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

Abstract

The concise preparation of 4,4,4-trifluorobut-2-yn-1-ones by the oxidation of the readily accessible corresponding propargylic alcohols as well as their utilization as Michael acceptors for the construction of aromatic and heteroaromatic compounds are reported.

Synthesis of Functionalized Pyrimidines from Propargylic alcohols and their Derivatives: Two Decades of Developments

“…In the year 2021, the concise preparation of 4,4,4‐trifluorobut‐2‐yn‐1‐ones 20 by the oxidation of corresponding sec ‐propargylic alcohols 21 and their utilization as Michael acceptors for the construction of aromatic and heteroatomic compounds including the trifluoromethyl‐pyrimidines 22 , was demonstrated by the research group of Yamazaki (Scheme 11). [21] These ynones 20 have inherent instability on silica gel showing decomposition and hence their reported yields were determined by 19 F‐NMR spectroscopy. The crude reaction mixture of 20 proved to be sufficiently pure and highly potent as Michael acceptor and was further utilized without purification.…”