Synfacts 2016; 12(4): 0397
DOI: 10.1055/s-0035-1561806
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Palladium Cross-Couplings with a Silicon-Based Transfer Agent

Paul Knochel
Marthe Ketels
Martinez-Solorio D, Melillo B, Sanchez L, Liang Y, Lam E, Houk KN, * Smith III AB. * University of Pennsylvania, Philadelphia and University of California, Los Angeles, USA
Design, Synthesis, and Validation of an Effective, Reusable Silicon-Base Transfer Agent for Room-Temperature Pd-Catalyzed Cross-Coupling Reactions of Aryl and Heteroaryl Chlorides with Readily Available Aryl Lithium Reagents.

J. Am. Chem. Soc. 2016;
138: 1836-1839
Further Information

Publication History

Publication Date:
15 March 2016 (online)



The authors present a reusable, bench-stable, silicon-based transfer agent for effective room-temperature palladium-catalyzed cross-couplings of aryl chlorides with aryl lithium reagents.



DFT calculations outline the importance of the CF3 groups of the transfer agent and support a σ-bond-metathesis mechanism during transmetalation.