One-pot approach to installing eight-membered rings onto indoles.

Ring fusion: The Pd(0)-catalyzed reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and propargylic bromides affords dihydrocycloocta[b]indoles (see scheme; M.S. = molecular sieves, TFP = tris(2-furyl)phosphine, Ts = 4-toluenemethanesulfonyl), and proceeds by carbon-carbon coupling, [1,5]-hydrogen migration, and electrocyclization. The newly established method was used to efficiently access iprindole.