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Is it possible to actiavte a Custom Link in SF from outside SF?

More specifically - I have an Scontrol link that generates an email and sends it to specific people. I want to be able to automate this sending function from some place like Demand Tools to be set to run automatically on a schedule. Any ideas?

You can create an Apex webservice that something like Demandtools could (potentially) call to automate this type of function.  I'm not sure if you can get Demandtools to actually call an Apex webservice right now, but that's generally the path to take.
But to your original question, no, only a Salesforce user can call an Scontrol.  Scontrols can only be run in the context of a browser and triggered by a user action.  Apex webservices can be programatically triggered though.
If you've written the s-control and are happy for the batch to be run on a local windows OS machine then consider the scripting toolkit as a possible solution. You can migrate the existing s-control with very little effort. I've used it to schedule s-controls no probs. Hope this helps.