Details

Autor(en) / Beteiligte

• Marsh, Thomas G. F.
• Santambrogio, Alessia
• Murray, Ben J.
• Boulton, Lee T.
• Aguilar, Juan A.
• Yufit, Dmitry S.
• Sandford, Graham
• Brittain, William D. G.

Titel

HFO‐1234yf as a CF 3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

Ist Teil von

• European journal of organic chemistry, 2023-03, Vol.26 (11)

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Abstract Trifluoromethyl ynones derived from the refrigerant gas HFO‐1234yf (2,3,3,3‐tetrafluoropropene) react with nucleophiles via a Michael‐type addition process and the allenolate intermediate formed reacts intramolecularly with a carbonyl group to form heterocyclic derivatives. Thus, reaction of 2‐amino and 2‐hydroxyl benzaldehyde or ketone substrates with trifluoromethyl ynone derivatives gives trifluoromethyl quinoline and chromene products by a one‐pot tandem ring closing sequence, forming pharmaceutically relevant structures from an inexpensive starting material without the need for transition metals or column chromatography. The 2‐trifluoromethylquinoline products also show unusual fluxional behaviour, which was explored through 2‐D NMR and X‐ray crystallographic studies.