The palladium-catalyzed cross-coupling of o-allylic and o-vinylic anilides with vinylic halides and triflates produces substituted nitrogen heterocycles in good to high yields by a process involving vinylpalladium addition to the olefin, rearrangement to a pi-allylpalladium intermediate and subsequent intramolecular nucleophilic displacement of palladium. Different reactivity and regioselectivity in the palladium migration have been observed with different substituted alkenyl anilides. (C) 1998 Elsevier Science Ltd. All rights reserved.
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Univ Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, BrazilUniv Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, Brazil
Nichele, Tatiana Z.
Favero, Cristiano
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Univ Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, BrazilUniv Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, Brazil
Favero, Cristiano
Monteiro, Adriano L.
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Univ Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, BrazilUniv Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, Brazil