Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides
We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).
Sahoo, Santosh K.,Jamir, Latonglila,Guin, Srimanta,Patel, Bhisma K.
experimental part
p. 2538 - 2548
(2010/12/29)
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