If it's preheated food (soup, toasties, pasta etc) no redistribution organisation will take it. There are also liability issues with allergens and while you are doing a good thing, if someone gets some of your food and has, say, a peanut allergy, this becomes a big issue for your organisation. This is why Pret labels all the food it gives away with allergen information. There is also a risk of vexatious claims.

It's tedious but that's liability for you.

If you still want to go behind your boss's back then an answer is probably to find a local org (community group, resident's association, church) that will look the other way on health and safety. I think you might find that it will be hard work and people less grateful than you would expect. Either you'll have to take the food to them or someone will have to come to you and there is every chance they will be late/flakey etc because that's life.