Direct, Catalytic, and Regioselective Synthesis of 2-Alkyl-, Aryl-, and Alkenyl-Substituted <i>N</i>-Heterocycles from <i>N</i>-Oxides

Larionov, Oleg V.; Stephens, David E.; Mfuh, Adelphe; Chavez, Gabriel

doi:10.1021/ol403631k

Cited by 134 publications

(43 citation statements)

References 66 publications

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“…[46] Under these conditions,avariety of primary,secondary,and tertiary alkyl groups could be readily introduced with variable efficiencies and the authors later extended their procedure to the use of 2-trifluoroboratochromanones. [50] Another example is the development of ab ase-promoted metal-free procedure for the direct alkylation of N-heterocycle N-oxides with 1,1diborylalkanes (Scheme 20). (2)], [48] and for the direct alkylation of C2-substituted pyridine Noxides with potassium alkyltrifluoroborates by using Ru-(bpy) 3 (PF 6 ) 2 and BI-OAc [Scheme 19, Eq.…”

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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Section: Alkylation With Alkyl Halidesmentioning

confidence: 99%

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

2019

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“…For example, Grignard reagents together with copper catalysis were exploited by Larionov for the direct alkylation of various N ‐oxides to afford the desired alkylated N‐heterocycles in good yields. Noteworthy, the reaction is effective for the C2‐functionalization of some biologically relevant heterocycles . Another example is the development of a base‐promoted metal‐free procedure for the direct alkylation of N‐heterocycle N ‐oxides with 1,1‐diborylalkanes (Scheme ) .…”

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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“…[45] The reaction exhibits a broad scope for both heterocyclic N-oxides and various Grignard reagents. [45] The reaction exhibits a broad scope for both heterocyclic N-oxides and various Grignard reagents.…”

Section: Alkylation Of N-oxidesmentioning

confidence: 99%

Recent Advances in Catalytic Functionalization of N‐Oxide Compounds via CH Bond Activation

2014

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N-Oxide compounds are very important intermediates in synthetic organic chemistry as well as in the chemical industry. Numerous efforts have been devoted to the development of efficient approaches for the C À H bond activation and functionalization of N-oxides in recent years, including arylation, alkenylation, alkylation, acyloxylation, amination, amidation and sulfonylation. In this review, recent advances in this area are summarized and their mechanisms are discussed.

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Direct, Catalytic, and Regioselective Synthesis of 2-Alkyl-, Aryl-, and Alkenyl-Substituted N-Heterocycles from N-Oxides

Cited by 134 publications

References 66 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

Recent Advances in Catalytic Functionalization of N‐Oxide Compounds via CH Bond Activation

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