I think Green and Smith are too similar of players, but I do think that something like this might work for both teams.
Monroe, Jerekbo, Villanueva
for
Green, Bradley, Bass
So Detroit gets a SF for their mismatched though talented PF (who is also going to be cheaper long term), upgrade the backup PF (Bass from Jerekbo), and get a young defensive guard that can provide some much needed defense to their backcourt.
Boston obviously gets Monroe who instantly is the most talented player on the roster (aside from Rondo). He is going to get a big contract this summer, but I think it would be worth it. Monroe, Sullinger, and Olynyk going forward is a good start down. Add them to the high draft pick this summer and Rondo and you have the beginnings of a nice little team.