In recent years, combining transition metal catalysis and organocatalysis has emerged as a promising strategy for developing new and valuable reactions, attracting considerable attention due to its potential for unprecedented transformations not achievable by either approach alone.1 This integration has yielded three types of catalytic activities: cooperative, synergistic, and sequential.2 Though still in its early stages, three main categories have been identified: (i) transition metal associated with a ligand scaffold incorporated on a chiral cation; (ii) pairing of chiral cation with transition metal 'ate' complexes; and (iii) coupling of chiral cation with a transition metal associated with an achiral anion containing a ligand scaffold. These strategies have successfully been applied to various organic transformations, including alkylation, cycloaddition, dihydroxylation, oxohydroxylation, sulfoxidation, epoxidation, and C–H borylation.3 This development represents an effective approach to enhancing cooperation between chiral cations and transition metals, thereby augmenting the versatility and capability of both catalyst forms. In this research proposal seminar, we aim to explore the synthesis of a novel non-chiral sulfonate anion phosphine ligand paired with chiral cations such as bisguanidinium and pentanidiums.4 Additionally, this catalyst will be employed in various enantioselective organic transformations, including C-C and C-heteroatom bond formation, with an emphasis on evaluating selectivity and reactivity.
Scheme 1. Ion-paired chiral catalyst for asymmetric palladium catalysis

References:
1. Shao, G.; Zhang, H. Chem. Soc. Rev., 2009, 38, 2745–2755.
2. Shao, G.; Zhenting, D. Chem. Soc. Rev., 2013, 42, 1337-1378.
3. Choon Hong, T,; Xinyi, Y. Chem. Sci., 2021, 12, 533-539.
4. Choon Hong T,; Xinyi, Y,; Kek, F. ACS Catal. 2020, 10, 4, 2684–2691.