Good afternoon, in these posts RandyEllsworth gave good answers, as you can do it using the ps_upload and import_file utilities
@Lyka - What version of TC? Are the items already existing in TC that the datasets will be attached to? You will be adding just PDF's, correct?
How many PDF's? Because they are not existing, look at TCXML and CSV2TCXML for creating Items and importing Datasets. You can search the forums for CSV2TCXML and find some good posts as well.
NX 11 | SW 2016 | Creo 4 | TcUA 11.4
Evaluating: AW 3.4