Metal-free sigmatropic rearrangement/cyclization/aromatization cascade reaction of hydroxy/aminophenyl propargyl alcohols with fluoroalkanesulfinyl chlorides: Synthesis of 3‑fluoroalkanesulfonyl benzofurans and indoles
Si-Jing Jiang, Zhao-Zhao Li, Li-Na Yang, Ming Bian, Xiao-Han Qiu, Yu-Ning Gao, Hui-Yu Chen, Zhen-Jiang Liu
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引用次数: 0
Abstract
A metal-free protocol to synthesize 2-alkyl-3‑fluoroalkanesulfonyl benzofurans and indoles from o‑hydroxyphenyl/o‑aminophenyl propargyl alcohols or 2-propynolphenols/2-propynolanilines and fluoroalkanesulfinyl chlorides (RFSOCl) was disclosed. The mechanism is proposed to involve a sequential [1,2]/[2,3]-sigmatropic rearrangement/intramolecular oxy-addition/1,3-H migration cascade of the propargyl triflinates generated in situ via O-fluoroalkanesulfinylation of propargyl alcohols. The procedure utilizes readily available propargyl alcohols and RFSOCl as starting materials and offers a broad substrate scope with excellent performance (55 examples, up to 98% yield).
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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