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Synfacts 2016; 12(4): 0397
DOI: 10.1055/s-0035-1561806
DOI: 10.1055/s-0035-1561806
Metal-Mediated Synthesis
Palladium Cross-Couplings with a Silicon-Based Transfer Agent
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
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)
Significance
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.
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Comment
DFT calculations outline the importance of the CF3 groups of the transfer agent and support a σ-bond-metathesis mechanism during transmetalation.
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