Catalyst-controlled stereoselective carbon–heteroatom bond formations by N-heterocyclic carbene (NHC) organocatalysis

Wang, Yanyan; Liu, Yonggui; Zhang, Sha; Long, Yijie; Wu, Xingxing

doi:10.1039/d3qo00667k

Cited by 6 publications

(2 citation statements)

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“…2, all the organic catalysts that have been described in this review are summarized. From a mechanistic viewpoint, secondary amines, 6 phosphines, 7 and N-heterocyclic carbenes 8 are termed covalent catalysts because of the formation of a covalent bond between the catalyst and substrate. Brønsted acid catalysts 9 rely on hydrogen-bonding interactions between the catalyst and substrate, and can be regarded as representative non-covalent catalysts.…”

Section: Introductionmentioning

confidence: 99%

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Li,

Yao

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Li,

Yao

et al. 2024

Org. Chem. Front.

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“…In recent decades, many new and efficient synthetic methods such as photocatalysis, 2 electrocatalysis, 3 organocatalysis, 4 transition metal catalysis, 5 C−H activation, 6 cycloaddition, 7 and solvent-free technology 8 have been developed extensively to construct various heterocycles. Furthermore, synthesis of heterocycles from different kinds of starting materials has also been reviewed.…”

Section: Introductionmentioning

confidence: 99%

Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect

Zheng,

Li,

et al. 2024

Org. Process Res. Dev.

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Oxygen-, nitrogen-, and sulfur-containing heterocycles exhibit remarkable biological and pharmaceutical activities that are often found in naturally occurring products, pharmaceutical molecules, and synthetic compounds. Therefore, the synthesis of heterocycle building blocks has gained huge attention in the past decade. Compared with the modification of heterocyclic compounds, the construction of heterocyclic compounds from scratch is more attractive. In this Perspective, we describe our recent advances in the rational design and strategic application of the de novo synthesis of various synthetically and biologically important heterocycles. The organization of the Perspective is categorized in the following order: (a) type of heterocycle, (b) ring size of heterocycle, (c) number of heteroatoms, and (d) fused heterocycles. Moreover, some significant and representative synthetic methodologies and their synthetic applications and brief reaction mechanisms have also been described. We hope that this Perspective will help to provide a guideline for researchers who are interested in this fertile area.

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N‐Heterocyclic Carbene Enabled Functionalization of Inert C(Sp³)−H Bonds via Hydrogen Atom Transfer (HAT) Processes

Lu,

Su,

Pan

et al. 2024

Chemistry A European J

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Developing methods to directly transform C(sp3)‐H bonds is crucial in synthetic chemistry due to their prevalence in various organic compounds. While conventional protocols have largely relied on transition metal catalysis, recent advancements in organocatalysis, particularly with radical NHC catalysis have sparked interest in the direct functionalization of "inert" C(sp3)‐H bonds for cross C‐C coupling with carbonyl moieties. This strategy involves selective cleavage of C(sp3)‐H bonds to generate key carbon radicals, often achieved via hydrogen atom transfer (HAT) processes. By leveraging the bond dissociation energy (BDE) and polarity effects, HAT enables the rapid functionalization of diverse C(sp3)‐H substrates, such as ethers, amines, and alkanes. This mini‐review summarizes the progress in carbene organocatalytic functionalization of inert C(sp3)‐H bonds enabled by HAT processes, categorizing them into two sections: 1) C‐H functionalization involving acyl azolium intermediates; and 2) functionalization of C‐H bonds via reductive Breslow intermediates.

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Catalyst-controlled stereoselective carbon–heteroatom bond formations by N-heterocyclic carbene (NHC) organocatalysis

Abstract: The development of synthetic strategies towards enantioselective access to carbon-heteroatom bonds by means of catalyst control continues to receive considerable interests in organic chemistry. Over the past decades, N-heterocyclic carbene...

Cited by 6 publications

References 144 publications

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect

N‐Heterocyclic Carbene Enabled Functionalization of Inert C(Sp³)−H Bonds via Hydrogen Atom Transfer (HAT) Processes

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Catalyst-controlled stereoselective carbon–heteroatom bond formations by N-heterocyclic carbene (NHC) organocatalysis

Abstract: The development of synthetic strategies towards enantioselective access to carbon-heteroatom bonds by means of catalyst control continues to receive considerable interests in organic chemistry. Over the past decades, N-heterocyclic carbene...

Cited by 6 publications

References 144 publications

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect

N‐Heterocyclic Carbene Enabled Functionalization of Inert C(Sp3)−H Bonds via Hydrogen Atom Transfer (HAT) Processes

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N‐Heterocyclic Carbene Enabled Functionalization of Inert C(Sp³)−H Bonds via Hydrogen Atom Transfer (HAT) Processes