29865-67-6Relevant academic research and scientific papers
Micelle-enabled palladium catalysis for convenient sp2-sp3 coupling of nitroalkanes with aryl bromides in water under mild conditions
Brals, Jeremy,Smith, Justin D.,Ibrahim, Faisal,Gallou, Fabrice,Handa, Sachin
, p. 7245 - 7250 (2017)
The efficacy of custom surfactant FI-750-M, designed to mimic polar solvents such as DMF and 1, 4-dioxane, has been demonstrated with the palladium-catalyzed sp2-sp3 coupling of nitroalkanes to aryl bromides using a heteroleptic palladium catalyst under unprecedentedly mild conditions. Optimized reaction conditions mostly provided good yields up to gram scale, with high selectivity and functional group tolerance for a wide scope of aryl bromides. Use of surfactant FI-750-M makes water the gross reaction medium and enables in-flask recycling. The behavior of the surfactant has been elucidated with DLS and cryo-TEM measurements, and mechanistic investigations have revealed the importance of the π-allyl ligand in the catalytic cycle.
