Selectivity, Compatibility, Downstream Functionalization, and Silver Effect in the Gold and Palladium Dual-Catalytic Synthesis of Lactones

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• 作者：Mohammad Al-Amin ; Joel S. Johnson ; Suzanne A. Blum
• 刊名：Organometallics
• 出版年：2014
• 出版时间：October 13, 2014
• 年：2014
• 卷：33
• 期：19
• 页码：5448-5456
• 全文大小：513K
• ISSN：1520-6041

文摘

The chemo- and regioselectivity and functional group compatibility in gold and palladium cooperatively catalyzed cross-coupling reactions were determined in the synthesis of lactones; the selectivity in the gold and palladium dual-metal catalysis system was distinct from that available for the same class of substrates in systems with only gold catalysis or only palladium catalysis rather than dual catalysis. The dual-catalytic rearrangement reaction selectively promoted oxidative addition at the C鈥揙 bond over the C鈥揃r bond, providing a useful C鈥揃r bond handle for downstream functionalization showcased via Suzuki鈥揗iyaura and Sonogashira coupling reactions. Product classes were expanded from isocoumarins to three previously unpublished ring classes: pyrone, indolepyrone, and furopyrone.