三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化

doi:10.6023/cjoc202005025

有机化学 ›› 2020, Vol. 40 ›› Issue (11): 3908-3915.DOI: 10.6023/cjoc202005025 上一篇下一篇

所属专题：创刊四十周年专辑

研究论文

三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化

吴毅^a, 肖元晶^a, 张俊良^a,b

a 华东师范大学化学与分子工程学院上海市绿色化学与化学工程绿色化重点实验室上海 200062;
b 复旦大学化学系上海 200438

收稿日期:2020-05-10 修回日期:2020-06-08 发布日期:2020-07-01
通讯作者: 肖元晶, 张俊良 E-mail:yjxiao@chem.ecnu.edu.cn;jlzhang@chem.ecnu.edu.cn
基金资助:
国家自然科学基金（Nos.21372084，21425205，21871093）、教育部长江学者和创新团队发展计划和国家重点基础研究发展计划（973计划，No.2015CB-856600）资助项目.

BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones

Wu Yi^a, Xiao Yuanjing^a, Zhang Junliang^a,b

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b Department of Chemistry, Fudan University, Shanghai 200438

Received:2020-05-10 Revised:2020-06-08 Published:2020-07-01
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372084, 21425205, 21871093), the Program for Changjiang Scholars and Innovative Research Team in University of Ministry of Education and the National Basic Research Program of China (973 Program, No. 2015CB-856600).

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摘要/Abstract

发展了一种无金属作用，以三氯化硼为介导的对2-（1-炔基）-2-烯烃-1-酮的硼酸酯化环化，有效合成具有多官能的萘硼酸酯化合物.产物中存在的硼酸酯官能团能够进行多样化的衍生化.该方法具有操作简单、中等至良好的收率、易于克级规模制备且能实现多种合成转化的优点.同时，该工作开发了2-（1-炔基）-2-烯烃-1-酮的新合成应用.

关键词: 无金属, 硼酸酯化, 环化, 萘硼酸酯, 转化

A metal-free, BCl₃ mediated borylative cyclization of 2-(1-alkynyl)-2-alken-1-ones leading to synthetic valuable multi-functionalized naphthalene boronates in one step was developed. The boronate functionality present in the product provides many opportunities for derivatization. The salient features of this reaction include moderate to good yields, gram-scale synthesis and diverse synthetic transformations. In the meantime, the new synthetic applications of 2-(1-alkynyl)-2-alken-1-ones have been developed.

Key words: metal free, borylative, cycliazation, naphthalene boronates, transformations

引用此文

吴毅, 肖元晶, 张俊良. 三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化[J]. 有机化学, 2020, 40(11): 3908-3915.

Wu Yi, Xiao Yuanjing, Zhang Junliang. BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3908-3915.

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三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化

BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones

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三氯化硼为介导的2-(1-炔基)-2-烯烃-1-酮的硼酸酯化环化

BCl3 Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones

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BCl₃ Mediated Borylative Cyclization of 2-(1-Alkynyl)-2-alken-1-ones