Heteroarylsilylation of Unactivated Alkenes

Heteroarylsilylation of Unactivated Alkenes

Author: Andrei Dragan

Organosilicon compounds are commonly used in materials science, energy development, and drug discovery. The radical-mediated silylation of alkenes provides a practical approach for production of organosilicon compounds. However, the silylation of unactivated alkenes is still very challenging.

Chen Zhu and colleagues, Soochow University, Suzhou, China, have developed a copper-catalyzed heteroarylsilylation of unactivated olefins via an intramolecular heteroaryl migration (pictured) which is triggered by the addition of silyl radicals to alkenes. The team used triphenylsilane as a silicon source, CuO as a catalyst, tert-butyl peroxyacetate to generate radicals, and 4-dimethylaminopyridine (DMAP) as a base.

The method can be used with a range of migrating heteroaryls, including benzothiazolyl, thiazolyl, imidazolyl, and pyridyl groups. The reactions proceed in synthetically useful yields, have good chemo- and regioselectivities, and tolerate a variety of functional groups. The approach allows the easy synthesis of heteroaryl-substituted alkyl silanes from readily available alkenes.


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