Reaction of Arynes with Vinylogous Amides: Nucleophilic Addition to the <i>ortho</i>-Quinodimethide Intermediate
作者:Ran Li、Xuemei Wang、Zhibin Wei、Chunrui Wu、Feng Shi
DOI:10.1021/ol4018968
日期:2013.9.6
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.