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Manganese-Catalyzed Regioselective C–H Lactonization and Hydroxylation of Fatty Acids with H2O2
Organic Letters ( IF 5.2 ) Pub Date : 2022-11-30 , DOI: 10.1021/acs.orglett.2c03458
Vladimir I Kurganskiy 1 , Roman V Ottenbacher 1 , Mikhail V Shashkov 1, 2 , Evgenii P Talsi 2 , Denis G Samsonenko 1, 3 , Konstantin P Bryliakov 1
Affiliation  

Herein, we report the direct selective C–H lactonization of fatty acids (C5–C16), catalyzed by manganese(II) complexes bearing bis-amino-bis-pyridine ligands. The catalyst system uses the environmentally benign hydrogen peroxide as oxidant and exhibits high efficiency (100–200 TON), providing under optimized conditions γ-lactones in 60–90% yields. Remarkably, by changing the reaction conditions, the oxidation of hexanoic acid can be diverted toward formation of δ-caprolactone in up to 67% yield. Furthermore, the possibility of obtaining (ω-1)-hydroxy derivatives from linear C7–C10 acids in up to 48% yields has been demonstrated.

中文翻译:

锰催化的区域选择性 C–H 内酯化和脂肪酸与 H2O2 的羟基化

在此,我们报道了由带有双氨基双吡啶配体的锰 (II) 配合物催化的脂肪酸 (C5–C16) 的直接选择性 C–H 内酯化。该催化剂系统使用对环境无害的过氧化氢作为氧化剂,具有高效率(100-200 TON),在优化条件下以 60-90% 的收率提供 γ-内酯。值得注意的是,通过改变反应条件,己酸的氧化可以转向形成 δ-己内酯,产率高达 67%。此外,已经证明了从线性 C7-C10 酸中以高达 48% 的产率获得 (ω-1)-羟基衍生物的可能性。
更新日期:2022-11-30
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