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A switchable access to ethenylphosphorylamides and chloroethenylphosphorylamides from phosphorylamides and alkenes has been disclosed herein. With the assistance of Pd(OAc)2, a catalytic loading of CuCl2 or CuBr (20 mol‐%) led to the occurrence of dehydrogenative cross coupling reactions with high efficiency and broad substrate scope, while 1.0 equivalent of CuCl2 rendered the dehydrogenative amidochlorination reactions to take place with high stereoselectivity. [ABSTRACT FROM AUTHOR]