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Phenyldithiocarbamates: Efficient Sulfuration Reagents in the Chan–Lam Coupling Reaction
Author(s) -
Cheng Yu,
Liu Xing,
Dong ZhiBing
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701631
Subject(s) - chemistry , dithiocarbamate , reagent , phenylboronic acid , combinatorial chemistry , substrate (aquarium) , ligand (biochemistry) , coupling reaction , organic chemistry , catalysis , biochemistry , oceanography , receptor , geology
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.