A phosphine-catalyzed [4+3] annulation between dinucleophilic indole derivatives and Morita−Baylis−Hillman (MBH) carbonates was discovered by using the N1 and N4′ or C4′ nucleophilicities of indole precursors, which provides an efficient and facile access to in-dole-1,2-fused 1,4-diazepinones and azepines in good to high yields in one step, in which indoles act as four atom synthons. Various transformations of products illustrate promising applications of the given protocols.