Review Articles
Gold coordination during homogeneous alkyne and allene cyclisation catalysis: Coordination to substrates, to ancillary ligands and in intermediates
Submitted: 05 October 2010 | Published: 16 March 2011
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Helgard G. Raubenheimer, Stellenbosch University, South AfricaHubert Schmidbaur, Technische Universität München, Germany
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References
Schmidbaur H, Schier A. Gold η2-coordination to unsaturated and aromatic hydrocarbons: The key step in gold-catalyzed organic transformations. Organometallics. 2010;29:3–27. doi:10.1021/om900900u
Schmidbaur H, Schier A. Organogold chemistry. In: Crabtree RH, Mingos DMP, editors. Comprehensive organometallic chemistry III. Vol. 2. Oxford: Elsevier, 2006; p. 251–308.
Salvi N, Belpassi L, Tarantelli F. On the Dewar-Chatt-Duncanson model for catalytic gold(I) complexes. Chem Eur J. 2010;16:7231–7239. PMid:20468042
Gorin DJ, Toste FD. Relativistic effects in homogeneous gold catalysis. Nature. 2007;446:395–403. doi:10.1038/nature05592, PMid:17377576
Hashmi ASK. Gold catalyzed organic reactions. Chem Rev. 2007;107:3180–3211. doi:10.1021/cr000436x, PMid:17580975
Arcadi A. Alternative synthetic methods through new developments in catalysis by gold. Chem Rev. 2008;108:3266–3325. doi:10.1021/cr068435d, PMid:18651778
Li Z, Brouwer C, He C. Gold catalyzed organic transformations. Chem Rev. 2008;108:3239–3265. doi:10.1021/cr068434l, PMid:18613729
Gorin DJ, Sherry BD, Toste FD. Ligand effects in homogeneous Au catalysis. Chem Rev. 2008;108:3351–3378. doi:10.1021/cr068430g, PMid:18652511, PMid:2754803
Jiménez-Núñez E, Echavarren AM. Gold-catalyzed cycloisomerizations of enynes: A mechanistic perspective. Chem Rev. 2008;108:3326–3350. doi:10.1021/cr0684319, PMid:18636778
Widenhoefer RA. Recent developments in enantioselective gold(I) catalysis. Chem Eur J. 2008;14:5382–5391. doi:10.1002/chem.200800219, PMid:18442031
Belmont P, Parker E. Silver and gold catalysis for cycloisomerization reactions. Eur J Org Chem. 2009;6075–6089. doi:10.1002/ejoc.200900790
Fürstner A. Gold and platinum catalysis – a convenient tool for generating molecular complexity. Chem Soc Rev. 2009;38:3208–3221. doi:10.1039/b816696j, PMid:19847352
Nevado C. Gold catalysis: Recent developments and future trends. CHIMIA. 2010;64:247–251. doi:10.2533/chimia.2010.247
Sengupta S, Shi X. Recent advances in asymmetric gold catalysis. ChemCatChem. 2010;2:609–619. doi:10.1002/cctc.201000070
. Garcia P, Malacria M, Aubert C, Gandon V, Fensterbank L. Gold-catalysed cross-couplings: New opportunities for C–C bond formation. ChemCatChem. 2010;2:493–497. doi:10.1002/cctc.200900319
De Mendoza P, Echavarren AM. Synthesis of arenes and heteroarenes by hydroarylation reactions catalyzed by electrophilic metal complexes. Pure Appl Chem. 2010;82:801–820. doi:10.1351/PAC-CON-09-10-06
Wu J, Kroll P, Raska Dias HV. Gold(I) chloride coordinated 3-hexyne. Inorg Chem. 2009;48:423–425. doi:10.1021/ic8020854, PMid:19072612
Flügge S, Anoop A, Goddard R, Thiel W, Fürstner A. Structure and bonding in neutral and cationic 14-electron gold alkyne π-complexes. Chem Eur J. 2009;15:8558–8565. doi:10.1002/chem.200901062, PMid:19569141
Nechaev MS, Rayon VM, Frenking G. Energy partitioning analysis of the bonding in ethylene and acetylene complexes of group 6, 8 and 11 metals. J Phys Chem A. 2004;108:3134–3142. doi:10.1021/jp031185+
Garcia-Mota M, Cabello N, Maseras F, Echavarren M, Perez-Ramirez J, Lopez N. Selective homogeneous and heterogeneous gold catalysis with alkynes and alkenes: Similar behaviour and different origin. ChemPhysChem. 2008;9:1624–1629. doi:10.1002/cphc.200800246, PMid:18537219
