title: Continuous-flow synthesis of functionalized phenols by aerobic oxidation of Grignard reagents.
abstract: Phenols are important compounds in chemical industry. An economical and green approach to phenol preparation by the direct oxidation of aryl Grignard reagents using compressed air in continuous gas-liquid segmented flow systems is described. The process tolerates a broad range of functional groups, including oxidation-sensitive functionalities such as alkenes, amines, and thioethers. By integrating a benzyne-mediated in-line generation of arylmagnesium intermediates with the aerobic oxidation, a facile three-step, one-flow process, capable of preparing 2-functionalized phenols in a modular fashion, is established.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA).
authors.forename: Zhi
authors.initials: Z
authors.lastname: He
authors.forename: Timothy F
authors.initials: TF
authors.lastname: Jamison
mesh_terms: D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D010636:Phenols
keywords: Grignard reagent; chemoselectivity; flow chemistry; oxidation; phenol