Open AccessOxidative Rearrangement of Stilbenes to 2,2-Diaryl-2-hydroxyacetaldehydes
Author(s) -
Rupali G. Kalshetti,
Chepuri V. Ramana
Publication year - 2020
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.0c03328
Subject(s) - oxidative phosphorylation , chemistry , hydroxylation , iodine , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry , enzyme
A one-pot oxone-mediated/iodine-catalyzed oxidative rearrangement of stilbenes leading to 2,2-diaryl-2-hydroxyacetaldehydes is described. Control experiments revealed that a 2,2-diarylacetaldehyde was initially formed that undergoes subsequent α-hydroxylation. The resulting α-hydroxyaldehydes have been subjected to a one-pot Still-Gennari olefination followed by cyclization, leading to 5,5-diaryl-γ-butenolides.
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