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首页> 外文期刊>Chemistry: A European journal >Palladium-Catalyzed Intramolecular Hydroalkylation of Alkenyl-beta-Keto Esters,alpha-Aryl Ketones,and Alkyl Ketones in the Presence of Me_3SiCl or HC1
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Palladium-Catalyzed Intramolecular Hydroalkylation of Alkenyl-beta-Keto Esters,alpha-Aryl Ketones,and Alkyl Ketones in the Presence of Me_3SiCl or HC1

机译：Me_3SiCl或HC1存在下钯催化的烯基-β-酮酯，α-芳基酮和烷基酮的分子内加氢烷基化

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摘要

Reaction of 3-butenyl(3-keto esters or 3-butenyl alpha-aryl ketones with a catalytic amount of [PdCl_2(CH_3CN)_2](2)and a stoichiometric amount of Me_3SiCl or Me_3SiCl/CuO_2 in dioxane at 25-70 deg C formed 2-substituted cyclo-hexanones in good yield with high re-gioselectivity.This protocol tolerated a number of ester and aryl groups and tolerated substitution at the allylic,enolic,and cis and trans terminal ole-finic positions.In situ NMR experiments indicated that the chlorosilane was not directly involved in palladium-catalyzed hydroalkylation,but rather served as a source of HC1,which presumably catalyzes enolization of the ketone.Identification of HC1 as the active promoter of palladium-catatyzed hydroalkylation led to the development of an effective protocol for the hydroalkylation of alkyl 3-butenyl ketones that employed sub-stoichiometric amounts of 2,HC1,and CuCl_2 in a sealed tube at 70 deg C.
机译：3-丁烯基（3-酮酸酯或3-丁烯基α-芳基酮）与催化量的[PdCl_2（CH_3CN）_2]（2）和化学计量的Me_3SiCl或Me_3SiCl / CuO_2在二恶烷中的反应温度为25-70度C形成具有高收率和高区域选择性的2取代的环己酮。该方案耐受许多酯和芳基，并在烯丙基，烯醇，顺式和反式端烯烃末端位置耐受取代。表明氯硅烷不是直接参与钯催化的加氢烷基化反应，而是作为HCl的来源，推测可能是催化酮的烯醇化。烷基3-丁烯基酮加氢烷基化的实验方案，该实验在70℃的密闭管中使用了亚化学计量的2，HC1和CuCl_2。

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