Copper Catalyzed Huisgen 3 2 Cycloaddition of Gold I Alkynyls with Benzyl Azide Syntheses Structures and Optical Properties      
Yazarlar (6)
David V. Partyka
L.L.C., Avustralya
Lei Gao
Case Western Reserve University, Amerika Birleşik Devletleri
Thomas S. Teets
Massachusetts Institute Of Technology, Amerika Birleşik Devletleri
James B. Updegraff
Case Western Reserve University, Amerika Birleşik Devletleri
Prof. Dr. Nihal DELİGÖNÜL Case Western Reserve University, Amerika Birleşik Devletleri
Thomas G. Gray
Case Western Reserve University, Amerika Birleşik Devletleri
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale
Dergi Adı Organometallics
Dergi ISSN 0276-7333 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q4
Makale Dili İngilizce
Basım Tarihi 11-2009
Cilt No 28
Sayı 21
Sayfalar 6171 / 6182
DOI Numarası 10.1021/om9005774
Makale Linki http://pubs.acs.org/doi/abs/10.1021/om9005774
Özet
The copper(I)-catalyzed Huisgen [3 + 2] cycloaddition is a general reaction encompassing wide ranges of organoazide and primarily terminal alkyne reacting partners. Strained internal alkynes can also undergo cycloaddition with azides. We report here that tetrakis(acetonitrile)copper(I) hexafluorophosphate catalyzes the [3 + 2] cycloaddition of (phosphine)- and (N-heterocyclic carbene)gold(I) alkynyls with benzyl azide. Isolated yields of up to 96% result. The reaction protocol broadly tolerates functionalities on the alkynyl reagent. Gold(I) triazolate products form with complete 1,4-regioselectivity. Some 15 new gold(I) triazolates are reported along with crystal structures of nine. Triazolate complexes bearing polycyclic aromatic substituents show dual singlet- and triplet-state luminescence from excited states localized on the aromatic fragment. Time-resolved emission experiments find long lifetimes consistent with triplet emission parentage. Absorption and emission transitions are analyzed with time-dependent density-functional theory calculations. © 2009 American Chemical Society.
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