Your description reminds me a bit of kids who have to pee as soon as they're packed into the car - no matter how many times you ask if they need the washroom before you depart.
Have you tried pre-empting the barking phase by putting him in the crate for a few minutes to get him in the right frame of mind, then letting him out to pee before he asks loudly?
Have you tried pre-empting the barking phase by putting him in the crate for a few minutes to get him in the right frame of mind, then letting him out to pee before he asks loudly?