Gold coordination during homogeneous alkyne and allene cyclisation catalysis: Coordination to substrates, to ancillary ligands and in intermediates
Keywords:
gold catalysts, gold complex intermediates, homogeneous catalysis, mechanistic studies, organic synthesis
Abstract
The ever-increasing role of homogeneous gold catalysis in organic synthesis and the consequent need to be able to rationally control the rate and outcome of such reactions has emphasised the importance of each successive metal–carbon coordination step. Concentrating on alkyne and allene cyclisation and upon reaction mechanisms postulated on the basis of empirical and theoretical results, we have examined the coordination of gold fragments to triple bonds, the modification of gold(I) precatalysts to effect specific reaction pathways or enantioselectivity and the isolation of coordinated intermediates or model compounds thereof. Some of the recent advances that have been made in various laboratories are described in this compact review.References
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3. 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
4. Gorin DJ, Toste FD. Relativistic effects in homogeneous gold catalysis. Nature. 2007;446:395–403. doi:10.1038/nature05592, PMid:17377576
5. Hashmi ASK. Gold catalyzed organic reactions. Chem Rev. 2007;107:3180–3211. doi:10.1021/cr000436x, PMid:17580975
6. Arcadi A. Alternative synthetic methods through new developments in catalysis by gold. Chem Rev. 2008;108:3266–3325. doi:10.1021/cr068435d, PMid:18651778
7. Li Z, Brouwer C, He C. Gold catalyzed organic transformations. Chem Rev. 2008;108:3239–3265. doi:10.1021/cr068434l, PMid:18613729
8. 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
9. 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
10. Widenhoefer RA. Recent developments in enantioselective gold(I) catalysis. Chem Eur J. 2008;14:5382–5391. doi:10.1002/chem.200800219, PMid:18442031
11. Belmont P, Parker E. Silver and gold catalysis for cycloisomerization reactions. Eur J Org Chem. 2009;6075–6089. doi:10.1002/ejoc.200900790
12. 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
13. Nevado C. Gold catalysis: Recent developments and future trends. CHIMIA. 2010;64:247–251. doi:10.2533/chimia.2010.247
14. Sengupta S, Shi X. Recent advances in asymmetric gold catalysis. ChemCatChem. 2010;2:609–619. doi:10.1002/cctc.201000070
15.. 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
16. 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
17. 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
18. 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
19. 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+
20. 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
21. 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
22. Gagosz F. Recent developments in gold catalysis. Tetrahedron. 2009;65:1757–1767. doi:10.1016/j.tet.2008.12.040
23. 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
24. 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
25. 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
26. 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
27. 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
28. 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
29. 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
30. 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
31. 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
32. 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
33. 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
34. 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
35. 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.
36. 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
37. Minghetti G, Bonati F. Bis(carbene) complexes of gold(I) and gold(III). J Organomet Chem. 1973;54:C62-C63.
38. 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
39. 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
40. 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
41. 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
42. 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
43. 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
44. 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
45. 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
46. 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
47. Hashmi ASK, Ramamurthi TD, Rominger F. On the trapping of vinylgold intermediates. Adv Synth Catal. 2010;352:971–975. doi:10.1002/adsc.201000011
48. 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
49. 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
50. 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
51. 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
52. 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
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Published
2011-03-16
Section
Review Articles