The use of transition metal carbenes in organic synthesis represents an efficient method for the construction of new bonds. Typically accessed through the decomposition of diazo species with rhodium or copper catalyst, new methods for accessing these carbene from groups beyond diazo motifs could be potentially advantageous. Described herein are our efforts in the generation of α.β-unsaturated carbenes from the reaction of alkynes and a π-acidic transition metal, and their utility in cycloaddition reactions synthesizing various indole heterocycles. Both allyl silanes and dienes were compatible cycloaddition partners with in-situ generated carbenes for the construction of the corresponding tricyclic motifs. We also studied the regioselectivity of O-H and N-H additions into alkynes, in either an exo-dig or endo-dig type fashion, forming various enol ethers and enamines