Pd/C-Catalyzed Cyclizative Cross-Coupling of Two ortho-Alkynylanilines under Aerobic Conditions: Synthesis of 2,3’-Bisindoles

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.


Published in:
Chemistry - A European Journal, 21, 20, 7413-7416
Year:
2015
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
0947-6539
Keywords:
Laboratories:




 Record created 2015-05-05, last modified 2018-03-17


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