Abstract
The use of gold-complexes to activate carbon–carbon π-bonds has become a well-known and highly reliable mode of reactivity for applications in organic synthesis. This review covers the use of gold-catalysts for activation of unsaturated alcohols to effect substitution with concomitant loss of water and is mostly focused on reactions where the π-acidity appears to overcome the inherent Lewis acidity of the complexes for alcohol activation. Select examples from the literature which demonstrate advances made between 2011 and 2014 are presented.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Hashmi ASK, Hutchings GJ (2006) Angew Chem Int Ed 45:7896–7936
Shapiro ND, Toste FD (2010) Synlett 5:675–691
Hashmi ASK (2014) Acc Chem Res 47:864–876
Zhang L (2014) Acc Chem Res 47:877–888
Wang Y-M, Lackner AD, Toste FD (2014) Acc Chem Res 47:889–901
Obradors C, Echavarren AM (2014) Acc Chem Res 47:902–912
Fensterbank L, Malacria M (2014) Acc Chem Res 47:953–965
Hashmi ASK (2013) Top Organomet Chem 44:143–164
Corma A, Leyva-Pérez A, Sabater MJ (2011) Chem Rev 111:1657–1712
Gorin DJ, Toste FD (2007) Nature 446:395–403
Teles JH, Brode S, Chabanas M (1998) Angew Chem Int Ed 37:1415–1417
Prati L, Rossi M (1998) J Catal 176:552–560
Fürstner A, Davies PW (2007) Angew Chem Int Ed 46:3410–3449
Fürstner A (2009) Chem Soc Rev 38:3208–3221
Fürstner A (2014) Acc Chem Res 47:925–938
Biannic B, Aponick A (2011) Eur J Org Chem 6605–6617
Muzart J (2008) Tetrahedron 64:5815–5849
Bandini M (2011) Chem Soc Rev 40:1358–1367
Rudolph M, Hashmi ASK (2012) Chem Soc Rev 41:2448–2462
Winter C, Krause N (2011) Chem Rev 111:1994–2009
Yang C-G, He C (2005) J Am Chem Soc 127:6966–6967
Liu L-P, Hammond GB (2012) Chem Soc Rev 41:3129–3139
Lalonde RL, Brenzovich WE Jr, Benitez D, Tkatchouk E, Keley K, Goddard WA III, Toste FD (2010) Chem Sci 1:226–233
Ketcham JM, Biannic B, Aponick A (2013) Chem Commun 49:4157–4159
Gómez-Suárez A, Gasperini D, Vummaleti SVC, Poater A, Cavallo L, Nolan SP (2014) ACS Catal 4:2701–2705
Aponick A, Li C-Y, Biannic B (2008) Org Lett 10:669–671
Ketcham JM, Aponick A (2013) Top Heterocycl Chem 32:157–186
Hirai Y, Terada T, Amemiya Y, Momose T (1992) Tetrahedron Lett 33:7893–7894
Debleds O, Gayon E, Vrancken E, Campagne J-M (2011) Beilstein J Org Chem 7:866–877
Mukherjee P, Widenhoefer RA (2010) Org Lett 12:1184–1187
Bandini M, Eichholzer A (2009) Angew Chem Int Ed 121:9697–9701
Unsworth WP, Stevens K, Lamont SG, Robertson J (2011) Chem Commun 47:7659–7661
Mukherjee P, Widenhoefer RA (2012) Angew Chem Int Ed 51:1405–1407
Ghebreghiorgis T, Biannic B, Kirk BH, Ess DH, Aponick A (2012) J Am Chem Soc 134:16307–16318
Mukherjee P, Widenhoefer RA (2011) Org Lett 13:1334–1337
Bandini M, Bottoni A, Chiarucci M, Cera G, Miscione GP (2012) J Am Chem Soc 134:20690–20700
Aponick A, Biannic B (2011) Org Lett 13:1330–1333
Chiarucci M, Mocci R, Syntrivanis L-D, Cera G, Mazzanti A, Bandini M (2013) Angew Chem Int Ed 52:10850–10853
