title: Gold-catalyzed cyclizations of cis-enediynes: insights into the nature of gold-aryne interactions.
abstract: Golden aryne? Gold aryne complexes are inferred as transition states in dual gold-catalyzed cyclizations of cis-enediynes (see scheme; DCE = 1,2-dichloroethane). They are better described as ortho-aurophenyl cations, which react with weak nucleophiles and undergo facile intramolecular insertions into C(sp(3))-H bonds. Indanes, fused heteroarenes, and phenol derivatives are readily prepared using this method.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA.
authors.forename: Youliang
authors.initials: Y
authors.lastname: Wang
authors.forename: Akop
authors.initials: A
authors.lastname: Yepremyan
authors.forename: Subir
authors.initials: S
authors.lastname: Ghorai
authors.forename: Robert
authors.initials: R
authors.lastname: Todd
authors.forename: Donald H
authors.initials: DH
authors.lastname: Aue
authors.forename: Liming
authors.initials: L
authors.lastname: Zhang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D053281:Enediynes / Q000737:chemistry* / Q000378:metabolism; D006046:Gold / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D053281:Enediynes; D006571:Heterocyclic Compounds; D010636:Phenols; D006046:Gold
keywords: CH insertion; arynes; gold; heterocycles; homogeneous catalysis