金催化炔基酯和酮的氟化反应：高效合成氟化1,3 - 二羰基化合物
Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds.
作者信息
Zeng Xiaojun, Lu Zhichao, Liu Shiwen, Hammond Gerald B, Xu Bo
机构信息
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China.
Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
出版信息
Adv Synth Catal. 2017 Nov 23;359(22):4062-4066. doi: 10.1002/adsc.201701179. Epub 2017 Oct 5.
Abstract
We developed an efficient synthesis of 2-fluoro-1,3-dicarbonyl compounds using readily available alkynyl ketones or esters as starting material. The key step is the insertion of hydrogen fluoride (HF) to the gold carbene intermediate generated from cationic gold catalyzed addition of -oxides to alkynyl ketones or esters. This method gives excellent chemical yields and regioselectivity with good functional group tolerance.
摘要
我们以易于获得的炔基酮或酯为起始原料，开发了一种高效合成2-氟-1,3-二羰基化合物的方法。关键步骤是将氟化氢（HF）插入由阳离子金催化的α-氧化物与炔基酮或酯加成反应生成的金卡宾中间体中。该方法具有优异的化学产率和区域选择性，且对官能团具有良好的耐受性。
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