Cluster preface: Gold catalysis for organic synthesis: Opportunities abound

Synlett

Volumn , Issue 1, 2012, Pages 46-48

  Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

acid catalyst; gold catalysis; oxidative coupling

Indexed keywords

ALCOHOL; ALKYNE; CARBENE; CARBENOID; CARBON; CATION; COUNTERION; GOLD; GOLD CHLORIDE; LEWIS ACID; LIGAND; MONOPHOSPHINE; NUCLEOPHILE; PHOSPHINE DERIVATIVE; PHOSPHINEGOLD COMPLEX; PHOSPHITE; PHOSPHORAMIDOUS ACID; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALDOL REACTION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; ENANTIOSELECTIVITY; ISOMERIZATION; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; OXIDATIVE COUPLING; REVIEW; SYNTHESIS;

EID: 84655167727     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290112     Document Type: Review

References (52)

1. Ito Y, Sawamura M, Hayashi T, J. Am. Chem. Soc. 1986 108 6405
2. For early examples of gold(III)-catalyzed C-C bond formation, see:, Hashmi A S. K., Frost T M., Bats J W., J. Am. Chem. Soc. 2000 122 11553
3. Hashmi A S. K., Frost T M., Bats J W., Org. Lett. 2001 3 3769
4. Asao N, Nogami T, Lee S, Yamamoto Y, J. Am. Chem. Soc. 2003 125 10921
5. Reetz M T., Sommer K, Eur. J. Org. Chem. 2003 3485
6. Dyker G, Muth E, Hashmi A S. K., Ding L, Adv. Synth. Catal. 2003 345 1247
7. Teles J H., Brode S, Chabanas M, Angew. Chem. Int. Ed. 1998 37 1415
8. 3P(1500). Additionally, (in ref. 16) they report that carbenegold(I) complex proved to be 3.5 times more active than triphenylphosphanegold(I) chloride
9. Kennedy-Smith J J., Staben S T., Toste F D., J. Am. Chem. Soc. 2004 126 4526
10. Nieto-Oberhuber C, Muñoz M P., Buñuel E, Nevado C, Cárdenas D J., Echavarren A M., Angew. Chem. Int. Ed. 2004 43 2402
11. Pradal, A.; Chen, Q.; FaudotditBel, P.; Toullec, P. A.; Michelet, V. Synlett 2011, DOI: 10 1055/s-0031-1289867.
12. Núria, H.; Echavarren, A. M. Synlett 2011, DOI: 10 1055/s-0031-1289532.
13. Hashmi A S. K., Rudolph M, Chem. Soc. Rev. 2008 37 1766
14. Fürstner A, Chem. Soc. Rev. 2009 38 3208
15. Mamane V, Gress T, Krause H, Fürstner A, J. Am. Chem. Soc. 2004 126 8654
16. Harrak Y, Blaszykowski C, Bernard M, Cariou K, Mainetti E, Mouriés V, Dhimane A.-L, Fensterbank L, Malacria M, J. Am. Chem. Soc. 2004 126 8656
17. Luzung M R., Markham J P., Toste F D., J. Am. Chem. Soc. 2004 126 10858
18. Rautenstrauch V, J. Org. Chem. 1984 49 950
19. Miki K, Ohe K, Uemura S, Tetrahedron Lett. 2003 44 2019
20. Miki K, Ohe K, Uemura S, J. Org. Chem. 2003 68 8505
21. Shi X, Gorin D J., Toste F D., J. Am. Chem. Soc. 2005 127 5802
22. Johansson M J., Gorin D J., Staben S T., Toste F D., J. Am. Chem. Soc. 2005 127 18002
23. Watson I D. G., Ritter S, Toste F D., J. Am. Chem. Soc. 2009 131 2056
24. Marco-Contelles J, Soriano E, Chem. Eur. J. 2007 13 1350
25. Gorin D J., Davis N R., Toste F D., J. Am. Chem. Soc. 2005 127 11260
26. Shapiro N D., Toste F D., J. Am. Chem. Soc. 2007 129 4160
27. Xiao J, Li X, Angew. Chem. Int. Ed. 2011 50 7226
28. Davies, P. W.; Albrecht, S. J.-C. Synlett 2011, DOI: 10 1055/s-0031-1289866.
29. For an example of ligand-controlled chemoselectivity, see:, Mauleón P, Zeldin R M., González A Z., Toste F D., J. Am. Chem. Soc. 2009 131 6348
30. Sengupta S, Shi X, ChemCatChem 2010 2 609
31. Pradal A, Toullec P Y., Michelet V, Synthesis 2011 1501
32. Martín-Rodríguez M, Nájera C, Sansano J M., Synlett, 2011 DOI: 10 1055/s-0030-1260334
33. Melhado A D., Luparia M, Toste F D., J. Am. Chem. Soc. 2007 129 12638
34. Hamilton G L., Kang E J., Miriam M, Toste F D., Science 2007 317 496
35. LaLonde R L., Wang Z J., Mba M, Lackner A D., Toste F D., Angew. Chem. Int. Ed. 2010 49 598
36. Kojima, M.; Mikami, K. Synlett 2011, DOI: 10 1055/s-0031-1289875.
37. Campbell M J., Toste F D., Chem. Sci. 2011 2 1369
38. González A Z., Toste F D., Org. Lett. 2010 12 200
39. Alonso I, Trillo B, López F, Montserrat S, Ujaque G, Castedo L, Lledós A, Mascareñas J L., J. Am. Chem. Soc. 2009 131 13020
40. Teller H, Flugge S, Goddard R, Fürstner A, Angew. Chem. Int. Ed. 2010 49 1949
41. González A Z., Benitez D, Tkatchouk E, Goddard W A. III., W A, Toste F D., J. Am. Chem. Soc. 2011 133 5500
42. Wang Y.-M, Kuzniewski C N., Rauniyar V, Hoong C, Toste F D., J. Am. Chem. Soc. 2011 133 19972; and references cited therein
43. Hopkinson M N., Gee A D., Gouverneur V, Chem. Eur J. 2011 30 8248
44. Cheon C H., Kanno O, Toste F D., J. Am. Chem. Soc. 2011 133 13248
45. Hashmi A S. K., Hubbert C, Angew. Chem. Int. Ed. 2010 49 1010
46. Loh C C. J., Badorrek J, Raabe G, Enders D, Chem. Eur. J. 2011 DOI: 10 1002/chem. 201102793
47. Shi Y, Roth K, Ramgren S D., Blum S A., J. Am. Chem. Soc. 2009 131 18022
48. Cavarzan A, Scarso A, Sgarbossa P, Strukul G, Reek J N. H., J. Am. Chem. Soc. 2011 133 2848
49. Wang Z J., Brown C J., Bergman R G., Raymond K N., Toste F D., J. Am. Chem. Soc. 2011 133 7359
50. Asao N, Menggenbateer, Seya Y, Yamamoto Y, Chen M, Zhang W, Inoue A, Synlett 2011 DOI: 10 1055/s-0031-1289527
51. Zhang X, Xamena L, Corma A, J. Catal. 2009 265 155
52. Yoo W.-J, Miyamura H, Kobayashi S, J. Am. Chem. Soc. 2011 133 3095