Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

• Takashi Yamazaki,
• Yoh Nakajima,
• Minato Iida and
• Tomoko Kawasaki-Takasuka

Beilstein J. Org. Chem. 2021, 17, 132–138, doi:10.3762/bjoc.17.14

• ; salicylate derivatives; Introduction It is well known that the incorporation of a fluorine atom or a fluorine-containing group into organic compounds sometimes affects their original biological activities [1][2][3], and thus the development of methods for the construction of such molecules with this atom or

• Sandford group clarified the high potency of these compounds for the conjugate addition of N- as well as O-nucleophiles [21]. On the basis of such an idea, we tried two routes to gain access to 1) 4-substituted 6-(trifluoromethyl)salicylate derivatives (C-nucleophiles) and 2) 6-substituted 4

• obtained in good to excellent yield without contamination by the deacetylated products 5. With the success of the regiospecific formation of 4-substituted 6-(trifluoromethyl)salicylate derivatives 4, as shown in Table 4, the application of ynones 2 was demonstrated at the next stage for the construction of