Access to α,α-dihaloacetophenones through anodic C C bond cleavage in enaminones

• Published in: Tetrahedron letters Vol. 88; pp. 153575 - 153581
• Main Authors: Zhang, Zhenlei, Yang, Jiusi, Wu, Kairui, Yu, Renjie, Bu, Jiping, Huang, Zijun, Li, Shaoke, Ma, Xiantao
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 05.01.2022
• Subjects: ambient temperature; anodes; Chemistry; Chemistry, Organic; cleavage (chemistry); electrochemistry; electrosynthesis; Physical Sciences; Science & Technology; SELECTIVE PREPARATION; alpha,alpha-Dihaloacetophenones; AMBIENT; EFFICIENT SYNTHESIS; ALPHA; ALKYNES; ELECTROCHEMICAL SYNTHESIS; KETONES; REDUCTION; Electrosynthesis; N,N-Dimethyl enaminone; Green chemistry; WATER

We have developed a method to synthesize alpha,alpha-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl-2 or Br-2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C=C of the N,N-dimethyl enam...