Eneos Corp. (Tokyo) has announced the development of alkylphosphine with a triisobutylene (TIB) backbone (TIB phosphine ligand), a high-performance ligand for nickel-catalyzed coupling reactions, in collaboration with Prof. Kouki Matsubara, Faculty of Science, Fukuoka University. To practically apply this ligand to pharmaceuticals manufacturing and other purposes, ENEOS has signed a licensing agreement with Hokko Chemical Industry Co., Japan’s largest phosphine compound manufacturer. Hokko Chemical Industry plans to launch sales of small-quantity samples of the TIB phosphine ligand this September.
Although the Suzuki-Miyaura cross-coupling reaction, in which an organohalogen compound reacts with an organoboron compound by means of a palladium catalyst to link them together via the carbon-carbon bond, is frequently used in production of pharmaceuticals, pharmaceutical intermediates and functional materials, it faces various problems including toxicity and the high costs of palladium and ligand, as well as challenges associated with handling alkylphosphine ligands in air and limited reaction yields.
Eneos developed a high-performance ligand for nickel-catalyzed coupling reactions, and Hokko Chemical Industry will launch sales in September (Source: Eneos)
Eneos developed a solution designed to tackle these problems — the world’s first catalyst design in which a phosphine ligand consisting of a primary alkyl group with two tert-butyl groups in remote positions attached to a phosphorus atom improves the activity of nickel-catalyzed coupling reactions. This has enabled the group to successfully synthesize and isolate phosphine ligands with a TIB backbone that is derived from petrochemicals and can be procured with lower cost. This TIB phosphine ligand is stable in air and can achieve a higher yield than before, depending on combinations of reactants, using coupling reactions with nickel catalysts that can be obtained more easily than palladium (patent pending). The details of these results will be presented at both theInternational Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS) and the Symposium on Organometallic Chemistry, scheduled to be held in September this year