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使用异丙基氯化镁-双[2-(N,N-二甲基氨基)乙基]醚配合物对带有敏感官能团的芳基卤化物进行非低温碘/溴-镁交换反应。

Noncryogenic I/Br-Mg exchange of aromatic halides bearing sensitive functional groups using i-PrMgCl-bis[2-(N,N-dimethylamino)ethyl] ether complexes.

作者信息

Wang Xiao-Jun, Sun Xiufeng, Zhang Li, Xu Yibo, Krishnamurthy Dhileepkumar, Senanayake Chris H

机构信息

Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA.

出版信息

Org Lett. 2006 Jan 19;8(2):305-7. doi: 10.1021/ol052704p.

Abstract

[reaction: see text] Iodo- and bromoaromatics bearing sensitive carboxylic ester and cyano groups underwent a selective halide-magnesium exchange with isopropylmagnesium chloride at ambient temperature in the presence of bis[2-(N,N-dimethylamino)ethyl] ether to afford the corresponding Grignard reagents. The newly formed reactive Grignard reagents were allowed to react with electrophiles such as trimethylborate to afford arylboronic acids in good to excellent yields.

摘要

[反应:见正文] 带有敏感羧酸酯和氰基的碘代和溴代芳烃在双[2-(N,N-二甲基氨基)乙基]醚存在下,于室温下与异丙基氯化镁进行选择性卤化物-镁交换,得到相应的格氏试剂。使新形成的活性格氏试剂与诸如硼酸三甲酯等亲电试剂反应,以良好至优异的产率得到芳基硼酸。

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