Details

Autor(en) / Beteiligte

• Grigolato, Lucas
• Brittain, William D.G.
• Hudson, Alex S.
• Czyzewska, Maria M.
• Cobb, Steven L.

Titel

Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids

Ist Teil von

• Journal of fluorine chemistry, 2018-08, Vol.212, p.166-170

Ort / Verlag

United States: Elsevier B.V

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Herein, a series of aromatic pentafluorosulfanyl (SF5) containing amino acids are reported. A Negishi cross-coupling strategy utilising a catalyst system of Pd(dba)2 and SPhos afforded the aforementioned SF5 amino acids in yields between 35% and 42%. Two dipeptides utilising both the amine and carboxylic functionalities of the synthesised SF5 containing amino acids were prepared, demonstrating their compatibility with common amide/peptide coupling reagents and strategies. [Display omitted] •First synthesis of a pentafluorosulfanyl containing aromatic amino acid.•Amino acids were obtained through a Negishi cross-coupling strategy.•SPhos ligand was found to deliver a superior yield of the amino acids.•Two dipeptides with SF5 containing amino acids were prepared.•The SF5 containing aromatic amino acids are compatible with commonly utilised peptide synthesis and deprotection strategies Herein, a series of aromatic pentafluorosulfanyl (SF5) containing amino acids are reported. A Negishi cross-coupling strategy utilising a catalyst system of Pd(dba)2 and SPhos afforded the aforementioned SF5 amino acids in yields between 32% and 42%. Two dipeptides utilising both the amine and carboxylic functionalities of the synthesised SF5 containing amino acids were prepared, demonstrating their compatibility with common amide/peptide coupling reagents and strategies.