Copper-Catalyzed C-H Bond and N-H Bond Insertion Reaction Based on Azide-Ynamide Cyclization

A copper-catalyzed azide-ynamide cyclization to synthesize isoquinoline derivatives is reported. First, alpha-imino copper carbene intermediate is generated via Cu(I)-catalyzed azide-ynamide cyclization, then this copper carbene can be captured by indoles and anilines to form C-H and N-H insertion products. The notable advantages of this method include a simple procedure, mild reaction conditions and widespread availability of the substrates. Thus, this protocol provides a highly convenient and efficient route for the preparation of natural products and active molecules which contain the isoquinoline-indole or isoquinoline-aniline skeletons.