I2 促进的 2-萘酚与甲基酮的选择性氧化交叉偶联/环化反应：构建具有季碳中心的萘[2,1-b]呋喃-1(2H)-酮的策略。

I2-promoted selective oxidative cross-coupling/annulation of 2-naphthols with methyl ketones: a strategy to build naphtho[2,1-b]furan-1(2H)-ones with a quaternary center.

机构信息

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, P. R. China.

出版信息

Org Lett. 2014 Mar 21;16(6):1732-5. doi: 10.1021/ol5004093. Epub 2014 Mar 3.

DOI:10.1021/ol5004093

PMID:24588728

Abstract

A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel-Crafts/oxidation/cyclization mechanism was proposed.

摘要

实现了一种高效、选择性的分子碘促进的 2-萘酚和甲基酮之间的氧化交叉偶联/环化反应。该反应成功地在 3(2H)-呋喃酮内构建了一个新的季碳原子中心。我们的合成策略提供了一种基于原位碘化的氧化偶联途径。根据实验结果，提出了一个自序列碘化/Kornblum 氧化/Friedel-Crafts/氧化/环化的反应机理。