3 years ago

Micelle-Enabled Palladium Catalysis for Convenient sp2-sp3 Coupling of Nitroalkanes with Aryl Bromides in Water Under Mild Conditions

Micelle-Enabled Palladium Catalysis for Convenient sp2-sp3 Coupling of Nitroalkanes with Aryl Bromides in Water Under Mild Conditions
Faisal Ibrahim, Fabrice Gallou, Justin D. Smith, Sachin Handa, Jeremy Brals
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.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02663

DOI: 10.1021/acscatal.7b02663

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