Organic letters

Reaction of arynes with vinylogous amides: Nucleophilic addition to the ortho-quinodimethide intermediate

R Li, X Wang, Z Wei, C Wu, F Shi

文献索引：Li, Ran; Wang, Xuemei; Wei, Zhibin; Wu, Chunrui; Shi, Feng Organic Letters, 2013 , vol. 15, # 17 p. 4366 - 4369

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被引用次数: 16

摘要

The reaction of arynes with vinylogous amides containing no free N–H 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.