Apple - How can I combine PDF files and automatically create a table of contents?

PDFCombo, new free app for Mac OS X, combines PDFs and preserves the table of contents. It can also add a TOC entry based on filename to link to first page of every contributing PDF in the combined PDF.

Download here: http://www.onekerato.com/downloads.html

PDF Pen Pro 6 is my weapon of choice for this sort of advanced processing task.

• https://itunes.apple.com/us/app/pdfpenpro-6/id609313570?mt=12

I find in PDF handling software on the Mac, you generally get what you pay for. This is premium software for advanced tasks and scripting. Their lighter version might suit your two needs as well, so check before buying.

Sejda PDF is an online and desktop cross platform toolset for editing PDF files.

The Merge PDF tool has an option to create a table of contents based on:

• Names of files being merged
• Titles of documents being merged

It has another 2 features that works nicely combined with generating the TOC:

• Generating top level bookmarks for each merged file (can wrap existing bookmarks)
• Adding the filename/document name to the footer of each merged page (to identify the source document)

Sejda PDF is free to use within limits (3 tasks per day).