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This is possible using Tmux and iTerm2. I am using Tmux version 3.0, iTerm2 version 3.3 and macOS Catalina. It probably works for a few earlier version but I have not researched it.
First, you need to enable iTerm2 to access the system clipboard. It is not enabled by default.
iTerm2 -> Preferences -> Selection -> [check] Applications in terminal may ...
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