943-71-5Relevant academic research and scientific papers
Fluoroform-Derived CuCF3 for Trifluoromethylation of Terminal and TMS-Protected Alkynes
He, Lisi,Tsui, Gavin Chit
supporting information, p. 2800 - 2803 (2016/07/06)
An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
Controlled trifluoromethylation reactions of alkynes through visible-light photoredox catalysis
Iqbal, Naeem,Jung, Jaehun,Park, Sehyun,Cho, Eun Jin
supporting information, p. 539 - 542 (2014/01/23)
The control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3-containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF 3I by environmentally benign and efficient visible-light photoredox catalysis. Subtle differences in the combination of catalyst, base, and solvent enabled the control of reactivity and selectivity for the reaction between an alkyne and CF3I. Variety through selectivity: Highly valuable trifluoromethylated alkenyl iodides, alkenes, and alkynes were selectively generated from alkynes and CF3I by environmentally benign and efficient visible-light photoredox catalysis. A suitable choice of catalyst, base, and solvent was crucial for the reactivity and selectivity of these processes.
Practical methods for the synthesis of trifluoromethylated alkynes: Oxidative trifluoromethylation of copper acetylides and alkynes
Tresse, Cedric,Guissart, Celine,Schweizer, Stephane,Bouhoute, Yassine,Chany, Anne-Caroline,Goddard, Mary-Lorene,Blanchard, Nicolas,Evano, Gwilherm
supporting information, p. 2051 - 2060 (2014/07/07)
Two practical and complementary methods are reported for the synthesis of trifluoromethylated alkynes. The first one, a mix-and-stir process, is based on the oxidative trifluoromethylation of readily available and bench-stable copper acetylides while the second one, which displays a broad substrate scope and has several advantages over existing procedures, is based on the oxidative copper-catalyzed direct trifluoromethylation of terminal alkynes. Both reactions provide user-friendly processes for the synthesis of trifluoromethylated acetylenes which can be easily obtained from readily available starting materials.
Direct synthesis of a trifluoromethyl copper reagent from trifluoromethyl ketones: Application to trifluoromethylation
Serizawa, Hiroki,Aikawa, Kohsuke,Mikami, Koichi
supporting information, p. 17692 - 17697 (2014/01/17)
Being economic with fluorine: The direct synthesis of CuCF3 from a cuprate reagent and trifluoromethyl ketones, as one of the most economical and efficient trifluoromethyl sources, was accomplished. The advantages of this method are all of reagents employed are low-cost, operation is simple, and the yield of CuCF3 is virtually quantitative (see scheme). Furthermore, three types of trifluoromethylations smoothly proceeded to provide the corresponding products in high yields. Copyright
