Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1218-1225.DOI: 10.6023/cjoc202310023 Previous Articles     Next Articles

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银催化邻羟基苯基炔丙醇5-exo-dig环化反应构筑2-亚甲基-2,3-二氢苯并呋喃-3-醇

冯淼, 吕兰兰*(), 郭一佳, 刘建全, 王香善*()   

  1. 江苏师范大学化学与材料科学学院 江苏徐州 221116
  • 收稿日期:2023-10-24 修回日期:2023-12-08 发布日期:2023-12-28
  • 基金资助:
    江苏省高校面上项目(22KJD150003); 2023年度江苏师范大学实验室研究课题(L2023YB08)

Silver-Catalyzed 5-Exo-dig Cyclization Reaction of ortho-Hydroxyphenylpropargyl Alcohols to 2-Methylene-2,3-dihydrobenzofuran

Miao Feng, Lanlan Lü(), Yijia Guo, Jianquan Liu, Xiangshan Wang()   

  1. School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
  • Received:2023-10-24 Revised:2023-12-08 Published:2023-12-28
  • Contact: E-mail: lvll800@126.com; xswang@jsnu.edu.cn
  • Supported by:
    Higher Education Program in Jiangsu Province(22KJD150003); 2023 Jiangsu Normal University Laboratory Research Project(L2023YB08)

2-Methylene-2,3-dihydrobenzofuran derivatives, as one of the core skeletons of various natural products and drugs, are of great significance in finding new methods for effectively synthesizing 2-methylene-2,3-dihydrobenzofuran from easily available raw materials. Herein, a novel silver-catalyzed 5-exo-dig cyclization reaction of orth-hydroxyphenyl alkynyl alcohols has been developed, providing an efficient and modular method for the construction of 2-methylene-2,3-dihydrobenzofuran. Featuring the advantages of mild conditions, simple operation, and high efficiency, the reaction requires the utilization of 2 mol% of silver carbonate as a catalyst and 5 mol% of isocyanide as a ligand at room temperature.

Key words: silver, isocyanide, cyclization, propargylic alcohol, benzofuran