Hi Jason (and all others), there have been a lot of good suggestions offered but I think that we have all gotten a little side tracked with clever designs instead of looking at the real problem.
The original question was how to make a "D" shaped hole. and later Thomas said :-
" Yes, this is to go on an existing electric motor with this shape already on the end of it's shaft – it is also too short to cut a keyway or any other hole in it as the motor would foul onto the chuck.
I could do a simple grub screw job but the mechanism it is powering will be under a lot of resistive torque (is that a term??). In other words the motor shaft needs to have a really good grip on the arbor that requires this odd hole, otherwise it may fail and I am unsure if a grub screw is up to the job. "
This sounds like a standard motor and pulley arrangement (Thomas please confirm) which normally uses a grub screw to lock the pulley to the shaft.
My lathe has a similar arrangement with a 1kw motor with a 16mm shaft and a flat on the shaft. An aluminium vee belt pulley is only secured by an M8 grub screw. The torque from small (1440 rpm) motors is not that great and a grub screw is all that is needed. The secondary shaft and pulleys run at a much slower speed and much higher torque, therefore it is fitted with a key plus a screw to clamp it in position.
Paul.