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Synfacts 2021; 17(01): 0067
DOI: 10.1055/s-0040-1706613
Polymer-Supported Synthesis

Titania-Promoted Hydroalkylation of Electron-Deficient Olefins

Contributor(s):
Yasuhiro Uozumi
,
Shintaro Okumura
Zhu Q, Nocera DG. * Harvard University, Cambridge, USA
Photocatalytic Hydromethylation and Hydroalkylation of Olefins Enabled by Titanium Dioxide Mediated Decarboxylation.

J. Am. Chem. Soc. 2020;
142: 17913-17918
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Key words

titanium dioxide catalysis - photocatalysis - hydroalkylation - alkenes

Significance

Commercially available anatase TiO2 nanoparticles promoted the hydroalkylation of alkenes bearing electron-withdrawing groups with carboxylic acids under 390 nm light irradiation to give the corresponding hydrocarbons in up to 91% yield (eq. 1).


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Comment

Mechanistic studies indicated that alkyl radicals were generated by decarboxylation of the carboxylic acids promoted by TiO2 (eq. 2). The catalytic activity of TiO2 was superior to that of various heterogeneous semiconducting photocatalysts such as ZnO, WO3, or CdS.


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Publication History

Article published online:
16 December 2020

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