A series of ruthenium complexes can perform the acceptorless dehydrogenation of diols as well as the reaction of amines and alcohols to form ester, lactam, and amide products. The ligand criteria necessary for high catalytic activity are identified to guide future catalyst development for amide formation from amines and alcohols. These complexes can be employed in a dehydrogenative Paal–Knorr pyrrole synthesis to give 2, 5-dimethyl-N- ...