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Synfacts 2019; 15(09): 1035
DOI: 10.1055/s-0039-1690175
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Photocatalytic 1,2-Formylarylation of N-Arylacrylamides

Contributor(s):
Yasuhiro Uozumi
,
Ryoko Niimi
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
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Further Information

Publication History

Publication Date:
20 August 2019 (online)

 
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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).


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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).


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