4.8 Article

Electrophilic Reaction of 2,2,2-Trifluorodiazoethane with the in Situ Generated N-Heterocyclic Carbenes: Access to N-Aminoguanidines

Journal

ORGANIC LETTERS
Volume 18, Issue 17, Pages 4170-4173

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01191

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Funding

  1. National Natural Science Foundation of China [21225208, 21472137, 21532008]
  2. National Basic Research Program of China (973 Program) [2014CB745100]
  3. Tianjin Municipal Science & Technology Commission [14JCZDJC33400]

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A facile and efficient electrophilic reaction of 2,2,2-trifluorodiazoethane (CF3CHN2) with the in situ generated N-heterocyclic carbenes is reported. Under basic conditions, a series of trifluoromethylated N-aminoguanidines were obtained in good to high yields. Furthermore, this protocol was applied in the synthesis of the agrochemical Imidacloprid analogue.

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