Akana J, Bhattacharyya KX, Müller P, Sadighi J. Reversible C–F bond formation and the Au-catalyzed hydrofluorination of alkynes. J Am Chem Soc. 2007;129:7736–7737. doi:10.1021/ja0723784, PMid:17547409
Gagosz F. Recent developments in gold catalysis. Tetrahedron. 2009;65:1757–1767. doi:10.1016/j.tet.2008.12.040
Mezailles N, Ricard L, Gagosz F. Phosphine gold(I) bis(trifluoromethanesulfonyl)-imidate complexes as highly efficient and air-stable catalysts for the cycloisomerization of enynes. Org Lett. 2005;7:4133–4136. doi:10.1021/ol0515917, PMid:16146370
Hooper TN, Green M, Russell CA. Cationic Au(I) complexes: Synthesis, structure and reactivity. Chem Commun. 2010;46:2313–2315. doi:10.1039/b923900f, PMid:20234943
Hashmi SAK, Loos A, Littmann A, et al. Gold(I) complexes of KITPHOS monophosphines: Efficient cycloisomerization catalysts. Adv Synth Catal. 2009;351:576–582. doi:10.1002/adsc.200800681
Nieto-Oberhuber C, Pérez-Galán P, Herrero-Gómez E, et al. Gold(I)-catalyzed intramolecular [4 + 2] cycloadditions of arylalkynes or 1,3-enynes with alkenes: Scope and mechanism. J Am Chem Soc. 2008;130:269–279. doi:10.1021/ja075794x, PMid:18076170
Trillo B, López F, Montserrat S, et al. Gold-catalyzed [4C + 3C] intramolecular cycloaddition of allene-dienes: Synthetic protocol and mechanistic implications. Chem Eur J. 2009;15:3336–3339. doi:10.1002/chem.200900164, PMid:19229922
Mauléon P, Zeldin RM, González AZ, Toste FD. Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes. J Am Chem Soc. 2009;131:6348–6349. doi:10.1021/ja901649s, PMid:19378998, PMid:2711638
Alonso I, Trillo B, López F, et al. Gold catalyzed [4C + 2C] cycloadditions of allenedienes, including an enantioselective version with new phosphoramidite-based catalysts: Mechanistic aspects of the divergence between [4C + 3C] and [4C + 2C] pathways. J Am Chem Soc. 2009;131:13020–13030. doi:10.1021/ja905415r, PMid:19697936
Benitez D, Tkatchouk E, González AZ, Goddard (III) WA, Toste FD. On the impact of steric and electronic properties of ligands on gold(I)-catalyzed cycloaddition reactions. Org Lett. 2009;11:4798–4801. doi:10.1021/ol9018002, PMid:19780543, PMid:2783583
Alcarazo M, Stork S, Anoop A, Thiel W, Fürstner A. Steering the surprisingly modular π-acceptor properties of N-heterocyclic carbenes: Implications for gold catalysis. Angew Chem Int Ed. 2010;49:2542–2546. doi:10.1002/anie.200907194 PMid:20209549
González A, Toste FD. Gold(I)-catalyzed enantioselective [4 + 2]-cycloaddition of allene-dienes. Org Lett. 2010;12:200–203. doi:10.1021/ol902622b, PMid:19961192, PMid::2798906
Gung BW, Craft DT, Bailey LN, Kirschbaum K. Gold-catalyzed transannular [4 + 3] cycloaddition reactions. Chem Eur J. 2010;16:639–644. doi:10.1002/chem.200902185, PMid:19937623
Zeng X, Frey GD, Kinjo R, Donnadieu B, Bertrand G. Synthesis of a simplified version of stable, bulky and rigid cyclic alkyl(amino) carbenes and catalytic activity of ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives. J Am Chem Soc. 2009;131:8690–8696. doi:10.1021/ja902051m, PMid:19456108, PMid::2724870
Zeng X, Kinjo R, Donnadieu B, Bertrand G. Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes. Angew Chem Int Ed. 2010;49:942–945.
Bartholomé C, Ramiro Z, Pérez-Galán P, et al. Gold(I) complexes with hydrogen-bond supported heterocyclic carbenes as active catalysts in reactions of 1,6-enynes. Inorg Chem. 2008;47:11391–11397. doi:10.1021/ic801446v, PMid:18947178
Minghetti G, Bonati F. Bis(carbene) complexes of gold(I) and gold(III). J Organomet Chem. 1973;54:C62-C63.
