Ullman type coupling, with

The copper-catalysed, Ullman-type coupling of aryl, heteroaryl and alkenyl halides may be achieved at ambient temperature using copper(I) thiophene-2-carboxylate as catalyst.60 A new semiconducting poly(anthraquinone-l,5-diyl) with nitro groups at the 4- and 8-positions has been prepared by Ullman-type coupling using metallic copper or a zerovalent nickel complex as catalyst.61... 

The Ullman-type coupling of 3-pyridylcopper with aryl iodides has been reported yields are improved when the arylcopper is stabilized by the addition of an equivalent of triphenylphosphine (equation 53)75. 

In Ullman-type coupling, aryl boronic acids are much more efficient coupling partners with amines and phenols as compared with aryl halides. They successfully couple at room temperature in the presence of a copper acetate/triethylamine (or pyridine) catalyst system and the corresponding arylated products were provided in high yields (Scheme 15.20). Similarly, aryl boronic acids are successfully coupled with structurally and electronically diverse substrates such as amides and sulfonamides to afford the corresponding IV-arylated products. 

We next turned our attention to utilization of 2-fluoro-4-iodoaniline (15), hoping to displace the iodide with methoxide under Ullman-type conditions.(77) Literature precedent for effecting this type of coupling on the free aniline... 

Organocopper intermediates are involved in another broad class of reactions which accomplish the coupling of two organic substrates. The classical example of this type of reaction is the Ullman coupling of aryl halides, which is usually done with a copper-bronze alloy. Good yields in this reaction are limited to halides with electron-attracting substituents. Mechanistic and synthetic work has revealed the... 

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