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Synfacts 2024; 20(08): 0843
DOI: 10.1055/s-0043-1774942
Polymer-Supported Synthesis

Hydrogenolysis of C–O Bonds in Alcohols, Carbonyls, and Ethers Using Pt NPs Supported on Al(PO3)3

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Oshida K, Yuan K, Yamazaki Y, Tsukimura R, Nishio H, Nomoto K, Miura H, Shishido T, Jin X, *, Nozaki K. * The University of Tokyo, Japan
Hydrogen-Induced Formation of Surface Acid Sites on Pt/Al(PO3)3 Enables Remarkably Efficient Hydrogenolysis of C–O Bonds in Alcohols and Ethers.

Angew. Chem. Int. Ed. 2024;
63: e202403092
DOI: 10.1002/anie.202403092.
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Key words

platinum catalysis - Brønsted acid - hydrogenolysis - C–O bond cleavage - alcohols - ketones - aldehydes - ethers

Significance

Platinum nanoparticles supported on Al(PO3)3 (Pt/Al(PO3)3 ), prepared according to equation 1, catalyzed the hydrogenolysis of C–O bonds in alcohols and carbonyls under 1 atm H2 or Ar/H2 (9:1) atmosphere to afford the corresponding hydrocarbons in up to >99% yield (eq. 2). Pt/Al(PO3)3 also promoted the hydrogenolysis of ethers under similar conditions to afford the corresponding hydrocarbons and alcohols in up to 95% yield (eq. 3).


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Comment

The exhaustive hydrogenation of a biomass derived furanic compound took place at 110 °C with Pt/Al(PO3)3 to give 6-propylundecane, a green fuel, in 87% GC yield (eq. 4). In the hydrogenolysis of 4-ethylbenzyl alcohol, the catalyst was recovered and reused four times without significant loss of its catalytic activity. Mechanistic studies suggested that Brønsted acid sites on the catalyst surface is essential to activate the C–O bond.


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Publication History

Article published online:
25 July 2024

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