Metal‐free Nucleophilic α‐Azidation of α‐Halohydroxamates with Azidotrimethylsilane

Lee, Chang Yoon; Kim, Sung‐Gon

doi:10.1002/ajoc.202100556

Cited by 6 publications

(3 citation statements)

References 47 publications

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“…Importantly, group synthesized biologically important triazole scaffold via CuAAC reaction of dialkyl α-azido carbonyls (Scheme 40). [56] Saha and group in 2022 reported a method to synthesize 3,3'-disubstituted peroxyoxindole which is ubiquitously found in many biologically active compounds and natural products. They were able to synthesize molecule 136 by employing azaoxyallyl cation under transition metal-free condition.…”

Section: Aza-oxyallyl Cations As An Alkylating Agentmentioning

confidence: 99%

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Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Deeksha

Singh

2022

Eur J Org Chem

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Aza‐oxyallyl cations, as proposed by Sheehan in the 1960s have garnered significant attention among the synthetic organic community, owing to their diverse reactivity profile for constructing N‐scaffolds of biological interest. During its initial growth, aza‐oxyallyl cations were used effectively as a 3‐unit synthon as 1,3 dipoles to create N‐heterocycles via cycloaddition reactions, wherein aza‐oxyallyl cation served as electrophilic counterpart. Recently, new variations of aza‐oxyallyl cations reactivity have been reported, including its usage as a 1,4 dipole in cycloaddition reactions, domino reactions, and the unique alkylating ability of heteroatoms. This review article provides an update of the recent developments in this area and the prevailing mechanistic insight.

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Section: Aza-oxyallyl Cations As An Alkylating Agentmentioning

confidence: 99%

“…Importantly, group synthesized biologically important triazole scaffold via CuAAC reaction of dialkyl α‐azido carbonyls (Scheme 40). [56] …”

Section: Aza‐oxyallyl Cations As An Alkylating Agentmentioning

confidence: 99%

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Deeksha

Singh

2022

Eur J Org Chem

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“…In fact, due to the high affinity of fluoride for silicon that leads to the formation of pentacoordinate complexes, the use of fluoride-based catalysts is usually exploited to generate the azido ion from TMSN 3 . , Under these conditions, the formation of hydrazoic acid is avoided, minimizing the risk associated with the process . Moreover, in the context of a sustainable chemical production, heterogeneous systems, featuring F – ion on solid supports, were also proposed to promote the catalyst recovery and reuse. − …”

Section: Introductionmentioning

confidence: 99%

POLITAG-M-F as Heterogeneous Organocatalyst for the Waste-Minimized Synthesis of β-Azido Carbonyl Compounds in Batch and under Flow Conditions

Valentini

Brufani

Rossini

et al. 2023

ACS Sustainable Chem. Eng.

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We herein report a waste minimization protocol for the β-azidation of α,β-unsaturated carbonyl compounds using TMSN3. The selection of the appropriate catalyst (POLITAG-M-F), in combination with the reaction medium, resulted in enhanced catalytic efficiency and a low environmental footprint. The thermal and mechanical stability of the polymeric support allowed us to recover the POLITAG-M-F catalyst for up to 10 consecutive runs. The CH3CN:H2O azeotrope has a 2-fold positive effect on the process, increasing the efficiency of the protocol and minimizing waste generation. Indeed, the azeotropic mixture, used as a reaction medium and for the workup procedure, was recovered by distillation, leading to an easy and environmentally friendly procedure for product isolation in high yield and with a low E-factor. A comprehensive evaluation of the environmental profile was performed by the calculation of different green metrics (AE, RME, MRP, 1/SF) and a comparison with other literature available protocols. A flow protocol was defined to scale-up the process, and up to 65 mmol of substrates were efficiently converted with a productivity of 0.3 mmol/min.

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[8+3]‐Cycloaddition Reactions of Heptafulvenes or Azaheptafulvenes with α‐Halohydroxamates

Xie

et al. 2022

Asian J Org Chem

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The base-mediated higher-order [8 + 3]-cycloaddition reactions of heptafulvenes or azaheptafulvenes with αhalohydroxamates have been achieved under mild and metal-free conditions. These reactions do not only provide a direct route for the synthesis of highly functionalized cyclo-heptatriene-fused piperidinones and piperazinones in moderate to excellent yields, but they also enrich the chemistry of heptafulvenes and azaheptafulvenes. Furthermore, gramscale reactions and further derivatizations demonstrated the synthetic potential of these cycloaddition reactions.

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Metal‐free Nucleophilic α‐Azidation of α‐Halohydroxamates with Azidotrimethylsilane

Cited by 6 publications

References 47 publications

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

POLITAG-M-F as Heterogeneous Organocatalyst for the Waste-Minimized Synthesis of β-Azido Carbonyl Compounds in Batch and under Flow Conditions

[8+3]‐Cycloaddition Reactions of Heptafulvenes or Azaheptafulvenes with α‐Halohydroxamates

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