title: Reaction of arynes with vinylogous amides: nucleophilic addition to the ortho-quinodimethide intermediate.
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.
authors: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, China.
authors: Ran
authors: R
authors: Li
authors: Xuemei
authors: X
authors: Wang
authors: Zhibin
authors: Z
authors: Wei
authors: Chunrui
authors: C
authors: Wu
authors: Feng
authors: F
authors: Shi
mesh_terms: D000577:Amides / Q000737:chemistry*; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001547:Benzaldehydes; D007659:Ketones