Hidan, Zetsu, and Konan are casually disposed of.
Kakuzu is a bit tougher, but a well-placed Amaterasu should finish it, which is a problem. Itachi lacks stamina, so using his big techs are going to be draining.
Itachi has shown he can easily defeat Deidara.
Sasori will be much tougher, he can tell Itachi's best Genjutsu to eat shit, and he has enough methods to misdirect attacks and dodge them that Amaterasu is unlikely to land a solid hit, though any puppet that takes that blow is toast. Which means Itachi will have to use Susano'o, which indeed would put down Sasori.
Last and most challenging is of course Kisame. It is here that I think Itachi probably falls. Already having used Susano'o on Sasori, Itachi's chakra is going to be less than half full, maybe dangerously low. Which is very bad when fighting someone who has "drains chakra" in his powerset, and who can outmaneuver him using his impressive battlefield control abilities (Moving testicle of the leviathan), and it must be said that Kisame starts with considerably more chakra at base than Itachi does healthy, his chakra being explicitly comparable to a Biju. Fighting all of them at once? Itachi has no real chance.
One on one, Itachi would handle any of these guys, sure, but see, while being a more powerful combatant than any of them, and being generally impressive in almost all ways, Itachi actually has relatively low chakra for an S rank ninja. He simply doesn't have the stamina to take them all on in a row no rest, or take them on all at once.