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Halogen-Exchange Fluorination of Aromatic Halides with HF or HF-Base

芳香族卤化物与 HF 或 HF 基的卤素交换氟化

基本信息

批准号：
04650747
负责人：
FUKUHARA Tsuyoshi
金额：
$ 1.22万
依托单位：
Hokkaido University
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1992
资助国家：
日本
起止时间：
1992 至 1993
项目状态：
已结题

项目摘要

Heteroaromatic halides such as chloropyrimidines and halopyridines, chloroquinolines, 2-chlorobenzoxazole, 2-chlorobenzothiazole, or aromatic halides such as 2,4-dinitrochlorobenzene under went halogen-exchange fluorination with the treatement of HF or HF-base solutions to afford the corresponding fluorides in good yields. The reaction may be well explained to start by its initial protonation of nitrogen atom in the substrates. However, the addition of pyridine to HF was not effective for the halogen-exchange fluorination of 2-chloropyrimidine. On the contrary, increasing the amount of pyridine in HF hinders remarkably the halogen-exchange fluorination to be recovered by the substrate 2-chloropyrimidine almost exclusively. The reaction of substituted 2-chloropyridines and chloroquinolines also initiates the exchange fluorination of halogens with HF, which exist adjacent to N atom in the ring, affording the corresponding fluoride, in good yields.

氯代嘧啶和卤代吡啶等杂芳族卤化物、氯喹啉、2-氯苯并恶唑、2-氯苯并噻唑或2，4-二硝基氯苯等芳香族卤化物在HF或HF碱溶液中进行卤素交换氟化反应，以较高的产率得到相应的氟化物。该反应可以很好地解释为从底物中氮原子的初始质子化开始。但是，在氟化氢中加入吡啶对2-氯嘧啶的卤素交换氟化反应不起作用。反之，随着氟化氢中吡啶含量的增加，卤素交换氟化反应几乎完全被底物2-氯嘧啶所恢复。取代的2-氯吡啶和氯喹啉的反应还引发卤素与氟化氢的交换氟化，氟化氢存在于环中N原子附近，以良好的产率提供相应的氟化物。