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Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions.

ABSTRACT: For the selective synthesis of N-cyano sulfilimines, we have developed a new method based on the soft-soft interaction between thionium ion electrophiles and cyanonitrene nucleophiles. The stable thionium ion was successfully obtained by oxidative dearomatization using phenyliodine (III) diacetate (PIDA) in N,N-dimethylformamide (DMF). The sulfur imination reactions were tolerant to a wide range of functional groups and exhibited high selectivities and excellent yields. The existence of thionium ion intermediates was confirmed by ultraviolet/visible (UV/vis) spectroscopy and 1H NMR experiments.

SUBMITTER: Kim SM

PROVIDER: S-EPMC7203956 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions.

Kim Sang Mee SM Kang On-Yu OY Lim Hwan Jung HJ Park Seong Jun SJ

ACS omega 20200422 17

For the selective synthesis of N-cyano sulfilimines, we have developed a new method based on the soft-soft interaction between thionium ion electrophiles and cyanonitrene nucleophiles. The stable thionium ion was successfully obtained by oxidative dearomatization using phenyliodine (III) diacetate (PIDA) in N,N-dimethylformamide (DMF). The sulfur imination reactions were tolerant to a wide range of functional groups and exhibited high selectivities and excellent yields. The ...[more]

PMID: 32391507

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