研究室工作进展 Aug 13th, 2012

Construction of Benzosiloles, Six- and Eight-Membered Silacyclic Skeletons via a Pd-Catalyzed Intramolecular Mizoroki-Heck Reaction of Vinylsilanes

Kunbing Ouyang, Yun Liang, and Zhenfeng Xi*

 Org. Lett. 2012, DOI: 10.1021/ol302040j

Silicon possesses some crucial differences from carbon (eg. covalent radius and electro-negativity). Thus, when a carbon atom is replaced by a silicon atom (the C/Si switch strategy), the chemical and physicochemical properties of an organic compound may be changed dramatically. For example, silacyclopentadiene (often named silole) as organic material of electronic and opto-electronic devices demonstrates much superiority to its carbon-analogue, cyclopentadiene. In particular, the C/Si switch strategy has been applied successfully for odorant design and pharmaceutical applications. Furthermore, specific properties can be expected from totally new silicon-containing compounds, of which the carbon analogues cannot be synthesized or are very difficult to make. Thus, as a consequence, the development of synthetic methods for silacyclic compounds remains one of the most important frontiers in synthetic chemistry.

In this work, a variety of silacycles including benzosiloles, 6-, and 8-membered silacyclic skeletons were efficiently synthesized via a Pd-catalyzed intramolecular Mizoroki-Heck reaction of vinylsilanes.