Benzenediazonium Tetrafluoroborate

Maas, Gerhard; Tanaka, M.; Sakakura, Toshiyasu

doi:10.1002/047084289x.rb009

Cited by 4 publications

(1 citation statement)

References 112 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sakakura reported that some diazonium salts such as 3-methoxybenzenediazonium ( 2m ) and certain heteroarenediazonium tetrafluoroborates are known to decompose when dried, which may explain the observed low yield obtained for biaryl 3m (13%). Indeed, Heinrich and co-workers also reported problems with the use of an aryldiazonium chloride containing the meta -methoxy group, which partially decomposed before the addition to the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

et al. 2019

View full text Add to dashboard Cite

A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96%. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the ortho, meta, or para positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.

show abstract

Section: Resultsmentioning

confidence: 99%

Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

et al. 2019

View full text Add to dashboard Cite

show abstract

A Heck–Matsuda Process for the Synthesis of β‐Arylethenesulfonyl Fluorides: Selectively Addressable Bis‐electrophiles for SuFEx Click Chemistry

et al. 2016

View full text Add to dashboard Cite

AH eck-Matsuda process for the synthesis of the otherwise difficult to access compounds, b-arylethenesulfonyl fluorides,i sd escribed. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride,o rE SF) undergoes b-arylation with stable and readily prepared arenediazonium tetrafluoroborates in the presence of the catalyst palladium(II) acetate to affordt he Eisomer sulfonyl analogues of cinnamoyl fluoride in 43-97 % yield. The b-arylethenesulfonyl fluorides are found to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) clickc hemistry,inwhich either the alkenyl moiety or the sulfonyl fluoride group can be the exclusive site of nucleophilic attack under defined conditions,m aking these rather simple cores attractive for covalent drug discovery.

show abstract

A Heck–Matsuda Process for the Synthesis of β‐Arylethenesulfonyl Fluorides: Selectively Addressable Bis‐electrophiles for SuFEx Click Chemistry

et al. 2016

View full text Add to dashboard Cite

A Heck-Matsuda process for the synthesis of the otherwise difficult to access compounds, β-arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride, or ESF) undergoes β-arylation with stable and readily prepared arenediazonium tetrafluoroborates in the presence of the catalyst palladium(II) acetate to afford the E-isomer sulfonyl analogues of cinnamoyl fluoride in 43–97% yield. The β-arylethenesulfonyl fluorides are found to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) click chemistry, in which either the alkenyl moiety or the sulfonyl fluoride group can be the exclusive site of nucleophilic attack under defined conditions, making these rather simple cores attractive for covalent drug discovery.

show abstract

Benzenediazonium Tetrafluoroborate

Cited by 4 publications

References 112 publications

Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

A Heck–Matsuda Process for the Synthesis of β‐Arylethenesulfonyl Fluorides: Selectively Addressable Bis‐electrophiles for SuFEx Click Chemistry

A Heck–Matsuda Process for the Synthesis of β‐Arylethenesulfonyl Fluorides: Selectively Addressable Bis‐electrophiles for SuFEx Click Chemistry

Contact Info

Product

Resources

About