Hydroacylation of 2-butyne from the alcohol or aldehyde oxidation level via ruthenium catalyzed C-C bond forming transfer hydrogenation

Tetrahedron

Volumn 65, Issue 26, 2009, Pages 5024-5029

  Williams, Vanessa M ^a   Leung, Joyce C ^a   Patman, Ryan L ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTYNE; ACETYLENE DERIVATIVE; ALCOHOL; ALDEHYDE; ALKYNE DERIVATIVE; CARBON; KETONE; RUTHENIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENATION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 65749112195     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.068     Document Type: Article

References (85)

1. For selected reviews on metal catalyzed hydroacylation, see:
2. Bosnich B. Acc. Chem. Res. 31 (1998) 667
3. Jun C.-H., Hong J.-B., and Lee D.-Y. Synlett (1999) 1
4. Tanaka M., Sakai K., and Suemune H. Curr. Org. Chem. 7 (2003) 353
5. Fu G.C. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005) Chapter 7, pp 79-91
6. Jun C.-H., Jo E.A., and Park J.-W. Eur. J. Org. Chem. (2007) 1869
7. For rhodium-catalyzed aldehyde decarbonylation, see:
8. Doughty D.H., and Pignolet L.H. J. Am. Chem. Soc. 100 (1978) 7083
9. O'Conner J.M., and Ma J. J. Org. Chem. 57 (1992) 5075
10. Beck C.M., Rathmill S.E., Park Y.J., Chen J., and Crabtree R.H. Organometallics 18 (1999) 5311
11. For certain substrate combinations, efficient intermolecular rhodium catalyzed alkene hydroacylation is observed in the absence of β-chelation:
12. Marder T.B., Roe D.C., and Milstein D. Organometallics 7 (1988) 1451
13. Tanaka K., Shibata Y., Suda T., Hagiwara Y., and Hirano M. Org. Lett. 9 (2007) 1215
14. Roy A.H., Lenges C.P., and Brookhart M. J. Am. Chem. Soc. 129 (2007) 2082
15. Efficient intermolecular Rh-catalyzed alkene hydroacylation employing anhydrides as acyl donors and hydrogen as terminal reductant is observed in the absence of β-chelation:. Hong Y.-T., Barchuk A., and Krische M.J. Angew. Chem., Int. Ed. 128 (2006) 6885
16. For chelation-assisted intermolecular Rh-catalyzed alkene hydroacylation, see:
17. γ,δ-unsaturated aldehydes:. Vora K.P., Lochow C.F., and Miller R.G. J. Organomet. Chem. 192 (1980) 257
18. Salicylaldehydes:. Tanaka M., Imai M., Yamamoto Y., Tanaka K., Shimowatari M., Nagumo S., Kawahara N., and Suemune H. Org. Lett. 5 (2003) 1365
19. Imai M., Tanaka M., Tanaka K., Yamamoto Y., Imai-Ogata N., Shimowatari M., Nagumo S., Kawahara N., and Suemune H. J. Org. Chem. 69 (2004) 1144
20. Tanaka K., Tanaka M., and Suemune H. Tetrahedron Lett. 46 (2005) 6053
21. Imai M., Tanaka M., Nagumo S., Kawahara N., and Suemune H. J. Org. Chem. 72 (2007) 2543
22. β-sulfido-aldehyde:. Willis M.C., McNally S.J., and Beswick P.J. Angew. Chem., Int. Ed. 43 (2004) 340 Also see Refs. 9c-e,g
23. (N-2-pyridyl)aldimines:. Suggs J.W. J. Am. Chem. Soc. 101 (1979) 489
24. Jun C.-H., Lee H., and Hong J.-B. J. Org. Chem. 62 (1997) 1200
25. Jun C.-H., Lee D.-Y., Lee H., and Hong J.-B. Angew. Chem., Int. Ed. 39 (2000) 3070
26. Jun C.-H., Chung J.-W., Lee D.-Y., Loupy A., and Chatti S. Tetrahedron Lett. 42 (2001) 4803
27. Willis M.C., and Sapmaz S. Chem. Commun. (2001) 2558
28. Yańez X., Claver C., Castillon S., and Fernandez E. Tetrahedron Lett. 44 (2003) 1631
29. Efficient intermolecular cobalt catalyzed hydroacylation is restricted to the use of vinyl silanes as coupling partners:
30. Lenges C.P., and Brookhart M. J. Am. Chem. Soc. 119 (1997) 3165
31. Lenges C.P., White P.S., and Brookhart M. J. Am. Chem. Soc. 120 (1998) 6965
32. Intermolecular Ru-catalyzed hydroacylation generally requires exceptionally high reaction temperatures and provides mixtures of linear and branched coupling products:
33. Isnard P., Denise B., Sneeden R.P.A., Cognion J.M., and Durual P. J. Organomet. Chem. 240 (1982) 285
34. Isnard P., Denise B., Sneeden R.P.A., Cognion J.M., and Durual P. J. Organomet. Chem. 256 (1983) 135
35. Kondo T., Tsuji Y., and Watanabe Y. Tetrahedron Lett. 28 (1987) 6229
36. Kondo T., Akazome M., Tsuji Y., and Watanabe Y. J. Org. Chem. 55 (1990) 1286
37. Kondo T., Hiraishi N., Morisaki Y., Wada K., Watanabe Y., and Mitsudo T.-A. Organometallics 17 (1998) 2131
