Substituted azafluorenones were synthesized from different dihalogeno diaryl ketones under palladium catalysis by combining either Suzuki or Heck coupling with direct cyclizing arylation. Conditions were identified to allow both auto-tandem processes to proceed successfully from 3-(bromobenzoyl)- or 3-benzoyl-4-bromo-2-chloropyridines, as well as 4-benzoyl-2,3- and 4-benzoyl-2,5-dichloropyridines.