Pd₂(dba)₃/P(i-BuNCH₂CH₂)₃N-Catalyzed Stille Cross-Coupling of Aryl Chlorides

The Pd₂(dba)₃/P(i-BuNCH₂CH₂)₃N (1d) catalyst system is highly effective for the Stille cross-coupling of aryl chlorides with organotin compounds. This method represents only the second general method for the coupling of aryl chlorides. Other proazaphosphatranes possessing benzyl substituents also generate very active catalysts for Stille reactions. Noteworthy features of the method are:  (a) commercial availability of ligand 1d, (b) the wide array of aryl chlorides that can be coupled, and (c) applicability to aryl, vinyl, and allyl tin reagents.