Palladium-catalyzed Cycloaddition of Aryl Silylethynyl Ethers with Isocyanates via <i>o</i>-C–H Cleavage

• Yasunori Minami

  Research and Development Initiative, Chuo University

• Mayuko Kanda

  Department of Applied Chemistry, Chuo University

• Tamejiro Hiyama

  Research and Development Initiative, Chuo University

Abstract

Palladium-catalyzed cycloaddition of alkynyl aryl ethers with isocyanates proceeds through o-C–H activation to afford 2-methylidene-2H-1,4-benzoxazin-3(4H)-one derivatives. Deuterium-labeling experiment shows that o-hydrogen is cleaved selectively and migrated to 2-methylidene moiety in the product. Various substrates are applied to this transformation to afford various substituted cycloadducts. 1,4-Bis(alkynoxy)benzenes can be used for the synthesis of multicondensed cycles to afford benzo[1,2-b:4,5-b′]bis[1,4]oxazine-3,8-dione derivatives.

Journal

• Chemistry Letters

  Chemistry Letters 43 (9), 1408-1410, 2014-05-20

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360846644035691136
• NII Article ID: 130004427159
• DOI: 10.1246/cl.140452
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/43/9/1408/55636505/cl.140452.pdf
• Data Source:
  • Crossref
  • CiNii Articles
  • KAKEN