Accelerating Electrochemical Synthesis through Automated Flow: Efficient Synthesis of Chalcogenophosphites

Wirth, Thomas; Amri, Nasser

doi:10.1055/s-0040-1707141

Cited by 22 publications

(5 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on the experimental observation and literature precedents, a plausible mechanism for this electrochemical fluorination of P(O)–H motifs is proposed in Scheme . Initially, Cl – was electrooxidized to Cl • , followed by hydrogen atom abstraction (HAT), and phosphorus radical intermediate I was formed.…”

Section: Results and Discussionmentioning

confidence: 99%

Et₄NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Wang

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

An electrochemical synthetic strategy to construct P(O)−F bonds was developed via the Atherton−Todd reaction. Promoted by Et 4 NCl, a series of biologically active phosphoric fluorides were synthesized by use of commercially available P(O)−H feedstocks and Et 3 N•3HF as the F-source. With this protocol, some potentially functional P(O)−OR and P(O)−SR motifs could also be smoothly forged. This sustainable fluorination approach features step-economy, is chemicaloxidant-and metal-catalyst-free, and offers low cost and mild conditions. Additionally, cyclic voltammetry and control experiments were conducted to propose a reasonable mechanism. Article pubs.acs.org/joc

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Et₄NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Wang

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…This review demonstrated the efficacy of the electrosynthesis as an excellent, efficient and green way for constructing new bond such as CÀ P, OÀ P, NÀ P, SÀ P, and SeÀ P. Even with this progress, still the need to develop the catalyst-free bond process, especially for NÀ P and OÀ P bonds. Additionally, there has been made recent progress to access phosphorylated compounds using flow and automated technology [57] that would be an additional step for easy handling of chemicals and less involvement of human, allowing the chemists, at the same time, to apply their expertise to other pressing challenges in their fields.…”

Section: Discussionmentioning

confidence: 99%

“…In the same year, the group of Wirth [57] demonstrated that automated flow electrochemical reactor was successfully useful for the synthesis of organoselenophosphorus (scheme 39). With diphenyl diselenide and phosphites derivatives a large scope of desired compounds was formed in moderate to good yields.…”

Section: Sà P Bond Formationmentioning

confidence: 99%

Electrochemical Phosphorylation of Organic Molecules

Sbei

Martins

Shirinfar

et al. 2020

The Chemical Record

View full text Add to dashboard Cite

Organophosphorus chemistry is a broad field with multi-dimensional applications in research area of organic, biology, drug design and agrochemicals. Conventional methods have been adopted extensively to access phosphorylated compounds that rely on the use of toxic, moisture sensitive phosphorylating agents and occur in the presence of oxidants, catalysts, as well as high temperatures and harsh conditions are required for complete transformations. However, recent progress has been made for phosphorylation reactions using electricity to introduce green and sustainable synthetic procedures. These reactions can be performed at mild conditions and proceed with excellent atom economy. Herein, we targeted electrochemical phosphorylation reactions with generation of new bonds such as C(sp 3) À P, C(sp 2) À P, OÀ P, NÀ P, SÀ P and SeÀ P. This review is aimed to offer an overview of recent developments in the synthetic methodology to easy access of organophosphorus compounds using electrochemistry.

show abstract

“…Much effort has been committed to exploring synthetic methods for the construction of P–Se/P–S bonds over the past few decades. The existing methods for constructing P–Se/P–S bonds are often related to transition metal catalysis, strong oxidants, base catalysis, photocatalysis, electrochemical methods, etc. ,, However, some of the existing methods have the disadvantages of being a multistep reaction, using toxic reagents, requiring harsh reaction conditions, requiring long reaction times, having low functional group tolerance, etc. For example, in 2016, an efficient Pd catalyst dehydrogenative coupling method for constructing a P–S bond with good yields was reported .…”

Section: Introductionmentioning

confidence: 99%

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air

Zhang,

Guo,

Zhao

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

The NaOAc-assisted aerobic oxidation reaction of pentacoordinate hydrospirophosphoranes and dichalcogenyl compounds with open air as a green oxidant has been developed under mild conditions. A series of novel pentacoordinate spirophosphoranes with P–Se/P–S bonds were synthesized in excellent yields. The reaction mechanism was determined by 31P nuclear magnetic resonance tracing experiments, high-resolution mass spectrometry tracing experiments, and X-ray diffraction analysis. The method features a broad substrate scope, good functional group tolerance, and a high degree of atomic utilization and is meaningful for the synthesis of bioactive chalcogenphosphate compounds with chalcogen and phosphorus moieties.

show abstract

Accelerating Electrochemical Synthesis through Automated Flow: Efficient Synthesis of Chalcogenophosphites

Cited by 22 publications

References 8 publications

Et₄NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Et₄NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Electrochemical Phosphorylation of Organic Molecules

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air

Contact Info

Product

Resources

About

Accelerating Electrochemical Synthesis through Automated Flow: Efficient Synthesis of Chalcogenophosphites

Cited by 22 publications

References 8 publications

Et4NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Et4NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Electrochemical Phosphorylation of Organic Molecules

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air

Contact Info

Product

Resources

About

Et₄NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds

Et₄NCl-Promoted Electrochemical Atherton-Todd Type Reaction to Construct P(O)–F Bonds