A practical and efficient synthesis of 11-aryldibenzooxa/thiazepines is achieved, via a late-stage and two-step C11–H arylation of simple dibenzooxa/thiazepines. The adoption of Grignard addition and DDQ dehydrogenation allows for operationally simple and chemically reliable, step-efficient, and high-yielding transformations. The two-step and one-pot procedures provide excellent yields. The gram-scale experiment demonstrates the promising synthetic potentials in large-scale applications, and the advantages of this method are also highlighted in the efficient synthesis of an H460TaxR inhibitor.
Key words
arylation - Grignard reaction - dehydrogenation - heterocycle - fused-ring systems
