An Alternative to Precious Metals: Hg(ClO4)(2)center dot 3H(2)O as a Cheap and Water-Tolerant Catalyst for the Cycloisomerization of Allenols

作者：Alcaide Benito^*; Almendros Pedro; Luna Amparo; Soriano Elena

来源：Journal of Organic Chemistry, 2015, 80(14): 7050-7057.

DOI：10.1021/acs.joc.5b00887

Hg(ClO4)(2)center dot 3H(2)O, a cheap, water-tolerant, and stable salt, catalyzes the cydoisomerization reaction or alpha-allenols to 2,5-dihydrofurans in an efficient and selective manner. The reaction is general and can be applied to differently functionalized substrates, including alkyl-substituted, aryl-substituted, enantiopure, and tertiary allenols. In addition, density functional theory (DFT) calculations were performed to obtain insight into various aspects of the controlled reactivity of a-allenols under mercury catalysis. They suggest a dual activation of the allenol by the Hg complex that drives the reaction to the chemoselective formation of 2,5-dihydrofurans.

• 出版日期2015-7-17