Lei Gao - Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide.  Syntheses, Structures, and Optical Properties

Document created by Lei Gao on Aug 22, 2014
Version 1Show Document
  • View in full screen mode

  Publication Details (including relevant citation   information):

  Organometallics, 2009, 28(21), 6171-6182


  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.

  Address (URL): http://pubs.acs.org/doi/abs/10.1021/om9005774?prevSearch=%255Bauthor%253A%2BThom as%2BGray%255D%2BNOT%2B%255Batype%253A%2Bad%255D%2BNOT%2B%255Batype%253A%2Bacs- t oc%255D&searchHistoryKey=