Reaction of Arynes with Vinylogous Amides: Nucleophilic Addition to the ortho-Quinodimethide Intermediate

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• 作者：Ran Li ; Xuemei Wang ; Zhibin Wei ; Chunrui Wu ; Feng Shi
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：15
• 期：17
• 页码：4366-4369
• 全文大小：266K
• 年卷期：v.15,no.17(September 6, 2013)
• ISSN：1523-7052

文摘

The reaction of arynes with vinylogous amides containing no free N鈥揌 bonds proceeds in a [2 + 2] cycloaddition fashion at ambient temperature. The electronic properties of the vinylogous amides allow for the cycloadducts undergoing a facile ring-opening process, leading to electronically biased ortho-quinodimethide intermediates. Subsequent nucleophilic addition with alcohols affords 2-substituted benzaldehydes or ketones.