Additive which promotes the Heck coupling reaction of unactivated aryl chlorides with alkenes, catalyzed by Pd(II) in the presence of Tetraphenyl-phosphonium chloride: Angew. Chem. Int. Ed., 37, 481 (1998). The combination with Bis(benzonitrile)dichloropalladum constitutes a highly active phosphine-free catalyst system for Heck reactions of aryl bromides: Tetrahedron Lett., 39, 8449 (1998); see also: Tetrahedron Lett., 39, 8449 (1998). Promotes the copper(I)-catalyzed Ullmann-type coupling of aryl bromides and iodides with amines: Org. Lett., 5, 2453 (2003), and phenols: Org. Lett., 5, 3799 (2003), to give substituted anilines and diaryl ethers, respectively. Aryl iodides can also be coupled with aliphatic alcohols to give aryl alkyl ethers: Synlett, 243 (2007). In combinatiion with CuI, vinyl halides with phenols give aryl vinyl ethers: Synlett, 1767 (2005).
