82203-82-5Relevant academic research and scientific papers
Diverse copper(iii) trifluoromethyl complexes with mono-, bi- and tridentate ligands and their versatile reactivity
Zhang, Song-Lin,Xiao, Chang,Wan, Hai-Xing
supporting information, p. 4779 - 4784 (2018/04/11)
Cu(iii) trifluoromethyl complexes are proposed as essential intermediates for many copper-promoted trifluoromethylation reactions, but remain elusive and scarcely explored. We report herein the isolation and spectroscopic and X-ray crystallographic charac
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.
Copper-mediated trifluoromethylation using phenyl trifluoromethyl sulfoxide
Li, Xinjin,Zhao, Jingwei,Zhang, Liang,Hu, Mingyou,Wang, Limin,Hu, Jinbo
supporting information, p. 298 - 301 (2015/03/04)
A new method for the generation of trifluoromethylcopper ( CuCF3 ) species from readily available phenyl trifluoromethyl sulfoxide has been developed. The CuCF3 reagent can be applied in efficient trifluoromethylations of aryl iodides and activated aryl bromides in the absence of additional ligands. Furthermore, the CuCF3 species can also undergo oxidative cross-coupling with terminal alkynes and arylboronic acids.
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.
Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent Dedicated to Professor Pierre Vogel on the occasion of his 70th birthday
Dubbaka, Srinivas Reddy,Nizalapur, Shashidhar,Atthunuri, Azmi Reddy,Salla, Manohar,Mathew, Thresen
, p. 2118 - 2121 (2014/03/21)
Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates.
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.
Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation of alkynyltrifluoroborates
Zheng, Huidong,Huang, Yuanyuan,Wang, Zhiwei,Li, Huaifeng,Huang, Kuo-Wei,Yuan, Yaofeng,Weng, Zhiqiang
supporting information, p. 6646 - 6649 (2013/01/15)
A new method for the synthesis of trifluoromethylated acetylenes is developed which involves the copper-catalyzed trifluoromethylation of alkynyltrifluoroborates with an electrophilic trifluoromethylating reagent. This method offers significant advantages such as efficiency and mild and base-free reaction conditions. A plausible mechanism is proposed.
Mild copper-catalyzed trifluoromethylation of terminal alkynes using an electrophilic trifluoromethylating reagent
Weng, Zhiqiang,Li, Huaifeng,He, Weiming,Yao, Liang-Feng,Tan, Jianwei,Chen, Jinfa,Yuan, Yaofeng,Huang, Kuo-Wei
supporting information; experimental part, p. 2527 - 2531 (2012/04/23)
A catalytic process for trifluoromethylation of terminal alkynes with Togni's reagent has been developed, affording trifluoromethylated acetylenes in good to excellent yields. The reaction is conducted at room temperature and exhibits tolerance to a range
Sulfoximines as a versatile scaffold for electrophilic fluoroalkylating reagents
Urban, Celine,Cadoret, Frederic,Blazejewski, Jean-Claude,Magnier, Emmanuel
experimental part, p. 4862 - 4867 (2011/10/09)
New electrophilic fluoroalkylating agents based on the sulfoximine skeleton as a common platform are described. We demonstrate the importance of the activating group, attached to the nitrogen, and its specificity for the fluorinated group to be delivered.
Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
Konno, Tsutomu,Chae, Jungha,Kanda, Masashi,Nagai, Go,Tamura, Kazushige,Ishihara, Takashi,Yamanaka, Hiroki
, p. 7571 - 7580 (2007/10/03)
Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2· TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh 3)4, reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields.