38. For intramolecular rhodium catalyzed alkyne hydroacylation, see:
39. Fu G.C., and Tanaka K. J. Am. Chem. Soc. 123 (2001) 11492
40. Fu G.C., and Tanaka K. Angew. Chem., Int. Ed. 41 (2002) 1607
41. Fu G.C., and Tanaka K. J. Am. Chem. Soc. 124 (2002) 10296
42. Bendorf H.D., Colella C.M., Dixon E.C., Marchetti M., Matukonis A.N., Musselman J.D., and Tiley T.A. Tetrahedron Lett. 43 (2002) 7031
43. Fu G.C., and Tanaka K. J. Am. Chem. Soc. 125 (2003) 8078
44. Takeishi K., Sugishima K., Sasaki K., and Tanaka K. Chem.-Eur. J. 10 (2004) 5681
45. Tanaka K., Sasaki K., Takeishi K., and Hirano M. Eur. J. Org. Chem. (2007) 5675
46. For chelation-assisted intermolecular alkyne hydroacylation, see:
47. Kokubo K., Matsumasa K., Miura M., and Nomura M. J. Org. Chem. 62 (1997) 4564
48. Jun C.-H., Lee H., Hong J.-B., and Kwon B.-I. Angew. Chem., Int. Ed. 41 (2002) 2146
49. Willis M.C., Randell-Sly H.E., Woodward R.L., and Currie G.S. Org. Lett. 7 (2005) 2249
50. Moxham G.L., Randell-Sly H.E., Brayshaw S.K., Woodward R.L., Weller A.S., and Willis M.C. Angew. Chem., Int. Ed. 45 (2006) 7618
51. Willis M.C., Randell-Sly H.E., Woodward R.L., McNally S., and Currie G.S. J. Org. Chem. 71 (2006) 5291
52. Rueda X.Y., and Castillon S. J. Organomet. Chem. 692 (2007) 1628
53. Moxham G.L., Randell-Sly H.E., Brayshaw S.K., Weller A.S., and Willis M.C. Chem.-Eur. J. 14 (2008) 8383
54. There exists an example of Ni-catalyzed intermolecular alkyne hydroacylation that does not require chelation-assistance, however, incomplete regio- and E/Z-stereoselectivity is observed:. Tsuda T., Kiyoi T., and Saegusa T. J. Org. Chem. 55 (1990) 2554
55. For Ru-catalyzed C-C bond forming transfer hydrogenation, see:
56. Shibahara F., Bower J.F., and Krische M.J. J. Am. Chem. Soc. 130 (2008) 6338
57. Shibahara F., Bower J.F., and Krische M.J. J. Am. Chem. Soc. 130 (2008) 14120
58. Ngai M.-Y., Skucas E., and Krische M.J. Org. Lett. 10 (2008) 2705
59. Patman R.L., Williams V.M., Bower J.F., and Krische M.J. Angew. Chem., Int. Ed. 47 (2008) 5220
60. Patman R.L., Chaulagain M.R., Williams V.M., and Krische M.J. J. Am. Chem. Soc. 131 (2009) 2066
61. For reviews encompassing Ru-catalyzed C-C bond forming transfer hydrogenation, see:
62. Shibahara F., and Krische M.J. Chem. Lett. 37 (2008) 1102
63. Bower J.F., Kim I.S., Patman R.L., and Krische M.J. Angew. Chem., Int. Ed. 48 (2009) 34
64. For recent reviews of conventional hydrogen auto-transfer processes, see:
65. Guillena G., Ramòn D.J., and Yus M. Angew. Chem., Int. Ed. 46 (2007) 2358
66. Hamid M.H.S.A., Slatford P.A., and Williams J.M.J. Adv. Synth. Catal. 349 (2007) 1555
67. For selected examples of nickel catalyzed alkyne-carbonyl reductive coupling, see:
68. Oblinger E., and Montgomery J. J. Am. Chem. Soc. 119 (1997) 9065
69. Tang X.-Q., and Montgomery J. J. Am. Chem. Soc. 121 (1999) 6098
70. Tang X.-Q., and Montgomery J. J. Am. Chem. Soc. 122 (2000) 6950
71. Huang W.-S., Chan J., and Jamison T.F. Org. Lett. 2 (2000) 4221
72. Miller K.M., Huang W.-S., and Jamison T.F. J. Am. Chem. Soc. 125 (2003) 3442
73. Takai K., Sakamoto S., and Isshiki T. Org. Lett. 5 (2003) 653
74. Mahandru G.M., Liu G., and Montgomery J. J. Am. Chem. Soc. 126 (2004) 3698
75. Knapp-Reed B., Mahandru G.M., and Montgomery J. J. Am. Chem. Soc. 127 (2005) 13156
76. For amine-unsaturated C-C coupling (hydroaminoalkylation), see:
77. Maspero F., and Clerici M.G. Synthesis (1980) 305
78. Nugent W.A., Ovenall D.W., and Homes S.J. Organometallics 2 (1983) 161
79. Herzon S.B., and Hartwig J.F. J. Am. Chem. Soc. 129 (2007) 6690
80. Herzon S.B., and Hartwig J.F. J. Am. Chem. Soc. 130 (2008) 14940
81. Kubiak R., Prochnow I., and Doye S. Angew. Chem., Int. Ed. 48 (2009) 1153
82. Bexrud J.A., Eisenberger P., Leitch D.C., Payne P.R., and Schafer L.L. J. Am. Chem. Soc. 131 (2009) 2116
83. Dobson A., Robinson S.D., and Uttley M.F. J. Chem. Soc., Dalton Trans. (1975) 370
84. Alonso F., Osanto I., and Yus M. Tetrahedron 63 (2006) 93
85. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923