the reason naruto couldn't break itachis genjutsu wass because it was so high level and caused him such intense pain that even his chakra couldn't break it.
naruto has a much more powerful chakra, kakshi has no chance of breaking it.
you should reread the manga and see how break a genjutsu...
it's not naruto's powerfull chakra that will break genjutsu unless kyubi helps him...
sakura and chiyo don't have a powerfull chakra and they broke it easily as kakashi.
furthermore itachi has almost nothing in ninjutsu whereas
kakashi got suiton,doton,raiton
itachi got only katon and suiton.
doton>suiton
suiton>katon
raiton>suiton (see darui vs suigetsu)
itachi has no chance to win.