The Cascade Reaction Of 2-Trifluoroacetylphenol With Actived Triplebond Compounds

Organofluorine chemistry as an important part of organic chemistry is one of the fast developing field in the past decade. Own to the Strong electronic withdrawing activity, the fluoroine element can transform the physical and chemical as well as bioactivity proprieties. Organofluorine compounds were applied in many fields including medical, pesticide, dyestuff, and photoelectric material.Chromene and xanthene can be found in many nature products and medical compounds. Most of these compounds are proved to have bioactivities. Espetially, the fluoroine compounds that bearing quaternary stereocenter are important for the medical chemistry. The Chromene and the Xanthene that bearing a trifluoromethylated tetrasubstituted carbon center may have the ability to applied in medical chemistry. Thus, the enantioselective synthesis of Chromene that bearing a quaternary stereo center is of necessity. The contents are as follows.1 The enantioselective synthesis of Chromene that bearing a trifluoromethylated tetrasubstituted carbon center. According to the references we have synthesized 8 2-trifluoroacetylphenols and 15 alkynals as well as the chiral catalysts. Next, we optimized the reaction conditions. We have synthesised 22 Chromenes which are appered to be new compounds determined by NMR, IR, HRMS in the optimized reaction conditions. The absolute configuration determined by X-ray crystal is R. The DFT calculation indicates that the steric factor of alkynal plays a crucial role in determining the stereoselectivity of the reaction. According to references, we also proposed the mechanism.2 The research focused on the the cascade reaction of 2-trifluoroacetylphenol with the benzyne. We optimized the reaction conditions, with the optimized reaction conditions in hand we have synthesised 15 xanthenes that bearing a quaternary stereo center. The NMR, HRMS determined the compounds. According to references, we also proposed the mechanism.3 We attempt to enantioselectively synthetise the Quinolines that bearing a trifluoromethylated tetrasubstituted carbon center. Our work focused on optimization of the reaction conditions, but, unfortunately, the classic reaction conditions didn’t be found.In all, we use the 2-trifluoroacetylphenol enantioselectively to synthetise Chromene as well as the xanthene containing a trifluoromethylated tetrasubstituted carbon center. We developed the methodology to synthetise trifluoromethylated tetrasubstituted carbon center, which is in favour of material and Pharmaceutical Chemistry.