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Copper‐Catalyzed Synthesis of α‐Trifluoromethylacrylates from Trifluoroborylacrylates via Stereoretentive Radical Trifluoromethylation
Author(s) -
Jos Swetha,
Santos Webster L.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000937
Subject(s) - chemistry , trifluoromethylation , reagent , yield (engineering) , diastereomer , catalysis , substrate (aquarium) , pyran , combinatorial chemistry , copper , radical , organic chemistry , medicinal chemistry , trifluoromethyl , alkyl , materials science , oceanography , metallurgy , geology
We report the synthesis of α‐trifluoromethylacrylates from α‐trifluoroborylacrylates via a stereoretentive radical trifluoromethylation with inexpensive reagents NaSO 2 CF 3 and TBHP at room temperature. Under these conditions, a wide substrate scope afforded the ( E )‐diastereomer exclusively in moderate to good yield. The utility of the reaction products is demonstrated in the synthesis of phenyl‐4 H ‐pyran, a potent and selective class of IKCa channel blockers.