title: Arynes double bond insertion/nucleophilic addition with vinylogous amides and carbodiimides.
abstract: Arynes are shown to insert into some C═X double bonds, leading to benzannulated four-membered rings. The strain of these rings allow for a ready, spontaneous opening to afford o-quinomethide analogues. Subsequent nucleophilic addition re-aromatizes the intermediates to achieve ortho-difunctionalization of arynes. In this report, we describe the aryne insertion into the C═C double bonds of vinylogous amides and the C═N double bonds of carbodiimides. The correlation and comparison with aryne single bond insertion chemistry will be discussed. Computational studies for the ring-opening step, as well as the nature of the o-quinomethide intermediates, will also be discussed.
authors.forename: Ran
authors.initials: R
authors.lastname: Li
authors.forename: Huarong
authors.initials: H
authors.lastname: Tang
authors.forename: Haixing
authors.initials: H
authors.lastname: Fu
authors.forename: Hailong
authors.initials: H
authors.lastname: Ren
authors.forename: Xuemei
authors.initials: X
authors.lastname: Wang
authors.forename: Chunrui
authors.initials: C
authors.lastname: Wu
authors.forename: Chao
authors.initials: C
authors.lastname: Wu
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000577:Amides; D002234:Carbodiimides