Communicator can be configured to intergrate with Outlook.

This would need to be configured from within the Communicator desktop

Navigate to 'Tools - Preferences' and select 'Contacts' followed by 'Outlook'.

Ensure the following setting is enabled and press OK.

Now that the integration is enabled, the following option should be enabled in Outlook:

Should this button not appear, the plugin is likely disabled/inactive within Outlook.

To check Navigate to 'File - Options' and select 'Add-ins'.

Look for the Communicator Outlook Plugin:

If it is listed in 'Inactive' or 'Disabled' you can reenable it by selecting 'Go'.

Ensure the Communicator Outlook Plugin is checked:

Press OK and restart Outlook and the option should appear.