Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and ¹⁵N₂-Diazirines and Their Application as Hyperpolarized Markers

Thomas Glachet, Hamid Marzag, Nathalie Saraiva Rosa, Johannes F. P. Colell, Guannan Zhang, Warren S. Warren, Xavier Franck, Thomas Theis*, Vincent Reboul*

*North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States; Normandie Univ, 14000 Caen, France, Email: ttheisncsu.edu, vincent.reboulensicaen.fr

T. Glachet, H. Marzag, N. S. Rosa, J. F. P. Colell, G. Zhang, W. S. Warren, X. Franck, T. Theis, V. Reboul, J. Am. Chem. Soc., 2019, 141, 13689-13696.

DOI: 10.1021/jacs.9b07035

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Abstract

The use of phenyliodonium diacetate (PIDA) and ammonia enables a one-pot metal-free conversion of unprotected amino acids to terminal diazirines. This method tolerates a broad range of functional groups, is operationally simple, and can be scaled up to provide multigram quantities of diazirine.

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proposed mechanism

Synthesis of ¹⁵N₂-Diazirines from Unlabeled Amino Acids

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Key Words

diazirines, PIDA

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ID: J48-Y2019