Regioselective Fluorination of 1-(2,2-Dibromovinyl)benzene Derivatives with Wet Tetra-n-butylammonium Fluoride: One-Pot Synthesis of (Z)-1-(2-Bromo-1-fluorovinyl)benzenes

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• 作者：Mingzhu Zhao ; Ling Ming ; Jialiang Tang ; Xiaoming Zhao
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：416-419
• 全文大小：317K
• ISSN：1523-7052

文摘

A direct fluorination of 1-(2,2-dibromovinyl)benzene derivatives using wet tetra-n-butylammonium fluoride (TBAF·3H₂O) as either a base or a fluorine source in toluene was accomplished, which provided (Z)-1-(2-bromo-1-fluorovinyl)benzene compounds in up to 81% yields with high regioselectivities. This reaction results strongly depend upon the reaction conditions. The mechanism of this reaction was investigated as well.