Hydro/Deutero Deamination of Arylazo Sulfones under Metal- and (Photo)Catalyst-Free Conditions

Hawraz I M Amin; Carlotta Raviola; Ahmed A Amin; Barbara Mannucci; Stefano Protti; Maurizio Fagnoni

doi:10.3390/molecules24112164

Hydro/Deutero Deamination of Arylazo Sulfones under Metal- and (Photo)Catalyst-Free Conditions

Molecules. 2019 Jun 8;24(11):2164. doi: 10.3390/molecules24112164.

Authors

Hawraz I M Amin^{1

2}, Carlotta Raviola³, Ahmed A Amin⁴, Barbara Mannucci⁵, Stefano Protti⁶, Maurizio Fagnoni⁷

Affiliations

¹ PhotoGreen Lab, Department of Chemistry, University of Pavia. Viale Taramelli 12, 27100 Pavia, Italy. hawraz_px@yahoo.com.
² Chemistry Department, College of Science, Salahaddin University-Erbil, Erbil 44001, Iraq. hawraz_px@yahoo.com.
³ PhotoGreen Lab, Department of Chemistry, University of Pavia. Viale Taramelli 12, 27100 Pavia, Italy. carlotta.raviola01@universitadipavia.it.
⁴ Chemistry Department, College of Education, Salahaddin University-Erbil, Erbil 44001, Iraq. ahmed.dezaye@su.edu.krd.
⁵ Centro Grandi Strumenti (CGS), University of Pavia, V. Bassi 21, 27100 Pavia, Italy. barbara.mannucci@unipv.it.
⁶ PhotoGreen Lab, Department of Chemistry, University of Pavia. Viale Taramelli 12, 27100 Pavia, Italy. stefano.protti@unipv.it.
⁷ PhotoGreen Lab, Department of Chemistry, University of Pavia. Viale Taramelli 12, 27100 Pavia, Italy. fagnoni@unipv.it.

Abstract

Hydrodeaminated and monodeuterated aromatics were obtained via a visible-light driven reaction of arylazo sulfones. Deuteration occurs efficiently in deuterated media such as isopropanol-d⁸ or in THF-d⁸/water mixtures and exhibits a high tolerance to the nature and the position of the aromatic substituents.

Keywords: arylazo sulfones; deuteration; photochemistry; visible-light induced processes.

MeSH terms

Carbon-13 Magnetic Resonance Spectroscopy
Catalysis
Deamination
Deuterium / chemistry*
Hydrogen / chemistry*
Light*
Metals / chemistry*
Proton Magnetic Resonance Spectroscopy
Sulfones / chemistry*

Substances

Metals
Sulfones
Hydrogen
Deuterium