Bartolomé C, Ramiro Z, Garcia-Cuadrado D, et al. Nitrogen acyclic gold(I) carbenes: Excellent and easily accessible catalysts in reactions of 1,6-enynes. Organometallics. 2010;29:951–956. doi:10.1021/om901026m
Hashmi SAK, Hengst T, Lothschütz C, Rominger F. New and easily accessible nitrogen acyclic gold(I) carbenes: Structure and application in the gold-catalyzed phenol synthesis as well as the hydration of alkynes. Adv Synth Catal. 2010;352:1315–1337. doi:10.1002/adsc.201000126
Hashmi SAK, Ramamurthi TD, Rominger F. Synthesis, structure and reactivity of organogold compounds of relevance to homogeneous gold catalysis. J Organomet Chem. 2009;694:592–597. doi:10.1016/j.jorganchem.2008.11.054
Partyka DV, Zeller M, Hunter AD, Gray TG. Relativistic functional groups: Aryl carbon-gold bond formation by selective transmetalation of boronic acids. Angew Chem Int Ed. 2006;45:8188–8191. doi:10.1002/anie.200603350, PMid:17111449
Liu L-P, Hammond GB. Reactions of cationic gold(I) with allenoates: Synthesis of stable organogold(I) complexes and mechanistic investigations on gold-catalyzed cyclizations. Chem Asian J. 2009;4:1230–1236. doi:10.1002/asia.200900091, PMid:19472292
Hashmi ASK, Lothschütz C, Döpp R, Rudolph M, Ramamarthi TD, Rominger F. Gold and palladium combined for cross-coupling. Angew Chem Int Ed. 2009;48:8243–8246. doi:10.1002/anie.200902942, PMid:19790218
Weber D, Tarselli MA, Gagné MR. Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes. Angew Chem Int Ed. 2009;48:5733–5736. doi:10.1002/anie.200902049, PMid:19562821, PMid:2978329
Cheong PH, Morganelli P, Luzung MR, Houk KN, Toste FD. Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction. J Am Chem Soc. 2008;130:4517–4526. doi:10.1021/ja711058f, PMid:18327944, PMid:2995695
Hashmi ASK, Schuster A, Rominger F. Gold catalysis: Isolation of vinylgold complexes derived from alkynes. Angew Chem Int Ed. 2009;48:8247–8249. doi:10.1002/anie.200903134, PMid:19768822
Hashmi ASK, Ramamurthi TD, Rominger F. On the trapping of vinylgold intermediates. Adv Synth Catal. 2010;352:971–975. doi:10.1002/adsc.201000011
Strasser CE, Stander-Grobler E, Schuster O, Cronje S, Raubenheimer HG. Preparation of remote NHC complexes of rhodium(I) and gold(I) by ligand transfer. Eur J Inorg Chem. 2009;1905–1912. doi:10.1002/ejic.200801180
Raubenheimer H, Cronje S. Carbene complexes of gold: Preparation, medical application and bonding. Chem Soc Rev. 2008;37:1998–2011. doi:10.1039/b708636a, PMid:18762843
Solorio-Alvarado CR, Echavarren AM. Gold-catalyzed annulation/fragmentation: Formation of free gold carbenes by retro-cyclopropanation. J Am Chem Soc. 2010;132:11881–11883. doi:10.1021/ja104743k, PMid:20698529
Binger P, Müller P, Benn R, et al. Vinylcarbene complexes of titanocene. Angew Chem Int Ed Engl. 1989;28:610–611. doi:10.1002/anie.198906101
Nguyen ST, Johnson LK, Grubbs RH. Ring-opening metathesis polymerization (ROMP) of norbornene by a group VIII carbene complex in protic media. J Am Chem Soc. 1992;114:3974–3975. doi:10.1021/ja00036a053
Seidel G, Mynott R, Fürstner A. Elementary steps of gold catalysis: NMR spectroscopy reveals the highly cationic character of a “gold carbenoid”. Angew Chem Int Ed. 2009;48:2510–2513. doi:10.1002/anie.200806059, PMid:19248070
Schuster O, Yang L, Raubenheimer HG, Albrecht M. Beyond conventional N-heterocyclic carbenes: Abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization. Chem Rev. 2009;109:3445–3478. doi:10.1021/cr8005087, PMid:19331408
Raubenheimer HG, Esterhuysen MW, Timoshkin A, Chen Y, Frenking G. Electrophilic addition of Ph3PAu+ to anionic alkoxy Fischer-type carbene complexes: A novel approach to metal stabilised bimetallic vinyl ether complexes. Organometallics. 2002;21:3173–3181. doi:10.1021/om020048g,
Raubenheimer HG, Esterhuysen MW, Frenking G, et al. Aurolysis of a-C-deprotonated group 6 aminocarbene and thiocarbene complexes with Ph3PAu+. Dalton Trans. 2006; 4580–4589. doi:10.1039/b607613k, PMid:17016569
Fürstner A, Morency L. On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions. Angew Chem Int Ed. 2008;47:5030–5033. doi:10.1002/anie.200800934, PMid:18504793
Hashmi SAK. “High noon” in gold catalysis: Carbene versus carbocation intermediates. Angew Chem Int Ed. 2008;47:6754–6756. doi:10.1002/anie.200802517, PMid:18683174
Roth KE, Blum S. Relative kinetic basicities of organogold compounds. Organometallics. 2010;29:1712–1716. doi:10.1021/om901101f
Smith MB, March J. March’s advanced organic chemistry: Reactions, mechanisms and structure. 5th ed. New York: John Wiley & Sons, 2001; p. 329.
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