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

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3758-3761
Number of pages4
JournalOrganic Letters
Volume18
Issue number15
DOIs
Publication statusPublished - 2016 Aug 5

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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

Cite this

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.

In: Organic Letters, Vol. 18, No. 15, 05.08.2016, p. 3758-3761.

Research output: Contribution to journalArticle

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. In: Organic Letters. 2016 ; Vol. 18, No. 15. pp. 3758-3761.
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