Design of (β-diazo-α,α-difluoroethyl)phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids

Literature Information

Publication Date 2021-01-04
DOI 10.1039/D0QO01394C
Impact Factor 5.281
Authors

Haibo Mei, Jiang Liu, Romana Pajkert, Li Wang, Gerd-Volker Röschenthaler, Jianlin Han


View Original

Abstract

We elaborate a method for the generation of (2-diazo-1,1-difluoroethyl)phosphonates from (β-amino-α,α-difluoroethyl)phosphonates as precursors and their application as masked carbenes in coupling reactions with sulfonic acids under photochemical conditions. Varieties of coupling partners including aminophosphonates and sulfonic acids are well tolerated in this reaction affording unknown sulfonate esters in good yields. The strategy of this new diazo compound provides a valuable vista for the construction of functionalized difluoromethylene phosphonates and transformations of fluoro diazo compounds.

Related Literature

Hyperbranched PEG-based supramolecular nanoparticles for acid-responsive targeted drug delivery

Xiaofei Chen, Xuemei Yao, Chunran Wang, Li Chen, Xuesi Chen

2015-05-13 Paper

DOI: 10.1039/C5BM00061K

Recent progress in self-supported two-dimensional transition metal oxides and (oxy)hydroxides as oxygen evolution reaction catalysts

Jie Zhang, Conghui Si, Tianyi Kou, Jianfeng Wang, Zhonghua Zhang

2020-03-23 Review Article

DOI: 10.1039/C9SE01312A

A fluorescence nanoprobe for detecting the effect of different oxygen and nutrient conditions on breast cancer cells’ migration and invasion

Ping Zhou, Bo Liu, Mingming Luan, Na Li, Bo Tang

2021-05-25 Communication

DOI: 10.1039/D1BM00619C

Mesoscopic analyses of the impact of morphology and operating conditions on the transport resistances in a proton-exchange-membrane fuel-cell catalyst layer

Yu-Tong Mu, Adam Z. Weber, Zhao-Lin Gu, Tobias Schuler, Wen-Quan Tao

2020-05-01 Paper

DOI: 10.1039/D0SE00560F

Influence of high-pressure torsion deformation on the corrosion behaviour of a bioresorbable Mg-based alloy studied by positron annihilation

Philipp Brunner, Florian Brumbauer, Eva-Maria Steyskal, Oliver Renk, Annelie-Martina Weinberg, Hartmuth Schroettner, Roland Würschum

2021-04-30 Paper

DOI: 10.1039/D1BM00166C

Transforming waste cigarette filters into 3D carbon scaffolds for form-stable and energy conversion phase change materials

Malik Muhammad Umair, Yuang Zhang, Shufen Zhang, Xin Jin

2020-06-17 Paper

DOI: 10.1039/D0SE00368A

Highly basic solid catalysts obtained by spray drying of a NaAlO2 and boehmite suspension for the upgrading of glycerol to acetins

Sreerangappa Ramesh, Makhlouf Amoura, Damien P. Debecker

2020-05-04 Paper

DOI: 10.1039/D0SE00211A

Encapsulated Sb and Sb2O3 particles in waste-tire derived carbon as stable composite anodes for sodium-ion batteries

Manikandan Palanisamy, Vilas G. Pol, Kia Jackson, Charl J. Jafta, Craig A. Bridges, Sheng Dai, Alan M. Levine, Richard J. Lee

2020-05-04 Paper

DOI: 10.1039/D0SE00408A

Quantitative UPLC-MS/MS analysis of the gut microbial co-metabolites phenylacetylglutamine, 4-cresyl sulphate and hippurate in human urine: INTERMAP Study

Philip A. Clarke, Magda Bictash, Ian J. Brown, Mark Fidock, Thomas Ryckmans, Queenie Chan, Jeremiah Stamler

2011-10-19 Paper

DOI: 10.1039/C1AY05427A

Amino-functionalized MOF derived porous Fe3O4/N-doped C encapsulated within a graphene network by self-assembling for enhanced Li-ion storage

Weijuan Wang, Daming Chen, Hui Xu, Genxi Yu, Shangqi Sun, Wei Zhang, Jian Chen

2020-04-30 Paper

DOI: 10.1039/D0SE00112K

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.