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Design, Synthesis, and Validation of an Effective, Reusable Silicon-Based Transfer Agent for Room-Temperature Pd-Catalyzed Cross-Coupling Reactions of Aryl and Heteroaryl Chlorides with Readily Available Aryl Lithium Reagents

Dionicio Martinez-Solorio, Bruno Melillo, Luis Sanchez, Yong Liang, Erwin Lam, K. N. Houk* and Amos B. Smith, III*

*University of Pennsylvania, Philadelphia, Pennsylvania 19104, University of California, Los Angeles, California 90095, United States, Email: houkchem.ucla.edu, smithabsas.upenn.edu

D. Martinez-Solorio, B. Melillo, L. Sanchez, Y. Liang, E. Lam, K. N. Houk, A. B. Smith, III, J. Am. Chem. Soc., 2016, 138, 1836-1839.

DOI: 10.1021/jacs.5b13260 (free Supporting Information)


Abstract

A reusable silicon-based transfer agent enables effective room-temperature palladium-catalyzed cross-coupling reactions (CCRs) of aryl and heteroaryl chlorides with readily accessible aryl lithium reagents. The crystalline, bench-stable siloxane transfer agent is easily prepared via a one-step protocol. Importantly, this green CCR protocol generates LiCl as the only stoichiometric waste.

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Recyclable Polystyrene-Supported Siloxane-Transfer Agent for Palladium-Catalyzed Cross-Coupling Reactions

M. H. Nguyen, A. B. Smith, III, Org. Lett., 2014, 16, 2070-2073.


Key Words

Hiyama Coupling, Biaryls


ID: J48-Y2016