Synthesis, crystal structure, catalytic dimerization and S H insertion of new porphyrin diazoketones

Carrié, Daniel; Roisnel, Thierry; Simonneaux, Gérard

doi:10.1016/j.molstruc.2018.03.108

Cited by 8 publications

(2 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…High substrate reactivity helped avoid diazomethane accumulation, making ethyl chloroformate an optimal and safe activator for “dry” CH 2 N 2 protocols. Only a few examples of molecular structures of diazoketones − or their derivatives , are available in the literature. Therefore, we studied diazoketones 2a – e by using a single crystal X-ray diffraction method.…”

Section: Resultsmentioning

confidence: 99%

Practical Synthetic Method for Amino Acid-Derived Diazoketones Shelf-Stable Reagents for Organic Synthesis

Pendiukh,

Yakovleva,

Stadniy

et al. 2023

Org. Process Res. Dev.

View full text Add to dashboard Cite

A novel approach for safe generation of diazomethane-contained organic solution was proposed using a serial flow reactor. The productivity of diazomethane generation reached 0.45 mol/h. Several chiral diazoketones have been prepared in quantities up to 150 g through the reaction of diazomethane with mixed anhydrides, generated in situ by the treatment of Bocprotected α-amino acids with ethyl chloroformate. The synthesized diazoketones are crystalline substances stable up to 110−142 °C and can easily be purified on silica gel and stored for a long term. The overall stability and availability on a large scale allow considering such diazoketones as promising bench-stable reagents for a broad scope of applications. The quantum chemical studies show that the stability of diazoketones is connected with conjugation of the carbonyl group with the diazo moiety. As an example of applicability, the reaction of diazoketones with concentrated HBr gives the corresponding pure chiral α-bromoketones without additional purification.

show abstract

Section: Resultsmentioning

confidence: 99%

Practical Synthetic Method for Amino Acid-Derived Diazoketones Shelf-Stable Reagents for Organic Synthesis

Pendiukh,

Yakovleva,

Stadniy

et al. 2023

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…37 High substrate reactivity helped to avoid diazomethane accumulation, which made ethyl chloroformate an overall optimal and safe activator for "dry" CH2N2 protocols. Only a few examples of molecular structures of diazoketones [38][39][40][41][42][43] or their derivatives 44,45 are available in the literature, therefore we studied diazoketones 2a-e using a single crystal X-ray diffraction method.…”

Section: Synthesis Of Diazoketonesmentioning

confidence: 99%

Practical synthetic method for amino acids derived diazo-ketones – shelf-stable reagents for organic synthesis.

Pendiukh

Yakovleva

Stadniy

et al. 2023

Preprint

View full text Add to dashboard Cite

A novel approach for a safe generation of the diazomethane-contained organic solution has been proposed using a serial flow reactor. The productivity of the diazomethane generation has reached 0.45 mol/h. Several chiral diazoketones have been prepared in quantities up to 150 g through the reaction of diazomethane with mixed anhydrides, generated in situ by treatment of Boc-protected α-amino-acids with ethyl chloroformate. The synthesized diazoketones are crystalline sub-stances stable up to 110-142 °C and can easily be purified on silica gel and stored for a long term. The overall stability and availability on a large scale allow considering such diazoketones as promising bench-stable regents for the broad scope of applications. The quantum chemical studies show that the stability of diazoketones is probably connected with conjugation of the carbonyl group with diazo moiety. As an example of applicability: the reaction of diazoketones with concentrated HBr gives corresponding pure chiral α-bromoketones without additional purification was demonstrated.

show abstract

Reaction chemistry of noble metal porphyrins in solutions as a foundation for practical applications

Tyulyaeva

2020

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Synthesis, crystal structure, catalytic dimerization and S H insertion of new porphyrin diazoketones

Cited by 8 publications

References 23 publications

Practical Synthetic Method for Amino Acid-Derived Diazoketones Shelf-Stable Reagents for Organic Synthesis

Practical Synthetic Method for Amino Acid-Derived Diazoketones Shelf-Stable Reagents for Organic Synthesis

Practical synthetic method for amino acids derived diazo-ketones – shelf-stable reagents for organic synthesis.

Reaction chemistry of noble metal porphyrins in solutions as a foundation for practical applications

Contact Info

Product

Resources

About