title: Batch and Flow Synthesis of Disulfides by Visible-Light-Induced TiO2 Photocatalysis.
abstract: A mild and practical method for the preparation of disulfides through visible-light-induced photocatalytic aerobic oxidation of thiols has been developed. The method involves the use of TiO2 as a heterogeneous photocatalyst. The catalyst's high stability and recyclability makes this method highly practical. The reaction can be substantially accelerated in a continuous-flow packed-bed reactor, which enables a safe and reliable scale-up of the reaction conditions. The batch and flow protocol described herein can be applied to a diverse set of thiol substrates for the preparation of homo- and hetero-dimerized disulfides. Furthermore, biocompatible reaction conditions (i.e., room temperature, visible light, neutral buffer solution, and no additional base) have been developed, which permits the rapid and chemoselective modification of densely functionalized peptide substrates without recourse to complex purification steps.
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Cecilia
authors.initials: C
authors.lastname: Bottecchia
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Nico
authors.initials: N
authors.lastname: Erdmann
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Patricia M A
authors.initials: PM
authors.lastname: Tijssen
authors.affiliation: Laboratory of Chemical Biology and, Institute of Complex Molecular Systems (ICMS), Department of Biomedical Engineering, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Lech-Gustav
authors.initials: LG
authors.lastname: Milroy
authors.affiliation: Laboratory of Chemical Biology and, Institute of Complex Molecular Systems (ICMS), Department of Biomedical Engineering, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Luc
authors.initials: L
authors.lastname: Brunsveld
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands.
authors.forename: Volker
authors.initials: V
authors.lastname: Hessel
authors.affiliation: Department of Chemical Engineering and Chemistry, Micro Flow Chemistry & Process Technology, Eindhoven University of Technology, Den Dolech 2, 5612 AZ, Eindhoven, The Netherlands. t.noel@tue.nl.
authors.forename: Timothy
authors.initials: T
authors.lastname: Noël
mesh_terms: D019149:Bioreactors; D002384:Catalysis; D004220:Disulfides / Q000737:chemistry*; D008027:Light; D055668:Photochemical Processes; D014025:Titanium / Q000737:chemistry*
chemical_list: D004220:Disulfides; C009495:titanium dioxide; D014025:Titanium
keywords: continuous flow; disulfide formation; heterogeneous photocatalysis; titanium dioxide; visible light