有机化学 ›› 2015, Vol. 35 ›› Issue (3): 655-661.DOI: 10.6023/cjoc201412009 上一篇    下一篇

研究论文

金催化分子间氧化炔酰胺合成α-氨基酰胺

李龙, 周波, 叶龙武   

  1. 固体表面物理化学国家重点实验室 福建省化学生物学重点实验室 厦门大学化学化工学院 厦门 361005
  • 收稿日期:2014-12-03 修回日期:2014-01-01 发布日期:2014-01-09
  • 通讯作者: 叶龙武 E-mail:longwuye@xmu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21102119, 21272191)和教育部创新团队资助项目.

Efficient and Practical Synthesis of α-Amino Amides through Gold-Catalyzed Intermolecular Oxidation of Ynamides

Li Long, Zhou Bo, Ye Longwu   

  1. State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005
  • Received:2014-12-03 Revised:2014-01-01 Published:2014-01-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21102119, 21272191) and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT).

α-氨基酰胺作为一类重要的羰基化合物广泛存在于众多天然的和非天然的生物活性分子之中. 本工作实现了芳胺NH对在水相体系中通过金催化的分子间氧化炔烃途径产生的α-羰基金卡宾的插入反应. 这种通过非重氮方式产生α-羰基金属卡宾的策略为有效合成多种官能团化的α-氨基酰胺化合物提供了一种通用且实用的方法.

关键词: 金催化, α-氨基酰胺, 金卡宾, 氧化反应

α-Amino amides constitute an important category of carbonyl compounds which exist in a large number of bioactive natural and non natural molecules. In this paper, an efficient intermolecular reaction of gold carbene intermediates, generated through gold-catalyzed intermolecular oxidation of alkynes, with primary anilines has been realized in aqueous media. Importantly, this non-diazo approach provides a general and practical solution for the synthesis of various functionalized α-amino amides.

Key words: gold catalysis, α-amino amides, gold carbenoids, oxidation