Synthesis of Non‐Terminal Alkenyl Ethers, Alkenyl Sulfides, and N‐Vinylazoles from Arylaldehydes or Diarylketones, DMSO and O, S, N‐Nucleophiles

• Published in: Advanced synthesis & catalysis Vol. 364; no. 8; pp. 1473 - 1480
• Main Authors: Nie, Zhiwen, Lv, Huifang, Yang, Tonglin, Su, Miaodong, Luo, Weiping, Liu, Qiang, Guo, Cancheng
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 12.04.2022; Wiley Subscription Services, Inc
• Subjects: Alkenyl Ethers; Alkenyl Sulfides; Arylaldehydes or Diarylketones; Chemistry; Chemistry, Applied; Chemistry, Organic; DMSO; Ethers; N-Vinylazoles; Nucleophiles; Physical Sciences; Science & Technology; Sulfides; Synthesis; Alkenyl Ethers; Alkenyl Sulfides; ENOL ETHERS; DMSO; EFFICIENT SYNTHESIS; VINYL SULFIDES; HYDROAMINATION; Arylaldehydes or Diarylketones; CALCIUM CARBIDE; INDOLES; CASCADE REACTION; N-Vinylazoles; PALLADIUM-CATALYZED SYNTHESIS; ARYL; STEREOSELECTIVE-SYNTHESIS
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202200020

A transition‐metal‐free protocol for the synthesis of non‐terminal alkenyl ethers, alkenyl sulfides, and N‐vinylazoles from arylaldehydes or diarylketones, DMSO and O, S, N‐nucleophiles has been reported. In this protocol, 24 examples of non‐terminal alkenyl ethers and 28 examples of non‐terminal alkenyl sulfides in 72–95% yields have been synthesized within 5 min. Moreover, 27 examples of non‐terminal N‐vinylazoles with 57–88% yields have also been synthesized within 2 hours. The preliminary mechanism investigations revealed that arylaldehydes or diarylketones offered a carbon atom, DMSO provided a methine and O, S, N‐nucleophiles contributed one X atom for constructing C=C−X structure.