[TwistedConf]

I need to oxidize a secondary alcohol to ketone in the presence of an unprotected secondary aromatic (aniline-type:  benzene-NH-R).  These are not common in the literature.

Dess-Martin or methods that use acidic conditions so that the amine is "protected" by protonation come to mind.

Anyone have any suggestions before I start the trials?

[discodermolide]

I appreciate the protonation route as a means of amine protection, but do you trust the amine to remain protonated throughout the entire oxidation reaction and work-up?
I don't, but then I have no idea what you will be using for the oxidation.

Better to put a Boc on that nitrogen, oxidise and remove the Boc with acid to give the amine salt.

[C-hemCards]

Discodermolide makes a valid point. That being said, I'd give it a go with Dess-Martin. I think that will probably work unless the secondary alcohol is horrendously hindered.

Another option is to add an equivalent of AcOH to the rxn mixture before the oxidation.

[Dan]

Maybe TFAA/DMSO? This should temporarily protect the aniline as the TFA amide, which should hydrolyse easily with a basic workup.