钯催化苄基硼酸酯与3-碘代氮杂环丁烷的偶联反应研究

发布时间：2018-04-30 23:41

本文选题：苄基硼酸频哪醇酯 + N-Boc-3-碘代氮杂环丁烷　；参考：《郑州大学》2017年硕士论文

【摘要】：本文首先合成了一系列的含有不同取代基的苄基硼酸频哪醇酯,并将其应用于构建C(sp3)-C(sp3)键的Suzuki偶联反应中,区域选择性地合成了一系列的α-苄基吖丁啶类化合物。1.苄基硼酸频哪醇酯及其衍生物的制备在钯催化下,利用取代苄溴和联硼酸频哪醇酯的偶联反应,通过对反应温度的研究与控制,以中等左右收率合成了18种取代的苄基硼酸频哪醇酯(Scheme 1)。Scheme 1 The synthesis of Benzylboronic acid pinacol ester and its derivatives2.N-Boc-3-碘代氮杂环丁烷和苄基硼酸频哪醇酯的交叉偶联反应以苄基硼酸频哪醇酯和N-Boc-3-碘代氮杂环丁烷的交叉偶联反应为模板,通过考察钯源、配体、碱、溶剂、温度、时间对反应的影响,发现以Pd(COD)Cl2和RuPhos为催化剂、碳酸铯为碱、1,4-二氧六环/水(V:V=1:1)为溶剂,在80℃反应24小时为最优条件。并在最优条件下进行了底物拓展,以中等到较好的收率合成了16个α-苄基吖丁啶类化合物(Scheme 2)。Scheme 2 The synthesis of α-Benzyl azetidines
[Abstract]:A series of benzyl boric acid esters containing different substituents were synthesized and applied to the Suzuki coupling reaction of the C (SP3) -C (SP3) bond. A series of benzyl acridine compounds,.1. benzyl boric acid, alkyl alcohol ester and its derivatives were synthesized in the region, and the preparation of substituted benzyl groups under the catalysis of palladium and the use of substituted benzyl The coupling reaction of bromine and boric acid alkyl alcohol ester, through the study and control of the reaction temperature, 18 substituted benzyl boric acid alkyl alcohol ester (Scheme 1).Scheme 1 The synthesis of Benzylboronic acid pinacol ester and its derivatives2.N-Boc-3- iodized heterocyclane and benzyl boric acid esters of alkyl alcohol ester are synthesized by the study and control of reaction temperature. The cross coupling reaction of the cross coupling reaction with the cross coupling reaction of benzyl borate and N-Boc-3- iodibutanobutane was used as a template. By investigating the effect of palladium source, ligand, alkali, solvent, temperature and time on the reaction, we found that Pd (COD) Cl2 and RuPhos as the catalyst, caesium carbonate as base, 1,4- two oxygen six ring / water (V:V=1:1) as solvent and 24 hour reaction at 80. Under the optimal conditions, the substrate was extended and 16 alpha benzyl acridine compounds (Scheme 2).Scheme 2 The synthesis of alpha -Benzyl Azetidines were synthesized in a medium and good yield.

【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251

【相似文献】