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A New Family of Nucleophiles for Photoinduced, Copper-Catalyzed Cross-Couplings via Single-Electron Transfer: Reactions of Thiols with Aryl Halides Under Mild Conditions (0C)

Christopher Uyeda, Yichen Tan, Gregory C. Fu* and Jonas C. Peters*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California, 91125, United States, Email: gcfucaltech.edu, jpeterscaltech.edu

C. Uyeda, Y. Tan, G. C. Fu, J. C. Peters, J. Am. Chem. Soc., 2013, 135, 9548-9552.

DOI: 10.1021/ja404050f


Abstract

A versatile photoinduced, copper-catalyzed method enables the coupling of aryl thiols with aryl halides at 0C using inexpensive CuI as a precatalyst without the need for an added ligand. The reaction is effective for a wide range of coupling partners. Mechanistic investigations are consistent with photoinduced C-S cross-couplings following a SET/radical pathway for C-X bond cleavage (via a Cu(I)-thiolate).


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Key Words

diaryl sulfides


ID: J48-Y2013