Synfacts 2018; 14(01): 0095
DOI: 10.1055/s-0036-1591031
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Cross-Coupling Mediated by Polymer-Supported Siloxanes

Yasuhiro Uozumi
Takuma Sato
Nguyen MH. O’Brien KT. Smith III AB. * University of Pennsylvania, Philadelphia, USA
Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents.

J. Org. Chem. 2017;
82: 11056-11071
Further Information

Publication History

Publication Date:
15 December 2017 (online)



Polymer-supported siloxanes were developed as transfer agents for cross-coupling reactions involving organolithium reagents. For example, the polystyrene-supported siloxane 1 was treated with an aryl or alkenyl lithium 2, and the resulting material was treated with an aryl halide 3 in the presence of PdCl2, CuI, and ligand L to give the corresponding product 4 in 68–97% yield.



The transfer agent 1 was recovered almost quantitatively by simple filtration and rinsing, and reused in the cross-coupling several times. No cross-contamination of the products 4 was detected in a series of ten reactions with recycled 1 and various combinations of organolithium ­reagents 2 and aryl halides 3.