Abstract
A new and efficient Pd(II)/AgNO3-cocatalyzed homocoupling of aromatic terminal alkynes is described. Various symmetrical 1,4-disubstituted-1,3-diynes are obtained in good to excellent yields. This protocol employs a loading with relatively low palladium(II) in aqueous media under aerobic conditions.
Highlights
Compounds which contain a 1,4-disubstituted-1,3-diyne linkage have been found in applications in areas ranging from pharmaceuticals with anti-inflammatory, antibacterial, antitumor, and antifungal activities to a large variety of polymers, biologically active molecules, and supramolecular materials with appreciable photoelectrical properties [1,2,3,4,5,6]
The homocoupling reaction of terminal alkyne is the classical protocol, and the choice of the catalytic system is a pivotal factor for the synthesis of symmetrical 1,3-diynes [7,8,9,10]
Apart from copper salts, catalysts, based on other transition metals such as Ni [19], Co [20], Au [21], and Ti [22] have been employed in terminal alkyne homocoupling reactions
Summary
Compounds which contain a 1,4-disubstituted-1,3-diyne linkage have been found in applications in areas ranging from pharmaceuticals with anti-inflammatory, antibacterial, antitumor, and antifungal activities to a large variety of polymers, biologically active molecules, and supramolecular materials with appreciable photoelectrical properties [1,2,3,4,5,6]. The homocoupling reaction of terminal alkyne is the classical protocol, and the choice of the catalytic system is a pivotal factor for the synthesis of symmetrical 1,3-diynes [7,8,9,10]. Palladium complexes in combination with Cu salts are traditionally employed as cocatalysts for the reaction [11,12,13,14,15,16,17,18]. Apart from copper salts, catalysts, based on other transition metals such as Ni [19], Co [20], Au [21], and Ti [22] have been employed in terminal alkyne homocoupling reactions. The metal-free cocatalyst palladium-catalyzed homocoupling reactions have been described [24,25].
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