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Recyclable Polystyrene-supported Siloxane-transfer Agent for Palladium-catalyzed Cross-coupling Reactions

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2014 Mar 26
PMID 24661113
Citations 6
Authors
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Abstract

The rational design, synthesis, and validation of a significantly improved insoluble polymer-supported siloxane-transfer agent has been achieved that permits efficient palladium-catalyzed cross-coupling reactions. The cross-linked polystyrene support facilitates product purification with excellent siloxane recycling. Drawbacks of a previous polymer-supported siloxane-transfer agent, relating to reaction efficiency and polymer stability after repeated cycles, have been addressed.

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References
1.
Hornillos V, Giannerini M, Vila C, Fananas-Mastral M, Feringa B . Catalytic direct cross-coupling of organolithium compounds with aryl chlorides. Org Lett. 2013; 15(19):5114-7. DOI: 10.1021/ol402408v. View

2.
Nguyen M, Smith 3rd A . Polymer-supported siloxane transfer agents for Pd-catalyzed cross-coupling reactions. Org Lett. 2013; 15(16):4258-61. PMC: 3771667. DOI: 10.1021/ol402047d. View

3.
Nakao Y, Imanaka H, Sahoo A, Yada A, Hiyama T . Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: an entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction. J Am Chem Soc. 2005; 127(19):6952-3. DOI: 10.1021/ja051281j. View

4.
Nakao Y, Takeda M, Matsumoto T, Hiyama T . Cross-coupling reactions through the intramolecular activation of alkyl(triorgano)silanes. Angew Chem Int Ed Engl. 2010; 49(26):4447-50. DOI: 10.1002/anie.201000816. View

5.
Toy P, Reger T, Garibay P, Garno J, Malikayil J, Liu G . Polytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis. J Comb Chem. 2001; 3(1):117-24. DOI: 10.1021/cc000083f. View