Sadly it's probably never going to happen.
i don't see why not. Ranieri usually played with 4 attackers, DP, Trez, Nedved,Palla/Iaquinta ... in a 442 it is just a matter of arranging it differently on the field. with nedved or camo playing centrally and Palla on the left with DP as a right forward. It will give the offense much more explosiveness and creativity.
The defense also would not be compromised given Zanetti's ability to snuff out danger and Sissoko's tireless workrate in the midfield.
I think it could easily work. It would also be an effective weapon to be able to make a drastic change to the offense without having to make a sub (if palla does start on the right midfield in a 442 .. he can switch to the left) or if Camo or Nedved are having a poor game we have another outlet.