Personnel-wise, I think these make sense. Filler would be included for salary but I'm just talking major pieces.
I've read and heard on podcasts that Riley doesn't wanna pay Whiteside. So here are some trade ideas involving him:
To Orlando for Vucevic and another young player that isn't Oladipo
To Atlanta for Al Horford
To Milwaukee for Greg Monroe
Raptors need a power forward. They've got the Knicks draft pick, which is #10 right now, the Clippers pick next year and their own picks to work with. They can package some of those with prospects for Markieff Morris, Thaddeus Young, and if they are willing to give up a rotation player as well, maybe Horford.
With news coming out of Sacramento that Karl is gonna stay, maybe Demarcus is about to go.
To Boston for the Nets lotto pick this year plus whatever players/extra picks it takes.
To Toronto for Valanciunas, the NY pick, and more picks/prospects
To Memphis for the injured Marc Gasol