801289-32-7Relevant academic research and scientific papers
Base-Controlled Regiodivergent Azidation of Trifluoromethyl Alkenyl Triflates: Transition-Metal-Free Access to CF3-Containing Allyl Azides and Alkenyl Azides
Zhao, Yilong,Zhou, Yuhan,Zhang, Chunxia,Li, Dong,Sun, Puhua,Li, Jianzhe,Wang, Huan,Liu, Jianhui,Qu, Jingping
, p. 2858 - 2868 (2018/03/09)
A base-controlled regiodivergent azidation of trifluoromethyl alkenyl triflates providing either (E)-3-azido-1-aryl-4,4,4-trifluorobut-1-ene (CF3-containing allyl azides) or (Z)-1-azido-1-aryl-4,4,4-trifluorobut-1-ene (CF3-containing alkenyl azides) is described. Catalyzed by Et3N, the azidation of trifluoromethyl alkenyl triflates with TMSN3 gave CF3-containing allyl azides. On the other hand, using stoichiometric DBU, the regioisomeric azidation products, CF3-containing alkenyl azides, were obtained in good yield. A further transformation for CF3-containing amines, triazoles, and azirines highlights the practical applicability of this transition-metal-free protocol.
Synthesis of β-Trifluoromethylated Ketones from Propargylic Alcohols by Visible Light Photoredox Catalysis
Park, Sehyun,Joo, Jung Min,Cho, Eun Jin
, p. 4093 - 4097 (2015/07/01)
Regioselective trifluoromethylation at a remote position represents an important challenge in the development of biologically active molecules and functional materials. A practical method to access β-trifluoromethyl ketones from readily available propargylic alcohols by visible light photocatalysis has been developed. Trifluoromethylation of propargylic alcohols with CF3I in the presence of Ru(bpy)3Cl2 as the photocatalyst followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product. β-Trifluoromethyl ketones are synthesized from readily available propargylic alcohols by visible light photocatalysis. Trifluoromethylation followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product.
Facile one-pot preparation of allylic alcohols with a fluorine-containing alkyl group at the γ-position
Yamazaki, Takashi,Ichikawa, Masashi,Kawasaki-Takasuka, Tomoko,Yamada, Shigeyuki
, p. 151 - 154 (2013/10/01)
A useful one-pot preparation method of allylic alcohols with fluorinated alkyl groups at the γ position was developed from the corresponding enoates by way of the DIBAL-mediated half reduction, followed by nucleophilic attack of Grignard reagents to aldehydes equilibrating with aluminium acetals.
Electronically promoted Payne rearrangement of 3-CF3-2,3- epoxyalcohols
Yamazaki, Takashi,Ichige, Tatsuro,Kitazume, Tomoya
, p. 4073 - 4076 (2007/10/03)
(Chemical Equation Presented) Smooth and selective Payne rearrangement was achieved for the above types of epoxyalcohols with a CF3 group so as to form thermodynamically more stable alkoxides, where the strongly electron-withdrawing nature of this moiety played a significantly important role and was proved to overcome increased steric instability of epoxides from syn-E to anti-Z isomers.
