Batch and Flow Synthesis of Disulfides by Visible-Light-Induced TiO2 Photocatalysis

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• 作者：Cecilia Bottecchia ; Dr. Nico Erdmann ; Patricia M. A. Tijssen ; Dr. Lech-Gustav Milroy ; Prof. Dr. Luc Brunsveld ; Prof. Dr. Volker Hessel and Dr. Timothy Noë ; l
• 刊名：ChemSusChem
• 出版年：2016
• 出版时间：July 21, 2016
• 年：2016
• 卷：9
• 期：14
• 页码：1781-1785
• 全文大小：747K
• ISSN：1864-564X

文摘

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.