(NHC)Ni(II)催化的[3+2]氢烯化重排串联反应的应用

doi:10.6023/cjoc202005050

摘要/Abstract

着重研究近期发展的环张力烯烃[3+2]氢烯化重排串联反应（HARC）在合成方面的应用，比较了此类多取代环戊二烯和亚甲基环戊烷的合成机理与传统烯烃和二烯交叉氢烯化反应的不同，并以环化产物为关键原料，进行了包括Diels-Alder、环氧化、臭氧解、卤代重排和氟羟基化等一系列衍生化，一步或多步串联制备了具有高度非对映选择性的、传统方法难以获取的若干有趣且复杂的碳骨架产物.

关键词: 张力烯烃, [3+2]环加成, 氮杂环卡宾, 镍催化, 交叉氢烯化

Synthetic applications of the recently developed (NHC)Ni(Ⅱ) catalyzed[3+2] hydroalkenylation-rearrangement cascade (HARC) were investigated. The foundations of these highly substituted cyclopentadienes and methylene cyclopentanes formation were compared with typical cross-hydroalkenylation of alkenes and dienes. The desired cyclization products were examined as key starting materials for a range of olefin functionalization methodology, including Diels-Alder, epoxidation, ozonolysis, halogenation-rearrangement and fluorohydroxylation. The results showed that several very interesting carbon skeletons can be obtained easily with high diastereoselectivity in one step or in cascade.

Key words: strained alkene, [3+2] cycloaddition, N-heterocycle carbenes, Ni catalysis, cross-hydroalkenylation

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雍学锋, 黄建强, 何振宇. (NHC)Ni(II)催化的[3+2]氢烯化重排串联反应的应用[J]. 有机化学, 2020, 40(10): 3327-3337.

Yong Xue-Feng, Huang Jian-Qiang, Ho Chun-Yu. Applications of (NHC)Ni(II) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3327-3337.

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