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

Chia Jui Lee, Tzu Hsiu Chang, Jhen Kuei Yu, Ganapuram Madhusudhan Reddy, Ming Yu Hsiao, Wen-Wei Lin

研究成果: 雜誌貢獻文章

27 引文 (Scopus)

摘要

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.

原文英語
頁(從 - 到)3758-3761
頁數4
期刊Organic Letters
18
發行號15
DOIs
出版狀態已發佈 - 2016 八月 5

指紋

phosphine
Furans
furans
phosphines
Oxides
synthesis
oxides
regeneration
Phosphorus
Byproducts
phosphorus
Chlorides
Regeneration
chlorides
triethylamine
Decomposition
decomposition

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

引用此文

Synthesis of Functionalized Furans via Chemoselective Reduction/Wittig Reaction Using Catalytic Triethylamine and Phosphine. / Lee, Chia Jui; Chang, Tzu Hsiu; Yu, Jhen Kuei; Madhusudhan Reddy, Ganapuram; Hsiao, Ming Yu; Lin, Wen-Wei.

於: Organic Letters, 卷 18, 編號 15, 05.08.2016, p. 3758-3761.

研究成果: 雜誌貢獻文章

Lee, Chia Jui ; Chang, Tzu Hsiu ; Yu, Jhen Kuei ; Madhusudhan Reddy, Ganapuram ; Hsiao, Ming Yu ; Lin, Wen-Wei. / Synthesis of Functionalized Furans via Chemoselective Reduction/Wittig Reaction Using Catalytic Triethylamine and Phosphine. 於: Organic Letters. 2016 ; 卷 18, 編號 15. 頁 3758-3761.
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AU - Lin, Wen-Wei

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