试剂控制的螺环氧吲哚亲核氟化区域选择性反转：3-氟-3-羟甲基吲哚和 3-芳基-3-氟甲基吲哚的合成。
Reagent-Controlled Reversal of Regioselectivity in Nucleophilic Fluorination of Spiro-epoxyoxindole: Synthesis of 3-Fluoro-3-hydroxymethyloxindole and 3-Aryl-3-fluoromethyloxindole.
机构信息
Center of Biomedical Research , Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road , Lucknow 226014 , India.
Department of Chemistry , Indian Institute of Technology Kharagpur , Kharagpur 721302 , India.
出版信息
J Org Chem. 2019 Feb 15;84(4):2252-2260. doi: 10.1021/acs.joc.9b00059. Epub 2019 Feb 1.
A convenient and metal/catalyst-free approach for the reversal of regioselectivity in nucleophilic fluorination of a wide range of spiro-epoxyoxindoles has been reported simply by altering the nucleophilic fluoride reagents. Py·(HF) -mediated fluorination at the tertiary sp-C center of spiro-epoxyoxindole furnishes 3-fluoro-3-hydroxymethyloxindoles, whereas TBAF-mediated fluoride addition at the primary sp-C center renders 3-fluoromethyl-3-hydroxyoxindoles, which have been utilized for the synthesis of 3-aryl-3-fluoromethyloxindole.
一种简便且无需金属/催化剂的方法，通过改变亲核氟试剂，实现了对一系列螺环氧氧吲哚的亲核氟化反应区域选择性的反转。在螺环氧氧吲哚的叔 C 中心，Py·（HF）介导的氟化反应生成 3-氟-3-羟甲基氧化吲哚，而 TBAF 介导的氟加成反应则在伯 C 中心生成 3-氟甲基-3-羟基氧化吲哚，这些产物被用于合成 3-芳基-3-氟甲基氧化吲哚。
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