Abstract
Gold catalysis is considered one of the most important breakthroughs in organic synthesis during the last decade. Many gold-catalyzed reactions suffer from high catalyst loading, which is a serious limitation on the application of gold catalysis in larger scale synthesis. Because ligands play a major role in the tuning of reactivity of transition metal catalysts, there has been an increased effort on rationally understanding ligand effects in gold catalysis and using a rational ligand design to achieve higher efficiency. In the first part of this chapter, selected examples of ligand design in gold catalysis are discussed. In the second part, the chemistry of gold–oxonium intermediate is examined. An oxonium intermediate is generated when a oxygen nucleophile (ketone, aldehyde, or ether) attacks a cationic gold-activated multiple bond. This oxonium intermediate, being a highly energetic species, has the potential to undergo further transformations such as electron transfer/rearrangement/protodeauration to form diverse products.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
- 1.
Cambridge Crystallographic Data Centre (CCDC) depository # 973355.
References
Liu LP, Malhotra D, Jin Z, Paton RS, Houk KN, Hammond GB (2011) Chem Eur J 17:10690
Garcia P, Malacria M, Aubert C, Gandon V, Fensterbank L (2010) ChemCatChem 2:493
Liu LP, Malhotra D, Paton RS, Houk KN, Hammond GB (2010) Angew Chem Int Ed 49:9132
Arcadi A (2008) Chem Rev 108:3266
Gorin DJ, Sherry BD, Toste FD (2008) Chem Rev 108:3351
Li Z, Brouwer C, He C (2008) Chem Rev 108:3239
Hashmi ASK (2007) Chem Rev 107:3180
Jimenez-Nunez E, Echavarren AM (2008) Chem Rev 108:3326
Hashmi ASK, Rudolph M (2008) Chem Soc Rev 37:1766
Widenhoefer RA (2008) Chem Eur J 14:5382
Rudolph M (2012) Hashmi. A. S. K. Chem. Soc, Rev
Brenzovich WE (2012) Angew Chem Int Ed 51:8933
Benitez D, Shapiro ND, Tkatchouk E, Wang Y, Goddard WA, Toste FD (2009) Nat Chem 1:482
Teles JH, Brode S, Chabanas M (1998) Angew Chem Int Ed 37:1415
Gorin DJ, Toste FD (2007) Nature 446:395
Lein M, Rudolph M, Hashmi SK, Schwerdtfeger P (2010) Organometallics 29:2206
Pernpointner M, Hashmi ASK (2009) J Chem Theory Comput 5:2717
Hertwig RH, Koch W, Schröder D, Schwarz H, Hrušák J, Schwerdtfeger P (1996) J Phys Chem 100:12253
Shen Q, Shekhar S, Stambuli JP, Hartwig JF (2005) Angew Chem Int Ed 44:1371
Fors BP, Watson DA, Biscoe MR, Buchwald SL (2008) J Am Chem Soc 130:13552
Watson DA, Su M, Teverovskiy G, Zhang Y, Garcia-Fortanet J, Kinzel T, Buchwald SL (2009) Science 325:1661
Cho EJ, Senecal TD, Kinzel T, Zhang Y, Watson DA, Buchwald SL (2010) Science 328:1679
Wang Y-M, Lackner AD, Toste FD (2014) Acc Chem Res 47:889
Wang W, Hammond GB, Xu B (2012) J Am Chem Soc 134:5697
Kumar M, Jasinski J, Hammond GB, Xu B (2014) Chem Eur J 20:3113
Brown TJ, Weber D, Gagné MR, Widenhoefer RA (2012) J Am Chem Soc 134:9134
Herrero-Gómez E, Nieto-Oberhuber C, López S, Benet-Buchholz J, Echavarren AM (2006) Angew Chem Int Ed 45:5455
Wang ZJ, Benitez D, Tkatchouk E, Goddard Iii WA, Toste FD (2010) J Am Chem Soc 132:13064
Carreras J, Gopakumar G, Gu L, Gimeno A, Linowski P, Petuškova J, Thiel W, Alcarazo M (2013) J Am Chem Soc 135:18815
Alcarazo M (2014) Chem Eur J 20:7868
Malhotra D, Mashuta MS, Hammond GB, Xu B (2014) Angew Chem Int Ed 53:4456
Gatineau D, Goddard J-P, Mouriès-Mansuy V, Fensterbank L (2013) Isr J Chem 53:892
Blanco Jaimes MC, Böhling CRN, Serrano-Becerra JM, Hashmi ASK (2013) Angew Chem Int Ed 52:7963
Lavallo V, Frey GD, Kousar S, Donnadieu B, Bertrand G (2007) Proc Natl Acad Sci U S A 104:13569
Zeng X, Kinjo R, Donnadieu B, Bertrand G (2010) Angew Chem Int Ed 49:942
Zeng X, Frey GD, Kinjo R, Donnadieu B, Bertrand G (2009) J Am Chem Soc 131:8690
Lavallo V, Wright JH, Tham FS, Quinlivan S (2013) Angew Chem Int Ed 52:3172
Wang Y, Wang Z, Li Y, Wu G, Cao Z, Zhang L (2014) Nat Commun 5, 3470
Hashmi ASK, Schwarz L, Choi J-H, Frost TM (2000) Angew Chem Int Ed 39:2285
Jin T, Yamamoto Y (2007) Org Lett 9:5259
Jin T, Yamamoto Y (2008) Org Lett 10:3137
Krafft ME, Vidhani DV, Cran JW, Manoharan M (2011) Chem Commun 47:6707
Rodríguez A, Moran WJ (2011) Tetrahedron Lett 52:2605
Li J, Liu L, Ding D, Sun J, Ji Y, Dong J (2013) Org Lett 15:2884
Asao N, Takahashi K, Lee S, Kasahara T, Yamamoto Y (2002) J Am Chem Soc 124:12650
Asao N, Aikawa H, Yamamoto Y (2004) J Am Chem Soc 126:7458
Liu L-P, Hammond GB (2010) Org Lett 12:4640
Hashmi ASK, Sinha P (2004) Adv Synth Catal 346:432
Wang T, Shi S, Vilhelmsen MH, Zhang T, Rudolph M, Rominger F, Hashmi ASK (2013) Chem Eur J 19:12512
Shu X-Z, Liu X-Y, Xiao H-Q, Ji K-G, Guo L-N, Qi C-Z, Liang Y-M (2007) Adv Synth Catal 349:2493
Ji K-G, Shu X-Z, Chen J, Zhao S-C, Zheng Z-J, Liu X-Y, Liang Y-M (2009) Org Biomol Chem 7:2501
Uemura M, Watson IDG, Katsukawa M, Toste FD (2009) J Am Chem Soc 131:3464
Renault J, Qian Z, Uriac P, Gouault N (2011) Tetrahedron Lett 52:2476
Acknowledgements
The authors are grateful to the National Science Foundation for financial support (grant CHE 1111316).
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Malhotra, D., Hammond, G.B., Xu, B. (2014). Ligand Design in Gold Catalysis and Chemistry of Gold–Oxonium Intermediates. In: Slaughter, L. (eds) Homogeneous Gold Catalysis. Topics in Current Chemistry, vol 357. Springer, Cham. https://doi.org/10.1007/128_2014_592
Download citation
DOI: https://doi.org/10.1007/128_2014_592
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-13721-6
Online ISBN: 978-3-319-13722-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)