Yes,

Use a Davis N-sulfonyloxaziridine (JOC 2006, 71, 8993) oxidizing reagent, many of which are commercially available. It should selectively oxidize the alkyl thioether rather than the more sterically encumbered trityl S-group to the sulfoxide. Oxidize the sulfoxide using a basic oxidant such as Oxone, or KMnO4 (JACS 98, 5715).

Nathan: Reference: Highly efficient oxidation of sulfides to sulfones with tetra-n-butylammonium hydrogen monopersulfate...., Ghaemi, A., etal, Applied Catalyst A 2009, 353, 154-159. Should , under mild conditions, not attack trityl sulfide because of steric hinderance. Difficult reaction. Other approach would be to use a different blocking group than trityl.

I used oxone to oxide Thioanisole to corresponding sulfone very recently in quantitative yield employing procedure published Organic synthesis, 1998, vol 9, p 446. You may try it out.

Hi

I can't find a precedent, but you might try a trityl with electron withdrawing groups ortho and/or para to diminish the electron availability on the Sulfur. Also, possibly use a more hindered trityl, perhaps trimesityl. Or both.

Bill

I found selective oxidation to a sulfoxide made by Bradley group TL 2004,45,1399. Could be useful? good luck!

Thank you all for your answers and for the references. I will have a closer look and investigate further. I'll let you know how it works out after the holidays. I'd rather not have to change to a different protecting group at this point. Cheers!

Friend did a lot of sulfide oxidation to sulfoxides and less hindered thiol reacts more quickly and this can be done with SeO2 in H2O2 or MCPBA simple reangentes of course do tests before the sulfone is formed after 30 minutes

Solid phase prepn., using H2O2 a soxidizing agent and hexafluoroisopropanol (HFIP) as solvent..and later trityl can be cleaved...

Thanks to Franklin Davis and Kazimierz Minksztym, we are persusing the use of H2O2 / Sc(OTf)3 developed by the Bradley group, following Org Lett., 2003, 5, 235. After obtaining the sulfoxide we will attempt to selectively oxidize to the sulfone. I'll let you know if the approach is successful.