verfahren zur Bildung von C‐C‐Bindungen

2013

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In den vergangenen zehn Jahren wurde eine beeindruckende Zahl an Verfahren entwickelt, die den selektiven Aufbau von C‐C‐Bindungen über die direkte Verknüpfung von zwei unterschiedlichen C‐H‐Bindungen unter oxidativen Bedingungen ermöglichen. Diesen Methoden ist gemeinsam, dass die reaktiven Zwischenstufen durch Aktivierung der beiden C‐H‐Bindungen in situ gebildet werden. Diese Strategie wurde von der Gruppe von Li als dehydrierende Kreuzkupplung (CDC, “cross‐dehydrogenative coupling”) eingeführt und eröffnet abfallarme Synthesealternativen zu klassischen Kupplungsverfahren, die sich auf die Verwendung von vorfunktionalisierten Ausgangsstoffen stützen. Dieser Aufsatz hebt die Fortschritte auf dem Gebiet der dehydrierenden C sp 3‐C‐Bindungsknüpfungen hervor und liefert einen umfassenden Überblick über die vorhandenen Verfahren.

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Oxidative Arylation of Isochroman

Cited by 99 publications

References 58 publications

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

Dehydrierende Kreuzkupplungen von C‐H‐Bindungen: vielseitige Verfahren zur Bildung von C‐C‐Bindungen

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