Abstract Diazine-bridged bisindoles are readily obtained from N-Boc-protected 3- iodoindoles and 3-iodo-7-azaindole in a pseudo three-component reaction involving a one- pot Masuda borylation–Suzuki arylation sequence. Some of the title compounds display promising cytotoxic properties. The versatility of this methodology is illustrated by a very concise total synthesis of the marine alkaloid hyrtinadine A.