220405-65-2Relevant academic research and scientific papers
Tridentate SCS palladium(II) complexes: New, highly stable, recyclable catalysts for the Heck reaction
Bergbreiter, David E.,Osburn, Philip L.,Liu, Yun-Shan
, p. 9531 - 9538 (2007/10/03)
A new pincer-type SCS ligand containing Pd(II) is a simple, robust catalyst for Heck chemistry using a variety of alkene acceptors and aryl iodides. It is less active with aryl bromides. While certain palladium-(II) species insert slowly into the aryl C-H bond of an unsubstituted version of this ligand, the introduction of activating groups into the 5 position of the aromatic ring readily allows quantitative metal insertion. These ligands were synthesized and attached to soluble polymers by simple modification of inexpensive starting materials. For example, both 5-oxy and 5-amido SCS ligands were successfully appended to 5000 Mn poly-(ethylene glycol) via ether or amide linkages, respectively. Both the 5-oxo and 5-amido complexes are active as Heck catalysts in DMF solution in air. The PEG-bound 5-amido-SCS-Pd complex was recycled via solvent precipitation three times with no observed catalyst deactivation. While the 5-amido-SCS-Pd complexes are very robust, their 5-oxo counterparts decompose slowly under certain conditions. These SCS catalysts are analogous to PCP-type catalysts previously reported in the literature but avoid the requirement of an air-sensitive phosphine synthesis.
