Issue 32, 2017
From the journal:

Chemical Communications

Pyreneacyl sulfides as a visible light-induced versatile ligation platform†

Bryan T. Tuten,abc   Jan P. Menzel,abc   Kai Pahnke,ab   James P. Blinco ORCID logo *ac  and  Christopher Barner-Kowollik ORCID logo *abc  

* Corresponding authors

a Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany
E-mail: christopher.barner-kowollik@kit.edu

b Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany

c School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, Brisbane, Australia
E-mail: j.blinco@qut.edu.au, christopher.barnerkowollik@qut.edu.au

Abstract

We report a visible light responsive moiety capable of generating highly reactive thioaldehydes. Upon irradiation with visible light (420 nm) the pyreneacyl sulfide species undergoes a Norrish II elimination yielding thioaldehydes capable of being trapped by nucleophiles (amines, aminoxys, and thiols), as well as Diels–Alder processes, representing a new versatile ligation platform.

Graphical abstract: Pyreneacyl sulfides as a visible light-induced versatile ligation platform

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Article information

DOI
https://doi.org/10.1039/C7CC00711F
Article type
Communication
Submitted
25 Jan 2017
Accepted
28 Mar 2017
First published
28 Mar 2017

Chem. Commun., 2017,53, 4501-4504

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Pyreneacyl sulfides as a visible light-induced versatile ligation platform

B. T. Tuten, J. P. Menzel, K. Pahnke, J. P. Blinco and C. Barner-Kowollik, Chem. Commun., 2017, 53, 4501 DOI: 10.1039/C7CC00711F

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