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Published on: April 22, 2016
Visible Light Thiyl Radical-Mediated Desilylation of Arylsilanes
Jan H Kuhlmann1, Jan H Dickoff1, Olga García Mancheño1
1Organic Chemistry Institute, University of Münster, Corrensstraße 36, 48149, Münster, Germany.
Abstract:
A straightforward, visible-light triggered desilylation of arylsilanes by thiyl radicals is presented. Silyl groups are often used to block a reactive position in multi-step organic synthesis, for which a mild cleavage at a late-stage will provide new possibilities and disconnection routes by CAr -Si cleavage/deprotection. In this work, commercially available and cheap disulfides are employed for the first time in this type of C(sp2 )-Si bond cleavage reactions. Thus, upon irradiation with visible-light, homolytic cleavage of the disulfide give rise to the corresponding thiyl radical that allows for a radical chain mechanism. This methodology represents a mild, fast and simple approach suitable for a broad variety of simply substituted arylsilanes. Moreover, the procedure could be easily extended to natural products and therapeutic derivatives, showing its robustness and synthetic application potential.
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