PtBr2-Catalyzed Transformation of Allyl(o-ethynylaryl)carbinol Derivatives into Functionalized Indenes. Formal sp3C−H Bond Activation
The Journal of Organic Chemistry2006Vol. 71(16), pp. 6204–6210
Citations Over TimeTop 10% of 2006 papers
Abstract
The PtBr2-catalyzed reaction of 1-ethynyl-2-(1-alkoxybut-3-enyl)benzenes at 120 degrees C in CH3CN gave functionalized indenes in good to allowable yields. Most probably, the hydrogen at the terminal alkyne is transferred to the adjacent internal beta-carbon to form an (eta2-vinylidene)platinum carbene intermediate, which activates the sp3 C-H bond at the benzylic carbon. This reaction pathway is supported by DFT calculations which suggest that the formation of the Pt-vinylidene complex is the rate-limiting stage for the whole transformation.
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