In general Buchwald-Hartwig couplings work with an amine and aromatic halides.But there are examples with vinyl bromide by using slightly modified method.(Refer the following paper:-M. C. Willis, J. Chauhan, W. G. Whittinham, Org. Biomol. Chem., 2005, 3, 3094-3095).
Yes your correct!It is possible to generate enamine!But i have to work on the remaining part of your question!!!!
Give me some time!!!!