Ou W,
Zhang G,
Wu J,
Su C.
* Shenzhen University, P. R. of China and National University of Singapore, Singapore
Photocatalytic Cascade Radical Cyclization Approach to Bioactive Indoline-Alkaloids
over Donor–Acceptor Type Conjugated Microporous Polymer.
ACS Catal. 2019;
9: 5178-5183
Key words
photocatalysis - formyloxindoles - formylarylation - arylacrylamides - indoline alkaloids
- microporous polymers
Significance
A carbazolic-cyano conjugated microporous polymer (CC-MNP), prepared according to
equation 1, catalyzed the 1,2-formylarylation of N-arylacrylamides with 1,3-dioxolane in the presence of TBHP under irradiation by a
5 W blue LED to give the corresponding formyl-substituted oxindoles in ≤81% yield
(eq. 2). CC-MNP also catalyzed a gram-scale synthesis of 2-(5-methoxy-1,3-dimethyl-2-oxoindolin-3-yl)acetaldehyde
(76% yield, 1.77 g).
Comment
CC-MNP was characterized by means of SEM, UV/Vis-NIR, FT-IR, and TGA analyses. In
the 1,2-formylarylation of N-methyl-N-phenylmethacrylamide, the catalyst was reused four times with no significant loss
of its catalytic activity (first run: 81% yield, fifth run: 75% yield).
