Palladium‐Catalyzed Direct Cyclopropylation of Heterocycles

Wu, Xiangqian; Lei, Chuanhu; Yue, Guizhou; Zhou, Jianrong

doi:10.1002/anie.201504735

Cited by 38 publications

(20 citation statements)

References 120 publications

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“…[122] As previously discussed in Section 2.1.2, Zhou reported ageneral and broadly applicable palladium-catalyzed alkylation of heteroarenes using secondary and tertiary alkyl halides. [123] Interestingly,t he relative configuration of the cyclopropane ring was retained in the desired products,a nd cyclopropyl radicals were not involved in the productive mechanistic pathway. Ayear later,this procedure was extended to the direct cyclopropanation of azoles with cyclopropyl iodides.…”

Section: Angewandte Chemiementioning

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: Angewandte Chemiementioning

confidence: 99%

“…Ayear later,this procedure was extended to the direct cyclopropanation of azoles with cyclopropyl iodides. [123] Interestingly,t he relative configuration of the cyclopropane ring was retained in the desired products,a nd cyclopropyl radicals were not involved in the productive mechanistic pathway.…”

Section: Angewandte Chemiementioning

confidence: 99%

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

2019

View full text Add to dashboard Cite

show abstract

“…In addition to electron‐deficient heteroarenes, this procedure was also amenable to the alkylation of various azoles with a wide range of alkyl iodides and bromides, the desired alkylated products being formed in excellent yields (Scheme ). A year later, this procedure was extended to the direct cyclopropanation of azoles with cyclopropyl iodides . Interestingly, the relative configuration of the cyclopropane ring was retained in the desired products, and cyclopropyl radicals were not involved in the productive mechanistic pathway.…”

Section: Alkylation Of Heteroarenesmentioning

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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“…Ein Jahr später wurde dieses Verfahren auf die direkte Cyclopropanierung von Azolen mit Cyclopropyliodiden erweitert. [123] Interessanterweise blieb die relative Konfiguration des Cyclopropans in den gewünschten Produkten erhalten, und es waren keine Cyclopropylradikale an der Produktbildung beteiligt.…”

Section: Angewandte Chemieunclassified

Jenseits von Friedel und Crafts: dirigierte Alkylierung von C‐H‐Bindungen in Arenen

Evano

Theunissen

2019

Angewandte Chemie

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Die Alkylierung von Arenen ist eine der grundlegendsten Transformationen in der chemischen Synthese und führt in vielen wissenschaftlichen Bereichen zu privilegierten Molekülgerüsten. Klassische Methoden für die Einführung von Alkylgruppen in Arene beruhen zumeist auf der Friedel‐Crafts‐Reaktion, Radikaladditionen, Metallierungen oder Präfunktionalisierungen von Arenen; die Anwendungsbreite, Effizienz und Selektivität dieser Methoden sind jedoch begrenzt. Außerdem bauen sie auf der inhärenten Reaktivität des Ausgangsarens auf, die die Alkylierung in einer bestimmten Position bevorzugt und die Einführung von Alkylketten an anderen Stellen wesentlich schwieriger macht. Dieses Problem kann durch die Verwendung einer dirigierenden Gruppe angegangen werden, die in Gegenwart eines Metallkatalysators die regioselektive Alkylierung einer C‐H‐Bindung vereinfacht. Diese dirigierten Alkylierungen von C‐H‐Bindungen in Arenen werden im vorliegenden Aufsatz zusammengefasst.

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Palladium‐Catalyzed Direct Cyclopropylation of Heterocycles

Cited by 38 publications

References 120 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

Jenseits von Friedel und Crafts: dirigierte Alkylierung von C‐H‐Bindungen in Arenen

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