Palladium(II)-Catalyzed Cyclizative Cross-Coupling of ortho-Alkynylanilines with ortho-Alkynylbenzamides under Aerobic Conditions†
Dr. Bo Yao
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch
Search for more papers by this authorDr. Qian Wang
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch
Search for more papers by this authorCorresponding Author
Prof. Dr. Jieping Zhu
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch===Search for more papers by this authorDr. Bo Yao
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch
Search for more papers by this authorDr. Qian Wang
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch
Search for more papers by this authorCorresponding Author
Prof. Dr. Jieping Zhu
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch
Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch===Search for more papers by this authorWe thank the EPFL (Switzerland), Swiss National Science Foundation (SNSF), and Swiss National Centers of Competence in Research NCCR Chemical Biology for financial support.
Graphical Abstract
Born to couple: The Pd(OAc)2-catalyzed reaction of o-alkynylanilines (1) with o-alkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a tetrasubstituted double bond. Mechanistic studies indicate that the reaction is initiated by aminopalladation with subsequent oxypalladation, N-demethylation, and reductive elimination.
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