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. 2018 Aug:212:166-170.
doi: 10.1016/j.jfluchem.2018.06.006.

Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids

Lucas Grigolato  1 , William D G Brittain  1 , Alex S Hudson  1 , Maria M Czyzewska  1 , Steven L Cobb  1
Affiliations

Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids

Lucas Grigolato et al. J Fluor Chem. 2018 Aug.

Abstract

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.

Keywords: Amino acid; Negishi cross-coupling; Pentafluorosulfanyl; SF5.

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Figures

None
Graphical abstract
Scheme 1
Scheme 1
Previously accessed SF5 containing amino acid, Welch and co-workers [25].
Fig. 1
Fig. 1
Crystal structure of compound 6S.
Scheme 2
Scheme 2
Formation of a dipeptide using SF5 amino acid 5R.
Scheme 3
Scheme 3
Formation of a dipeptide using SF5 amino acid 8R.
See this image and copyright information in PMC

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