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锰催化环丁醇开环的C—C键氟化反应(英文)

Manganese-Catalyzed Ring-Opening C—C Bond Fluorination of Cyclobutanols

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【作者】 王丽梅; 刘晓圆; 昝金成; 孙书涛; 刘磊; 李伟; 刘希功;

【Author】 Wang Limei;Liu Xiaoyuan;Zan Jincheng;Sun Shutao;Liu Lei;Li Wei;Liu Xigong;School of Pharmacy, Shandong University of Traditional Chinese Medicine;School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University;School of Chemistry and Chemical Engineering, Shandong University;

【通讯作者】 刘磊;李伟;刘希功;

【机构】 山东中医药大学药学院; 山东第一医科大学药学院(药物研究所); 山东大学化学与化工学院;

【摘要】 锰因其相对丰度高、价格低廉、环境友好等特点而在催化环丁醇的C—C键断裂官能化反应研究中备受关注.报道了一例锰催化环丁醇开环C—C键氟化反应.该反应在温和的条件下,以10 mol%的Mn(OAc)2作为催化剂, HF·Et3N和PhIO作用原位生成的亲电氟化试剂作为氟源,为直接合成γ-氟化酮提供了一种有效的途径.该反应具有优异的官能团耐受性,并显示出广泛的底物范围,能够以50%~76%的产率得到相应的产物.

【Abstract】 Manganese-catalyzed C—C bond cleavage of cyclobutanols has attracted great attention due to the high abundance and cheap and eco-friendly behaviour. A manganese-catalyzed ring-opening C—C bond fluorination of cyclobutanols is reported. Under mild conditions, the reaction provides a straightforward access to γ-fluorinated ketones using 10 mol% Mn(OAc)2 as catalyst and electrophilic fluorination reagent, which was generated in situ from HF·Et3N and PhIO, as fluorine source. The reaction has an excellent functional-group tolerance and displays a broad substrate scope, affording the corresponding products in 50%~76% yields.

【基金】 Project supported by the National Natural Science Foundation of China(Nos.92156008,22161142016);the Taishan Scholar Program at Shandong Province;the Natural Science Foundation of Shandong Province(No.ZR2020QB018)~~
  • 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2024年07期
  • 【分类号】O621.251
  • 【下载频次】4
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