TY - JOUR
T1 - Batch and flow synthesis of disulfides by visible-light-induced TiO2 photocatalysis
AU - Bottecchia, C.
AU - Erdmann, N.
AU - Tijssen, P.M.A.
AU - Milroy, L.G.
AU - Brunsveld, L.
AU - Hessel, V.
AU - Noël, T.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
U2 - 10.1002/cssc.201600602
DO - 10.1002/cssc.201600602
M3 - Article
C2 - 27329945
SN - 1864-5631
VL - 9
SP - 1781
EP - 1785
JO - ChemSusChem
JF - ChemSusChem
IS - 14
ER -