1537898-07-9Relevant academic research and scientific papers
Visible-Light Photoredox-Catalyzed Semipinacol-Type Rearrangement: Trifluoromethylation/Ring Expansion by a Radical-Polar Mechanism
Sahoo, Basudev,Li, Jun-Long,Glorius, Frank
, p. 11577 - 11580 (2015)
A visible-light-mediated photoredox-catalyzed semipinacol-type rearrangement proceeding via 1,2 alkyl migration was developed. In this transformation, trifluoromethylation of the C=C bond of α-(1-hydroxycycloalkyl)-substituted styrene derivatives is followed by ring expansion of the 1-hydroxycycloalkyl group to deliver novel cycloalkanones with all-carbon quaternary centers. The reaction proceeds via a radical-polar mechanism, with trifluoromethylation (radical) and ring expansion (ionic) occurring in the same transformation.
Highly regio- and diastereoselective synthesis of cf3- substituted lactones via photoredox-catalyzed carbolactonization of alkenoic acids
Yasu, Yusuke,Arai, Yusuke,Tomita, Ren,Koike, Takashi,Akita, Munetaka
supporting information, p. 780 - 783 (2014/03/21)
Trifluoromethylative lactonization of both terminal and internal alkenoic acids by photoredox catalysis has been developed. The use of a Ru photocatalyst and Umemoto's reagent as a CF3 source is key in the present carbolactonization. This is the first example of a highly endo- and diastereoselective synthesis of CF3-substituted five-, six-, and seven-membered ring lactones from internal alkenoic acids.
