title: Alkyne hydroarylation with Au N-heterocyclic carbene catalysts.
abstract: Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh(3)). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.
authors: Dipartimento di Scienze Chimiche, Università degli Studi di Padova, via Marzolo 1, 35131 Padova, Italy.
authors: Cristina
authors: C
authors: Tubaro
authors: Marco
authors: M
authors: Baron
authors: Andrea
authors: A
authors: Biffis
authors: Marino
authors: M
authors: Basato
keywords: C–H functionalization; N-heterocyclic carbenes; alkyne; cyclisation; gold; hydroarylation
references: Angew Chem Int Ed Engl. 2008;47(20):3805-10
references: 18399561
references: Chem Rev. 2008 Aug;108(8):3266-325
references: 18651778
references: Chemistry. 2005 May 6;11(10):3155-64
references: 15779093
references: Science. 2000 Mar 17;287(5460):1992-5
references: 10720319
references: Org Lett. 2007 Jul 5;9(14):2645-8
references: 17564458
references: Angew Chem Int Ed Engl. 2004 Nov 19;43(45):6183-5
references: 15549737
references: Chemistry. 2008;14(36):11310-3
references: 19006147
references: Chem Commun (Camb). 2007 Sep 7;(33):3482-4
references: 17700889
references: Chem Rev. 2007 Jul;107(7):3180-211
references: 17580975
references: Chem Commun (Camb). 2011 Jan 7;47(1):218-20
references: 20411208
references: Chem Rev. 2011 Mar 9;111(3):1657-712
references: 21391565
references: Chem Soc Rev. 2011 Mar;40(3):1358-67
references: 21103507
references: Org Biomol Chem. 2012 Dec 28;10(48):9700-8
references: 23147573
references: J Am Chem Soc. 2010 May 26;132(20):6910-1
references: 20441195
references: Chem Soc Rev. 2011 Apr;40(4):1910-25
references: 21103517
references: J Org Chem. 2009 Nov 20;74(22):8901-3
references: 19848386
references: J Am Chem Soc. 2009 Jan 21;131(2):448-9
references: 19140786
references: Chem Rev. 2008 Aug;108(8):3239-65
references: 18613729
references: J Am Chem Soc. 2009 Jun 24;131(24):8690-6
references: 19456108
references: Chem Soc Rev. 2012 Mar 21;41(6):2448-62
references: 22182942
references: Acc Chem Res. 2001 Aug;34(8):633-9
references: 11513570
references: ChemSusChem. 2010 Jul 19;3(7):834-9
references: 20623724
references: Inorg Chem. 2012 Feb 6;51(3):1778-84
references: 22268766
references: J Org Chem. 2009 Nov 20;74(22):8834-7
references: 19848384
references: Org Lett. 2012 Apr 20;14(8):2058-61
references: 22480263
references: J Am Chem Soc. 2006 Nov 15;128(45):14480-1
references: 17090030
references: J Org Chem. 2000 Nov 3;65(22):7516-22
references: 11076610
references: Org Lett. 2007 May 24;9(11):2219-22
references: 17474753
references: J Org Chem. 2004 May 28;69(11):3669-71
references: 15152995
references: J Org Chem. 2012 Sep 21;77(18):7804-14
references: 22768913