Synthesis of nitrogen heterocycles via Pd-catalyzed cross-coupling of o-alkenyl anilides with vinylic halides and triflates
1998; Elsevier BV; Volume: 54; Issue: 34 Linguagem: Inglês
10.1016/s0040-4020(98)00589-4
ISSN1464-5416
AutoresRichard C. Larock, Paola Pace, Hoseok Yang, Charles E. Russell, Sandro Cacchi, Giancarlo Fabrizi,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoThe 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 π-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.
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