4.8 Article

One-Pot Cascade Leading to Direct α-Imidation of Ketones by a Combination of N-Bromosuccinimide and 1,8-Diazabicyclo[5.4.1]undec-7-ene

Journal

ORGANIC LETTERS
Volume 14, Issue 16, Pages 4202-4205

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301871s

Keywords

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Funding

  1. National Natural Science Foundation of China [20972027, 21172034]
  2. Program for New Century Excellent Talents in University [NCET-11-0611]
  3. Department of Science and Technology of Jilin Province [201215002]
  4. Fundamental Research Funds for the Central Universities [11SSXT129]
  5. State Key Laboratory of Supramolecular Structure and Materials [sklssm201225]

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A one-pot cascade transformation of ketones into alpha-imidoketones has been developed, in which N-bromosuccinimide (NBS) provides both electrophilic bromine and nucleophilic nitrogen sources, and diazabicyclo[5.4.1]undec-7-ene (DBU) functions as a base and a nucleophilic promoter for the activation of NBS. alpha-Bromination is supposed as the key step in the process, which takes place between more electrophilic bromide active species and enolates.

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