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:
houk
chem.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
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.
see article for more examples
M. H. Nguyen, A. B. Smith, III, Org. Lett., 2014, 16, 2070-2073.
Key Words
ID: J48-Y2016
