Trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper
2002
Abstract
A literature method reported for the prepn. of trifluoromethyl substituted benzenes from iodobenzene and congeners was successfully extended to the pyridine series. 2-Iodopyridines can be converted into 2-(trifluoromethyl)pyridines almost quant. by displacement of iodide by (trifluormethyl)copper generated in situ from (trifluoromethyl)trimethylsilane in the presence of cuprous iodide and potassium fluoride. In contrast, yields are moderate at best if 3- and 4-iodopyridines or 2-bromopyridines are used as the starting materials. [on SciFinder (R)]
Details
Title
Trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper
Author(s)
Cottet, Fabrice ; Schlosser, Manfred
Published in
European Journal of Organic Chemistry
Issue
2
Pages
327-330
Date
2002
Keywords
Halomethylation (trifluoromethylation; prepn. of trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper); trifluoromethyl substituted pyridine prepn; pyridine trifluoromethyl substituted prepn; coupling reaction trifluoromethylcopper trifluoromethyl pyridine prepn; halomethylation trifluoromethylation pyridine halide
Note
CAN 137:33189 27-16 Heterocyclic Compounds (One Hetero Atom) Section de Chimie (BCh),Universite Lausanne,Lausanne,Switz. Journal 1434-193X written in English. 624-28-2 (2,5-Dibromopyridine); 625-92-3 (3,5-Dibromopyridine); 626-05-1 (Pyridine, 2,6-dibromo); 1120-90-7 (3-Iodopyridine); 5029-67-4 (2-Iodopyridine); 15854-87-2 (4-Iodopyridine); 73290-22-9 (Pyridine, 2-bromo-5-iodo); 75806-85-8 (2,3,5-Tribromopyridine); 78607-36-0 (Pyridine, 2-chloro-3-iodo); 153034-86-7 (Pyridine, 2-chloro-4-iodo); 223463-13-6 (Pyridine, 5-bromo-2-iodo); 233770-01-9 (Pyridine, 3-bromo-5-iodo); 234111-08-1 (Pyridine, 2-bromo, 6-iodo) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper); 5140-72-7P (Pyridine, 2-bromo, 6-chloro); 258506-66-0P (Pyridine, 2-chloro, 6-iodo); 436799-34-7P; 436799-35-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper); 7681-65-4 (Copper iodide (CuI); 7789-23-3 (Potassium fluoride (KF); 81290-20-2 ((Trifluoromethyl)trimethylsilane) Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper); 368-48-9P (2-Pyridinetrifluoromethyl); 3796-23-4P (3-Pyridinetrifluoromethyl); 3796-24-5P (4-Pyridinetrifluoromethyl); 39890-95-4P (Pyridine, 2-chloro-6-trifluoromethyl); 50488-42-1P (Pyridine, 2-bromo-5-(trifluoromethyl); 65753-47-1P (Pyridine, 2-chloro-3-(trifluoromethyl); 81565-18-6P (Pyridine, 2-chloro-4-(trifluoromethyl); 189278-27-1P (Pyridine, 2-bromo-6-trifluoromethyl); 436799-32-5P; 436799-33-6P; 436799-36-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of trifluoromethyl-substituted pyridines through displacement of iodine by in situ generated (trifluoromethyl)copper)
Laboratories
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
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Peer-reviewed publications
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Record creation date
2006-03-03