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,Organic Letters

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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
Organic Letters ( IF 4.9 ) Pub Date : 2016-01-21 00:00:00 , DOI: 10.1021/acs.orglett.5b03448
Mingzhu Zhao ₁ , Ling Ming ₁ , Jialiang Tang ₁ , Xiaoming Zhao ₁

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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.

中文翻译：

湿式四正丁基铵氟化物对1-（2,2-二溴乙烯基）苯衍生物的区域选择性氟化：（Z）-1-（2-溴-1-氟乙烯基）苯的一锅法合成

使用湿式四正丁基氟化铵（TBAF·3H ₂ O）作为甲苯中的碱或氟源，对1-（2,2-二溴乙烯基）苯衍生物进行直接氟化，得到（Z）-1 -（2-溴-1-氟乙烯基）苯化合物的最高区域选择性可达81％。该反应结果在很大程度上取决于反应条件。还研究了该反应的机理。

更新日期：2016-01-21

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