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Synfacts 2023; 19(06): 0591
DOI: 10.1055/s-0042-1752697
Polymer-Supported Synthesis

Oxidative [3+2] Cycloaddition of Phenols with Styrenes Using a Photocatalytic COF

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Parvatkar PT, Kandambeth S, Shaikh AC, Nadinov I, Yin J, Kale VS, Healing G, Emwas A.-H, Shekhah O, Alshareef HN, Mohammed OF, Eddaoudi M. * King Abdullah University of Science and Technology (KAUST), Thuwal, Kingdom of Saudi Arabia
A Tailored COF for Visible-Light Photosynthesis of 2,3-Dihydrobenzofurans.

J. Am. Chem. Soc. 2023;
145: 5074-5082
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Key words

covalent organic frameworks - photocatalysis - [3+2] cycloaddition - 2,3-dihydrobenzofurans

Significance

A covalent organic framework containing hexaazatriphenylene and phenazine units (Hex-Aza-COF) catalyzed the oxidative [3+2] cyclo­addition of phenols and styrenes in the presence of (NH4)2S2O8 under white LEDs irradiation to afford the corresponding 2-aryl-2,3-dihydrobenzofurans in up to 95% yield (eq. 1).


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Comment

In the oxidative [3+2] cycloaddition of 4-methoxyphenol and trans-p-methoxypropenylbenzene, Hexa-Aza-COF was recovered by centrifugation and reused four times without significant loss of its catalytic activity. The authors have previously reported the preparation of Hex-Aza-COF and its application as an electrode (Adv. Energy Mater. 2020, 10, 2001673; ACS Energy Lett. 2020, 5, 2256).


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Publication History

Article published online:
11 May 2023

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