Radical CH Alkylation of BODIPY Dyes Using Potassium Trifluoroborates or Boronic Acids

Verbelen, Bram; Rezende, Lucas Cunha Dias de; Boodts, Stijn; Jacobs, Jeroen; Meervelt, Luc Van; Hofkens, Johan; Dehaen, Wim

doi:10.1002/chem.201500938

Cited by 60 publications

(29 citation statements)

References 75 publications

(34 reference statements)

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“…Similar strategies have also been reported for the prenylation of various azines, as well as of some azoles, by using a tandem Minisci‐type alkylation/dehydration sequence from potassium alkyltrifluoroborates and for the direct functionalization of BODIPY dyes using primary, secondary, and tertiary alkyl‐, as well as aryl‐ and alkenyltrifluoroborates or boronic acids . Both processes rely on the use of Mn(OAc) 3 ⋅2 H 2 O as a stoichiometric oxidant.…”

Section: Alkylation Of Heteroarenesmentioning

confidence: 84%

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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Section: Alkylation Of Heteroarenesmentioning

confidence: 84%

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

Evano

Theunissen

2019

Angew Chem Int Ed

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“…[40] Similar strategies have also been reported for the prenylation of various azines,a sw ell as of some azoles,b y using atandem Minisci-type alkylation/dehydrationsequence from potassium alkyltrifluoroborates [41] and for the direct functionalization of BODIPY dyes using primary,secondary, and tertiary alkyl-, as well as aryl-and alkenyltrifluoroborates or boronic acids. [42] Both processes rely on the use of Mn(OAc) 3 ·2 H 2 Oa sastoichiometric oxidant. More recently, molecular oxygen was also shown by Liu to be sufficient to smoothly promote the direct alkylation of lepidine and other related azines,a sw ell as of some azoles,w ith primary and secondary alkylboronic acids (Scheme 17).…”

Section: Alkylation With Alkyl Halidesmentioning

confidence: 99%

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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“…[40] ¾hnliche Strategien wurden auch fürd ie Prenylierung verschiedener Azine sowie einiger Azole berichtet, die über eine Sequenz aus Minisci-Alkylierung und Dehydrierung aus Kaliumalkyltrifluorboraten durchgeführt wurde, [41] und für die direkte Funktionalisierung von BODIPY-Farbstoffen mit primären, sekundären und tertiären Alkyl-ebenso wie Arylund Alkenyltrifluorboraten oder -boronsäuren. [42] Beide Verfahren beruhen auf der Verwendung von Mn-(OAc) 3 ·2 H 2 Oa ls stçchiometrisch eingesetztes Oxidationsmittel. Vork urzem wurde von Liu gezeigt, dass auch molekularer Sauerstoff eine direkte Alkylierung von Lepidin und anderen verwandten Azinen sowie einigen Azolen mit primären und sekundären Alkylboronsäuren fçrdern kann (Schema 17).…”

Section: Alkylierung Mit Alkylmetallreagenzienunclassified

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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Radical CH Alkylation of BODIPY Dyes Using Potassium Trifluoroborates or Boronic Acids

Cited by 60 publications

References 75 publications

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

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

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

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

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