American Chemical Society
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Divergent Synthesis of Fluorinated Alkenes, Allenes, and Enynes via Reaction of 2‑Trifluoromethyl-1,3-enynes with Carbon Nucleophiles

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journal contribution
posted on 2022-10-31, 13:34 authored by Juan Zhang, Zhi-Guang Ma, Yu Tian, Wei Li, Wen-Chao Gao, Hong-Hong Chang
Herein, inorganic base K3PO4 promoted divergent synthesis of CF3-substituted allenes, cyclopentenes, alkynes, and fluorinated enynes via regioselective nucleophilic addition of carbon nucleophiles to 2-trifluoromethyl-1,3-enynes was developed. With the choice of different carbon nucleophiles, various fluorinated compounds could be obtained under K3PO4/DMF reaction system. When malononitriles were used as nucleophiles, CF3-substituted allenes, cyclopentenes, and alkynes could be obtained, respectively. By using 1,3-dicarbonyl compounds as nucleophiles, ring-monofluorinated 4H-pyrans could be prepared, and 1,1-difluoro-1,3-enynes could be furnished with the participation of diethyl malonate. Moreover, these five kinds of fluorinated allenes, alkenes, and enynes are valuable building blocks.