Chiral, Air Stable, and Reliable Pd(0) Precatalysts Applicable to Asymmetric Allylic Alkylation Chemistry
David Leitch and Stellios Arseniyadis jointly developed a range of new chiral, air stable and reliable Pd(0) precatalysts.
In the realm of homogeneous catalysis for organic synthesis, there are two major methods for generating catalytically active species, according to Professor David Leitch, from the University of Victoria in Canada, who explained: “Most common for organopalladium catalysis is the in situ assembly of an active complex through combination of a metal precursor compound and the ancillary ligand, both added separately to the reaction mixture. While this is arguably convenient, it is also often inefficient and unreliable as ligand metalation rates may be slow and multiple species can be generated, while changes of the metal–ligand stoichiometry can greatly affect performance. There are two approaches to this problem: either design advanced metal precursor compounds able to rapidly and reliably generate active species or use single-component precatalysts where the appropriate ancillary ligand is already installed to give a stable complex.” Prior work from Professor Leitch’s group sought to take both approaches by designing stable Pd(0) species able to function as in situ precursors and as a platform for generating single-component catalysts. When the key compound, DMPDAB-Pd-MAH, was first reported in 2021, Dr. Stellios Arseniyadis from Queen Mary University of London (UK) reached out to us the Leitch group to inquire if this compound could be used to replace common Pd(0) catalysts, in particular Pd2(dba)3, in the context of asymmetric allylic alkylation (AAA) chemistry. This was the beginning of their collaboration to build better catalysts for this family of enantioselective reactions.
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