Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids

Grigolato, L.; Brittain, W.D.G.; Hudson, A.S.; Czyzewska, M.M; Cobb, S.L

doi:10.1016/j.jfluchem.2018.06.006

Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids

Grigolato, L.; Brittain, W.D.G.; Hudson, A.S.; Czyzewska, M.M; Cobb, S.L

Authors

L. Grigolato

Dr Will Brittain william.d.brittain@durham.ac.uk
Assistant Professor

A.S. Hudson

M.M Czyzewska

Professor Steven Cobb s.l.cobb@durham.ac.uk
Professor

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.

Citation

Grigolato, L., Brittain, W., Hudson, A., Czyzewska, M., & Cobb, S. (2018). Synthesis of pentafluorosulfanyl (SF5) containing aromatic amino acids. Journal of Fluorine Chemistry, 212, 166-170. https://doi.org/10.1016/j.jfluchem.2018.06.006

Journal Article Type	Article
Acceptance Date	Jun 15, 2018
Online Publication Date	Jun 18, 2018
Publication Date	Jun 18, 2018
Deposit Date	Jun 18, 2018
Publicly Available Date	Jun 26, 2018
Journal	Journal of Fluorine Chemistry
Print ISSN	0022-1139
Publisher	Elsevier
Peer Reviewed	Peer Reviewed
Volume	212
Pages	166-170
DOI	https://doi.org/10.1016/j.jfluchem.2018.06.006

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Copyright Statement
© 2018 The Authors. Published by Elsevier B.V. This is an open access article under the CC BY license (http://creativecommons.org/licenses/BY/4.0/).