A groundbreaking study in ligand structure-reactivity and selectivity relationships has been conducted, leading to the development of a highly regioselective heteroannulation reaction of o-bromoanilines and branched 1,3-dienes. Researchers have successfully synthesized 3-substituted indolines with exceptional selectivity and reactivity across a diverse range of functionalized substrates.
The investigation involved the utilization of N-tosyl o-bromoaniline and myrcene as model substrates to study the impact of various phosphine ligands on selectivity and reactivity in the heteroannulation reaction. Through meticulous optimization of reaction conditions and a two-round ligand screening, the team identified key ligand parameters that significantly influence selectivity in the reaction.
Utilizing a data-driven approach and linear regression analysis with phosphorus ligand parameters from the Kraken database, the researchers gained valuable insights into the factors governing selectivity in the transformation. Furthermore, density functional theory calculations supported their experimental observations and provided a deeper understanding of the selectivity-determining steps in the catalytic cycle.
The study not only sheds light on the crucial role of weak noncovalent interactions between the ligand surface and substrates in influencing reaction outcomes but also paves the way for future advancements in ligand control over carbopalladation in palladium catalysis. The researchers anticipate that their findings and predictive models for reaction selectivity will have a transformative impact on the field of olefin carbofunctionalization.
