Access to Difluoromethylated Alkynes through the Castro-Stephens Reaction

被引：18
作者：
Besset, Tatiana [1 ,2 ,3 ,4 ,5 ]
Poisson, Thomas [1 ,2 ,3 ,4 ,5 ]
Pannecoucke, Xavier [1 ,2 ,3 ,4 ,5 ]
机构：
[1] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France
[2] Normandie Univ, FR 3038, F-76821 Mont St Aignan, France
[3] Univ Rouen, F-76821 Mont St Aignan, France
[4] INSA Rouen, F-76821 Mont St Aignan, France
[5] CNRS, F-76821 Mont St Aignan, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 32期
关键词：
Synthetic methods; Fluorine; Alkynes; Copper; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; FLUOROALKYL IODIDES; CATALYZED TRIFLUOROMETHYLATION; STRAIGHTFORWARD ACCESS; REFORMATSKY REACTION; TERMINAL ALKYNES; ARYL IODIDES; COPPER; FLUORINE; DIFLUOROACETYLATION;
D O I：
10.1002/ejoc.201402937
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of difluoromethylated alkynes is described. A panel of readily available Cu-I acetylides undergo direct difluoromethylation by using BrCF2CO2Et, which is an inexpensive, easy to handle, commercially available fluorinated reagent. The reaction, which is based on a Castro-Stephens transformation, proceeds smoothly under mild conditions offering a new synthetic route for the direct introduction of the difluoromethylated group into alkynes that does not involve ozone-depleting reagents. The resulting products were obtained with good yields by using CsOPiv and Cu(OAc)(2) as additives.
引用
收藏
页码：7220 / 7225
页数：6
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