Ruthenium-Catalyzed Selectively Oxidative C–H Alkenylation of <i>N</i>-Acylated Aryl Sulfonamides by Using Molecular Oxygen as an Oxidant

Li, Xueyuan; Hu, Xiao; Liu, Zijie; Yang, Jingshu; Mei, Bo; Dong, Yunhui; Liu, Gang

doi:10.1021/acs.joc.0c00242

Cited by 22 publications

(9 citation statements)

References 44 publications

(17 reference statements)

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“…An alternative mechanistic pathway would be the generation of hydrazide first from 5 - 38 and water, which in turn attacks aryne to give 5-37 . Moreover, these N-arylation protocols have become general methods with many synthetic applications. − …”

Section: Nucleophilic Addition Reactionsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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Section: Nucleophilic Addition Reactionsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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“…Liu group [64] again significantly demonstrated sulphonamide directed ortho alkenylation/annulation reaction utilizing different conditions (entry 4, Table 1). They employed ruthenium as a catalyst with the advantage of low toxicity.…”

Section: The C−c and C−n Bond Formation/annulations Reactionmentioning

confidence: 95%

The Role of Sulphonamides and N‐Sulphonyl Ketimines/Aldimines as Directing Groups in the Field of C−H Activation

Galla

Bora

Shankaraiah

2021

Chemistry An Asian Journal

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Sulphonamides and N‐sulphonyl ketimines/aldimines have turned out to be versatile motifs in the field of synthetic and medicinal chemistry. The field of C−H activation/functionalization flourished remarkably due to their synthetic applicability and directing group plays a remarkable role to achieve regioselectivity in these reactions. The current review summarizes recent tactics by utilizing sulphonamides and N‐sulphonyl ketimines/aldimines as directing groups for C−H activation or functionalization. As a directing group, they also facilitate site selectivity and late‐stage functionalization of drug molecules in order to construct complex scaffolds of therapeutic importance by C−H activation.

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“…For example, Ru( p -cymene) complexes can use oxygen as a sole oxidant for C–H activation, alkyne annulation and selective oxidative C–H alkenylation in an anhydrous solvent. 9 These homogeneous complexes have excellent atom economy, and provide a potential method for the catalytic oxidation of formaldehyde under anhydrous conditions. This is different from the catalytic oxidation by nanocatalysts involving water.…”

Section: Introductionmentioning

confidence: 99%