Palmes JA, Paioti PHS, de Souza LP, Aponick A (2013) Chem Eur J 19:11613–11621
Palmes JA, Aponick A (2012) Synthesis 44:3699–3721
Brimble MA, Stubbing LA (2014) Top Heterocycl Chem 35:189–267
Borrero N, Aponick A (2012) J Org Chem 77:8410–8416
Thansandote P, Lautens M (2009) Chem Eur J 15:5874–5883
Ketcham JM, Cardoso FSP, Biannic B, Piras H, Aponick A (2013) Isr J Chem 53:1–9
Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471–5569
Chiarucci M, di Lillo M, Romaniello A, Cozzi PG, Cera G, Bandini M (2012) Chem Sci 3:2859–2863
Trost BM (2004) J Org Chem 69:5813–5837
Evans PA, Leahy DK, Andrews JW, Uraguchi D (2004) Angew Chem Int Ed 43:4788–4791
Onitsuka K, Okuda H, Sasai H (2008) Angew Chem Int Ed 47:1454–1457
Ueno S, Hartwig JF (2008) Angew Chem Int Ed 47:1928–1931
Roggen M, Carreira EM (2011) Angew Chem Int Ed 50:5568–5571
Young PC, Schopf NA, Lee A-L (2013) Chem Commun 49:4262–4264
Mukherjee P, Widenhoefer RA (2013) Chem Eur J 19:3437–3444
Biannic B, Ghebreghiorgis T, Aponick A (2011) Beilstein J Org Chem 7:802–807
Coutant E, Young PC, Barker G, Lee A-L (2013) Beilstein J Org Chem 9:1797–1806
Wright JR, Young PC, Lucas NT, Lee A-L, Crowley JD (2013) Organometallics 32:7065–7076
Valderas C, de la Torre MC, Fernandéz I, Muñoz MP, Sierra MA (2013) Organometallics 32:951–956
Aponick A, Li C-Y, Malinge J, Marques EF (2009) Org Lett 11:4624–4627
Egi M, Azechi K, Akai S (2009) Org Lett 11:5002–5005
Aponick A, Li C-Y, Palmes JA (2009) Org Lett 11:121–124
Chiarucci M, Matteucci E, Cera G, Fabrizi G, Bandini M (2013) Chem Asian J 8:1776–1779
Minkler SRK, Isley NA, Lippincott DJ, Krause N, Lipshutz BH (2014) Org Lett 16:724–726
Manabe K, Iimura S, Sun X-M, Kobayashi S (2002) J Am Chem Soc 124:11971–11978
Krasovskiy A, Duplais C, Lipshutz BH (2009) J Am Chem Soc 131:15592–15593
Spina R, Colacino E, Martinez G, Lamaty F (2013) Chem Eur J 19:3817–3821
Zhu L, Luo J, Hong R (2014) Org Lett 16:2162–2165
Fischbach MA, Clardy J (2007) Nat Chem Biol 3:353–355
Teo WT, Rao W, Koh MJ, Chan PWH (2013) J Org Chem 78:7508–7517
Teo WT, Rao W, Ng CJH, Koh SWY, Chan PWH (2014) Org Lett 16:1248–1351
Frantz DE, Fassler R, Carreira EM (2000) J Am Chem Soc 122:1806–1807
Xu C-F, Xu M, Yang L-Q, Li C-Y (2012) J Org Chem 77:3010–3016
Georgy M, Boucard V, Campagne JM (2005) J Am Chem Soc 127:14180–14181
Liu J, Muth E, Florke U, Henkel G, Merz K, Sauvageau J, Schwake E, Dyker G (2006) Adv Synth Catal 348:456–462
Hikawa H, Suzuki H, Azumaya I (2013) J Org Chem 78:12128–12135
Hikawa H, Suzuki H, Yokoyama Y, Azumaya I (2013) J Org Chem 78:6714–6720
Chénard E, Hanessian S (2014) Org Lett 16:2668–2671
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Paioti, P.H.S., Aponick, A. (2014). Gold-Catalyzed Transformation of Unsaturated Alcohols. In: Slaughter, L. (eds) Homogeneous Gold Catalysis. Topics in Current Chemistry, vol 357. Springer, Cham. https://doi.org/10.1007/128_2014_590
Download citation
DOI: https://doi.org/10.1007/128_2014_590
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)