Well yes, I think something would be possible. As a stab:
Sub StabAtIt()
Dim oDocS As Document, oDocT As Document
Dim lngIndex As Long
Dim oRng As Range
Set oDocS = Documents(1) 'The doc with the text to copy
Set oDocT = Documents(2) 'The doc with the CCs
Set oRng = oDocS.Range
With oRng.Find
.Style = "Heading 1"
While .Execute
lngIndex = lngIndex + 1
oRng.Move wdParagraph, 1
oDocT.SelectContentControlsByTitle("F1." & lngIndex).Item(1).Range.Text = oRng.Paragraphs(1).Range.Text
Wend
End With
lbl_Exit:
Exit Sub
End Sub