Acid Catalyzed Formation of C⁻C and C⁻S Bonds via Excited State Proton Transfer

Alessandro Strada; Mattia Fredditori; Giuseppe Zanoni; Stefano Protti

doi:10.3390/molecules24071318

Acid Catalyzed Formation of C⁻C and C⁻S Bonds via Excited State Proton Transfer

Molecules. 2019 Apr 3;24(7):1318. doi: 10.3390/molecules24071318.

Authors

Alessandro Strada¹, Mattia Fredditori^{2

3}, Giuseppe Zanoni⁴, Stefano Protti⁵

Affiliations

¹ Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy. alessandro.strada02@universitadipavia.it.
² Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy. mattia.fredditori01@universitadipavia.it.
³ PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy. mattia.fredditori01@universitadipavia.it.
⁴ Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy. gz@unipv.it.
⁵ PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy. stefano.protti@unipv.it.

Abstract

The behavior of 2-naphthol and 7-bromo-2-naphthol as organic photoacids are exploited in organic synthesis for the preparation of benzyl sulfides (using a trichloroacetimidate derivative as the starting substrate) and polycyclic amines via acid catalyzed condensation of 1,2,3,4-tetrahydroisoquinoline with aldehydes.

Keywords: acid catalyzed synthesis; excited state proton transfer; photocatalysis; tris(bipyridine)ruthenium(II) chloride.

MeSH terms

Acids / chemistry*
Alkaloids / chemical synthesis
Alkaloids / chemistry
Benzyl Compounds / chemical synthesis
Benzyl Compounds / chemistry
Catalysis
Protons*

Substances

Acids
Alkaloids
Benzyl Compounds
Protons
benzyl sulfide