A Novel Synthetic Route to 2-ArylalkanoicAcids by a Ruthenium-Catalyzed Chemoselective Oxidation of FuranRings
A Novel Synthetic Route to 2-ArylalkanoicAcids by a Ruthenium-Catalyzed Chemoselective Oxidation of FuranRings
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钌催化呋喃环化学选择性氧化合成 2-芳基烷酸的新路线
DOI：
10.1055/s-0028-1083222
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发表时间：
2008
期刊：
影响因子：
--
通讯作者：
K. Ishii
中科院分区：
文献类型：
--
作者：
Masahiro Noji;Haruka Sunahara;K. Tsuchiya;T. Mukai;Ayako Komasaka;K. Ishii
报道了由1-芳基烷醇两步合成2-芳基烷酸的方法。首先，通过金属三氟甲磺酸盐催化的2-甲基呋喃与1-芳基烷醇的Friedel-Crafts烷基化反应，在无水条件下高产率地合成了1-芳基烷基呋喃衍生物。然后研究了1-芳烷基呋喃中呋喃环的化学选择性氧化成羧酸。在正己烷-乙酸乙酯/水（1：3：4）溶剂体系中，以0.5mol%RuCl3为催化剂，用7当量NaIO 4选择性氧化呋喃环，得到2-芳基烷酸。钌氧化的选择性由正己烷-乙酸乙酯的溶剂比控制。
An efficient two-step synthesis of 2-arylalkanoic acids from 1-arylalkanols is described. Firstly, 1-arylalkylfuran derivatives were synthesized in high yields by the metal triflate catalyzed Friedel-Crafts alkylation of 2-methylfuran with 1-arylalkanols without employing anhydrous conditions. The chemoselective oxidation of the furan ring in 1-arylalkylfurans to carboxylic acid was then investigated. In a solvent system of hexane-EtOAc/H 2 O (1:3:4), the furan ring was selectively oxidized with 7 equivalents of NaIO 4 by using 0.5 mol% RuCl 3 as catalyst to give 2-arylalkanoic acids in good yields. The selectivity of ruthenium oxidation was controlled by the solvent ratio of hexane-EtOAc.