Direct C‐2 Alkylation of Quinoline <i>N</i>‐Oxides with Ethers <i>via</i> Palladium‐Catalyzed Dehydrogenative Cross‐Coupling Reaction

Wu, Zhi‐Yong; Pi, Chao; Cui, Xiuling; Bai, Jie

doi:10.1002/adsc.201300111

Cited by 139 publications

(53 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…(1)]. [59] Substitution at the C2-position Scheme 22. Direct alkylationo fpyridines, quinolines, and their N-oxides with cycloalkanes or with aliphatic alcohols by a1,5-HAT strategy.…”

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

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.

show abstract

“…(1)]. [59] Substitution at the C2-position Scheme 22. Direct alkylationo fpyridines, quinolines, and their N-oxides with cycloalkanes or with aliphatic alcohols by a1,5-HAT strategy.…”

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

show abstract

“…For example, this transformation could be readily promoted using palladium(II) acetate as a catalyst and excess TBHP as a stoichiometric oxidant for the direct alkylation of quinoline and pyridine N ‐oxides to afford the corresponding alkylated N ‐oxides in good yields, as reported by Cui and Wu [Scheme , Eq. (1)] . Substitution at the C2‐position appears to be essential to avoid double alkylation.…”

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

View full text Add to dashboard Cite

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.

show abstract

“…Meanwhile, benzamide as the N-N bond decomposition product was also detected. [12] The optimized reaction conditions were identified as 0.2 mmol 1a in the presence of 0.3 equiv. resulted in 3aЈ becoming the major product ( Entry 11) provided only a marginal improvement, which did not justify the large excess.…”

Section: Resultsmentioning

confidence: 99%