A palladium-catalyzed cyclizative cross-coupling of two o-alkynylanilines to 2,3’-bisindoles under aerobic oxidative conditions was developed. Mechanistic studies suggested that the two catalytic cycles, namely the formation of 3-alkynylindoles 8 and their subsequent cyclization to bisindoles 5, are temporally separated. The aminopalladation of 3-alkynylindoles 8 occurred only after all the N,N-dialkyl-o-alkynylanilines were consumed. The solid support (activated charcoal) played a crucial role in the second intramolecular aminopalladation process.
Rolf Gruetter, Cristina Ramona Cudalbu, Bernard Lanz, Mor-Miri Mishkovsky, Jocelyne Bloch, Arnaud Comment
Davide Ferri, Oliver Kröcher, Adrian Marberger, Rob Jeremiah G. Nuguid
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