Because all of his hundreds of clones were busy trying to find sasuke.
I told you how current naruto can break out of itachi's non-mangekyou genjutsu. Yes that naruto was still weaker than itachi.
Why would you think making many clones can make the user weaker? each clone has it's own mind and thinking, although Naruto controls their movements being the main one.. for example, Naruto created many Sage Mode clones in this war, it did take his Chakra out but it didn't make him weaker by any means..
Also, when he fought Itachi for the 3rd time, he could've used like 10 more clones or so to beat him like he did to Kakuzu, right? he knew that his clones wont work on him, that's why he didn't bother making any and charged on him instead..
Magnitude 13 facepalm
I even said in that very post that naruto will not get out of itachi's tsukuyomi, but will be able to get out of itachi's basic genjutsu.
All we've seen so far Naruto being unable to get out of his basic Genjutsu's, so I don't think being in Sage Mode will change that fact..
For now on I want you to spend a lot of time thinking before you make a statement like this.
If its true that you have to be as good as itachi at genjutsu in order to break out of his regular genjutsu, then if itachi were to fight anyone in the narutoverse, save madara, he would fodderize them in an instant because he is better than them. You have to think about applying statements that you make to other circumstances in order to test them to see if they will be true or not.
And I stand of what I say, he was able to beat most of his opponents with just his basic Genjutsu's, and they were all strong as hell.. someone like Orochimaru or Deidara aren't regular Shinobi's at all..
Wow kurenai gets out of his genjutsu and that was just through pain. post timeskip Naruto partially gets out of itachi's genjutsu. It is stated that excellent chakra control allows you to break out of genjutsu. Naruto has magnificent chakra control. Itachi's basic genjutsu will be broken out of.
So you are pretty much saying that if itachi fights someone like nagato, who is not as good as him in genjutsu, then nagato will instantly get beaten by basic genjutsu?
He didn't want to kill anyone back then, he may have simply stopped it so she would dodge his next attack.. he also stopped his Tsukuyomi so Kakashi can see the daylight again..
No, I'm not saying that Itachi can beat Nagato with just his basic Genjutsu's, but he has like 80% of beating him that way.. since Nagato's weakness is Genjutsu (only..)