B(CF)₃·H₂O催化的无金属条件下芳胺与硫叶立德的N-H和C-H官能化反应
B(CF)·HO-Catalyzed N-H and C-H Functionalization of Aromatic Amines with Sulfoxonium Ylides under Metal-Free Conditions.
作者信息
Yan Shenmeng, Hao Yingdi, Xu Shuran, Hai Li, Lv Guanghui, Wu Yong
机构信息
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17, Third Section, South Renmin Road, Chengdu, 610041 Sichuan, P. R. China.
Department of Pharmacy, Hubei Provincial Clinical Research Center for Umbilical Cord Blood Hematopoietic Stem Cells, Taihe Hospital, Hubei University of Medicine, Shiyan, 442000 Hubei, China.
出版信息
J Org Chem. 2024 Sep 20;89(18):13401-13411. doi: 10.1021/acs.joc.4c01558. Epub 2024 Aug 31.
Hydrogen-bonded aggregates of B(CF) and water are proven as strong Brønsted acid catalysts, which have the advantages of low toxicity and broad compatibility. Sulfoxonium ylides are stable surrogates of diazo compounds, which participate in various reactions due to their versatile reactivity. Based on these characteristics, a strategy for C-N bond or C-C bond construction of aromatic amines with sulfoxonium ylides under metal-free catalytic conditions was established. This method has advantages of mild conditions and excellent yield, which is suitable for the N-H or C-H functionalization of various aromatic amine compounds.
已证实B(CF)与水形成的氢键聚集体是强布朗斯特酸催化剂，具有低毒性和广泛兼容性的优点。锍叶立德是重氮化合物的稳定替代物，由于其反应活性多样，可参与各种反应。基于这些特性，建立了一种在无金属催化条件下用锍叶立德构建芳香胺C-N键或C-C键的策略。该方法具有条件温和、产率优异的优点，适用于各种芳香胺化合物的N-H或C-H官能化。
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