Department of Applied Chemistry, Graduate School of Science and Engineering, Saitma University, 255 Shimo-ohkubo, Sakura-ku, Saitama 338-8570, Japan.
Org Lett. 2011 Dec 2;13(23):6192-5. doi: 10.1021/ol202601s. Epub 2011 Nov 1.
The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential hydroalumination, alkene isomerization, carboalumination, carbon-carbon bond cleavage, and retro-hydroalumination.
二烷基氢化铝促进的 1-硅基-3-烯-1-炔反应得到对称的 1,2,3,5-四取代苯作为单一区域异构体。通过前所未有的机制可以合理地解释通过骨架重排的新型环二聚化，该机制涉及顺序氢化铝化、烯烃异构化、碳铝化、碳-碳键断裂和反氢化铝化。
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