Tunable Single and Double γ‐C−H Arylation of Phenylacetamides Directed by <i>o</i>‐Aminophenols

Tu, Zhi; Du, Yi; Cao, Xiaoji; Liu, Yunyun

doi:10.1002/adsc.201900866

Cited by 12 publications

(4 citation statements)

References 36 publications

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“…In addition, OAP was also recently found to be applicable as a DG precursor for similar selective syntheses of arylated phenylacetamides with expanded product diversity, but stepwise amidation and C-H arylation was required. 24 Scheme 4 AQ-directed aryl C-H arylation of phenylacetamides via in situ amidation; Q = aminoquinoline…”

Section: Special Topic Synthesismentioning

confidence: 99%

Step-Economical C–H Activation Reactions Directed by In Situ Amidation

Zhao

Liu

2020

Synthesis

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Owing to the inherent ability of amides to chelate transition-metal catalysts, amide-directed C–H activation reactions constitute a major tactic in directed C–H activation reactions. While the conventional procedures for these reactions usually involve prior preparation and purification of amide substrates before the C–H activation, the step economy is actually undermined by the operation of installing the directing group (DG) and related substrate purification. In this context, directed C–H activation via in situ amidation of the crude material provides a new protocol that can significantly enhance the step economy of amide-directed C–H activation. In this short review, the advances in C–H bond activation reactions mediated or initiated by in situ amidation are summarized and analyzed.1 Introduction2 In Situ Amidation in Aryl C–H Bond Activation3 In Situ Amidation in Alkyl C–H Bond Activation4 Annulation Reactions via Amidation-Mediated C–H Activation5 Remote C–H Activation Mediated by Amidation6 Conclusion

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Section: Special Topic Synthesismentioning

confidence: 99%

Step-Economical C–H Activation Reactions Directed by In Situ Amidation

Zhao

Liu

2020

Synthesis

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“…2A, ii ). Similarly, Liu and co-workers in 2019 executed tuneable mono- and di- ortho- C–H arylation of phenylacetamides 29 enabled by o -aminophenol as the directing auxiliary. The absence of the hydroxyl group was detrimental for this ortho- C–H arylation (Fig.…”

Section: Introductionmentioning

confidence: 99%

Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation

et al. 2022

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Biaryl scaffolds are found in natural products and drug molecules and exhibit a wide range of biological activities. In past decade, the transition metal-catalyzed C–H arylation reaction came out as an effective tool for the construction of biaryl motifs. However, traditional transition metal-catalyzed C–H arylation reactions have limitations like harsh reaction conditions, narrow substrate scope, use of additives etc. and therefore encouraged synthetic chemists to look for alternate greener approaches. This review aims to draw a general overview on C–H bond arylation reactions for the formation of C–C bonds with the aid of different methodologies, majorly highlighting on greener and sustainable approaches.

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“…Adjustment of reaction time and temperature or the concentration of substrates may have no pronounced effect on the proportions of mono- or diarylated compounds that are produced. Different strategies have been developed to achieve high selectivity − of mono- or diarylation. These include use of different directing groups − and modification of the substrates, , the leaving groups, , the proportions of the coupling partner, the metal species or the additives. − …”

Section: Introductionmentioning

confidence: 99%

“…Different strategies have been developed to achieve high selectivity − of mono- or diarylation. These include use of different directing groups − and modification of the substrates, , the leaving groups, , the proportions of the coupling partner, the metal species or the additives. − …”

Section: Introductionmentioning

confidence: 99%

MIA-Directed 2-Pyridione-Enabled Selective Ortho-C–H Arylation of Phenylalanine: A Mechanistic Study

et al. 2021

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The 2-methoxyiminoacyl-mediated arylation of substituted phenylalanines has been examined. Selective monoarylation at the ortho position was achieved using pyridone ligands which decelerate the arylation process. Density functional theory (DFT) study of a continuous C−H arylation process that included the first and second arylation stage was performed. The computational result shows that the introduction of a pyridone ligand obviously disfavors the second arylation stage, which directly contributes to the selectivity between the mono/diarylated products. Furthermore, results of the kinetic isotope effect and a control experiment are agreed with DFT study.

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Tunable Single and Double γ‐C−H Arylation of Phenylacetamides Directed by o‐Aminophenols

Cited by 12 publications

References 36 publications

Step-Economical C–H Activation Reactions Directed by In Situ Amidation

Step-Economical C–H Activation Reactions Directed by In Situ Amidation

Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation

MIA-Directed 2-Pyridione-Enabled Selective Ortho-C–H Arylation of Phenylalanine: A Mechanistic Study

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