Phenyldithiocarbamates: Efficient Sulfuration Reagents in the Chan–Lam Coupling Reaction

Publisher: John Wiley & Sons Inc

E-ISSN: 1099-0690|2018|6|815-820

ISSN: 1434-193x

Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol.2018, Iss.6, 2018-02, pp. : 815-820

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Abstract

The Chan–Lam coupling reaction starting from phenyldithiocarbamates and phenylboronic acids is reported. To avoid using the volatile, hazardous, and foul‐smelling thiols, which are sometimes expensive and not sufficiently available, phenyldithiocarbamates can be employed. They are demonstrated to be good sulfuration reagents in the Chan–Lam coupling to prepare biaryl sulfides. By using this protocol, dithiocarbamate substrates with a wide range of functional groups including electron‐rich and electron‐deficient ones are explored to obtain the desired substituted biaryl sulfides smoothly. This method is ligand‐free, has a broad substrate scope, enables good yields, and is easy to perform. It provides a facile and convenient preparation of biaryl sulfides.