Synthesis of Functionalized Furans via Chemoselective Reduction/Wittig Reaction Using Catalytic Triethylamine and Phosphine

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• 作者：Chia-Jui Lee ; Tzu-Hsiu Chang ; Jhen-Kuei Yu ; Ganapuram Madhusudhan Reddy ; Ming-Yu Hsiao ; Wenwei Lin
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3758-3761
• 全文大小：303K
• 年卷期：0
• ISSN：1523-7052

文摘

An efficient protocol for the synthesis of highly functionalized furans via intramolecular Wittig reaction has been developed using catalytic amounts of phosphine and triethylamine. Silyl chloride served as the initial promoter to activate the phosphine oxide. Reduction of the activated phosphine oxide by hydrosilane resulted in generation of phosphine, while decomposition of Et₃N·HCl resulted in regeneration of base, which mediated formation of phosphorus ylide. Remarkably, the in situ generated byproduct, Et₃N·HCl, also catalyzes reduction of phosphine oxide.