Created to be an organization that would bring peace to the world, Akatsuki had its ideology destroyed and corrupted by the plans of Obito Uchiha, who co-opted its members to leverage its plan of the Eye of the Moon. This new Akatsuki was intended to capture the Jinchuuriki and extract the Tailed beasts. And because of that, they all obviously ran into the most powerful Jinchuuriki, Naruto Uzumaki. Or better, almost all.
This second version of Akatsuki had few members and, because of that, it is relatively easy to verify when they had contact with the protagonist of the series.
Deidara met Naruto when Team Kakashi and Team Guy went to rescue Gaara. At that moment, Naruto also “met” Sasori, passing.
Itachi Uchiha and Naruto have met several times.
Defeated by Naruto and the first to know the power of Rasenshuriken, Kakuzu certainly met Naruto.
Kisame met Naruto when he and Itachi went to Konoha to try to kidnap him and were stopped by Jiraiya.
Konan and Nagato they met and interacted with Naruto during the Invasion of Pain, where Naruto convinced them that he would find a way to save the world from the cycle of hatred.
Orochimaru and Naruto met many times and today they are even “allies”.
Naruto faces Tobi / Obito several times and, during one of these meetings, Black Zetsu appears too.
So the only member left was, Hidan… who, in fact, never even saw Naruto.
During the fight against Kakuzu, Hidan was captured by Shikamaru’s Shadow Jutsu and taken to the forest before Naruto arrived.
And as the result of the fight was a Hidan quartered and buried, it is possible to say that they not only never saw each other, but they will never see each other.
Naruto Shippuden, shown between the years 2007 and 2017, tells the second phase of the anime. In it, Naruto returns after two years of training with the mission to fight Akatsuki and then rescue Sasuke from the clutches of Orochimaru.
Altogether, the anime has 500 episodes (including the Naruto Shippuden fillers), and ends the story of Naruto, Sasuke, Sakura and Kakashi. In addition, the anime sets the stage for the direct continuation of the story.
You can follow Naruto in full on Crunchyroll. In addition to it, the service features classic Naruto and Boruto: Naruto Next Generations, its direct continuation.
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