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Synfacts 2023; 19(04): 0383
DOI: 10.1055/s-0042-1752629
Polymer-Supported Synthesis

Semi-Hydrogenation of Alkynes and Suzuki Coupling with a Polyurethane Foam-Supported Pd Catalyst

Contributor(s):
Yasuhiro Uozumi
,
Shintaro Okumura
Peng H, Zhang X, Papaefthimiou V, Pham-Huu C, *, Ritleng V. * Université de Strasbourg, France
Pd-Functionalized Polydopamine-Coated Polyurethane Foam: A Readily Prepared and Highly Reusable Structured Catalyst for Selective Alkyne Semi-Hydrogenation and Suzuki Coupling under Air.

Green Chem. 2023;
25: 264-279
DOI: 10.1039/d2gc03283j.
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Key words

polyurethane - polydopamine - palladium catalysis - semi-hydrogenation - Suzuki coupling

Significance

A novel polymeric Pd catalyst, Pd-functionalized polydopamine-coated polyurethane foam (Pd@PDA@PUF), was readily prepared from polyurethane (PUF) through immersing-rinsing processes with dopamine and PdCl2(NH3)4. Pd@PDA@PUF catalyzed the semi-hydrogenation of terminal as well as internal alkynes with excellent alkene selectivity. Pd@PDA@PUF also promoted the Suzuki–Miyaura bialyl coupling efficiently under air.


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Comment

Pd@PDA@PUF was readily recovered and reused without significant loss of its catalytic performance. A single cubic sample of Pd@PDA@PUF (8 cm3; Pd loading 7 μmol) catalyzed 15 consecutive catalytic reactions consisting five runs of semi-hydrogenation of phenylacetylene, five runs of Suzuki coupling of PhBr and PhB(OH)2, and again five runs of semi-hydrogenation of phenylacetylene; 0.23 mol% Pd for all reactions with 3 mmol of substrate in each run.


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Publication History

Article published online:
17 March 2023

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