芳炔与烯基酰胺的反应：邻醌二亚甲基中间体的亲核加成。
Reaction of arynes with vinylogous amides: nucleophilic addition to the ortho-quinodimethide intermediate.
机构信息
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, China.
出版信息
Org Lett. 2013 Sep 6;15(17):4366-9. doi: 10.1021/ol4018968. Epub 2013 Aug 19.
PMID:23957502
Abstract
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.
摘要
在环境温度下，无游离 N-H 键的烯基酰胺与芳炔反应以[2+2]环加成方式进行。烯基酰胺的电子性质允许环加成产物经历容易的开环过程，导致电子偏向邻-醌二甲烷中间体。随后与醇的亲核加成得到 2-取代苯甲醛或酮。
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