Bu4N+X-(OAc)2 Assisted Oxidation and Halogenation of Anilines

Hengchang      Ma; Jinxia      Wang; Ning      An; Wenfeng      Li; Lianhua      Bai; Xiaojie      Jia; Ziqiang      Lei

doi:10.2174/157017812801264728

Abstract

The collaborating partners of DMP and quaternary ammonium salt (TBAF, TBAC, TBAB, TBAI) emerged as powerful oxidation and halogenation reagents in the synthesis of structurally diversified iminoquinones were extensively investigated. The plausible mechanism concerned that the in-situ formed Bu4N⁺X^-(OAc)2 was the key intermediate, and further halogenation reaction occurred via electrophilic substitution process.

Keywords: Anilines, DMP, halogenations, oxidation, TBAB, iminoquinone, amino, pharmaceuticals, bromide, ammonium

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Letters in Organic Chemistry

Title:Bu4N⁺X^-(OAc)2 Assisted Oxidation and Halogenation of Anilines

Volume: 9 Issue: 5

Author(s): Hengchang Ma, Jinxia Wang, Ning An, Wenfeng Li, Lianhua Bai, Xiaojie Jia and Ziqiang Lei

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Keywords: Anilines, DMP, halogenations, oxidation, TBAB, iminoquinone, amino, pharmaceuticals, bromide, ammonium

Abstract: The collaborating partners of DMP and quaternary ammonium salt (TBAF, TBAC, TBAB, TBAI) emerged as powerful oxidation and halogenation reagents in the synthesis of structurally diversified iminoquinones were extensively investigated. The plausible mechanism concerned that the in-situ formed Bu4N⁺X^-(OAc)2 was the key intermediate, and further halogenation reaction occurred via electrophilic substitution process.

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Ma Hengchang, Wang Jinxia, An Ning, Li Wenfeng, Bai Lianhua, Jia Xiaojie and Lei Ziqiang, Bu4N⁺X^-(OAc)2 Assisted Oxidation and Halogenation of Anilines, Letters in Organic Chemistry 2012; 9 (5) . https://dx.doi.org/10.2174/157017812801264728