Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 195-203.DOI: 10.6023/cjoc202307019 Previous Articles     Next Articles



李梦竹, 孟博莹, 兰文捷, 傅滨*()   

  1. 中国农业大学理学院 北京 100193
  • 收稿日期:2023-07-19 修回日期:2023-08-28 发布日期:2023-09-21
  • 基金资助:

Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides

Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu()   

  1. College of Science, China Agricultural University, Beijing 100193
  • Received:2023-07-19 Revised:2023-08-28 Published:2023-09-21
  • Contact: *E-mail:
  • Supported by:
    National Key Research and Development Program of China(2017YFD0200301)

A facile and efficient approach to dihydrobenzofurans from sulfur ylides and o-quinone methides (o-QMs) was developed. In most cases, the reaction could be completed in the presence of N,N-diisopropylethylamine (DIPEA) in CH2Cl2 at room temperature within 1 h, providing trans-2,3-disubstitiuted dihydrobenzofurans in good to excellent yields. The reaction could expand to a scale of grams, and the products could be converted into the potentially bioactive benzofuran derivatives. The plausible mechanism is proposed.

Key words: dihydrobenzofuran, o-quinone methides, sulfur ylide, [4+1] cycloaddition, base-catalysis