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Reduction of Aryl Thiocyanates with SmI2 and Pd-Catalyzed Coupling with Aryl Halides as a Route to Mixed Aryl Sulfides

1996/01/01 by I. W. J. STILL, F. Dean Toste · 1 citation
Chemistry · #Catalytic C–H Functionalization Methods #Chemical Synthesis and Reactions #Sulfur-Based Synthesis Techniques

paper · doi:10.1021/jo961029h

openalex publication_date 1996/01/01 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/05

Abstract

A series of aryl iodides, with a range of substituents, has been successfully coupled using 10 mol % Pd catalyst with samarium thiolates, derived from the corresponding aryl thiocyanates upon reductive cleavage with SmI(2). Reactions proceed in THF at 65 degrees C in yields ranging from good to excellent and are compatible with both electron-donating and electron-withdrawing substituents, except NO(2). The reactions may also be conducted with aryl bromides although with somewhat lower yields.

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