ol6b01781_si_001.pdf (3.67 MB)
Synthesis of Functionalized Furans via Chemoselective Reduction/Wittig Reaction Using Catalytic Triethylamine and Phosphine
journal contribution
posted on 2016-07-19, 12:35 authored by Chia-Jui Lee, Tzu-Hsiu Chang, Jhen-Kuei Yu, Ganapuram Madhusudhan Reddy, Ming-Yu Hsiao, Wenwei LinAn
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.