Bond activation by metal-ligand cooperation: Design of "green" catalytic reactions based on aromatization-dearomatization of pincer complexes

Topics in Organometallic Chemistry

Volumn 37, Issue , 2011, Pages 55-84

  Gunanathan, Chidambaram ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Alcohols; Amides; Amines; Carbon dioxide; Catalysis; Dehydrogenative coupling; Esters; Hydrogen; Imines; Iridium; Metal ligand cooperation; O H activation; Pincer complexes; PNN; PNP; Ruthenium

Indexed keywords

EID: 79960701632     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_2011_6     Document Type: Article

References (93)

1. Beller M, Bolm C (eds) (2004) Transition metals for organic synthesis. Wiley-VCH, Weinheim
2. Whittaker JW (2005) Arch Biochem Biophys 433:227
3. Peters JW, Lanzilotta WN, Lemon BJ, Seefeldt LC (1998) Science 282:1853
4. Liu Z-P, Hu P (2002) J Am Chem Soc 124:5175
5. Fan H-J, Hall MBA (2001) J Am Chem Soc 123:3828
6. Greco C, Bruschi M, De Gioia L, Ryde UA (2007) Inorg Chem 46:5911
7. Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40
8. Clapham SE, Hadzovic A, Morris RH (2004) Coord Chem Rev 248:2201
9. Ikariya T, Blacker J (2007) Acc Chem Res 40:1300
10. Grutzmacher H (2008) Angew Chem Int Ed 47:1814
11. Ikariya T, Gridnev ID (2010) Top Catal 53:894
12. Yamakawa M, Ito H, Noyori R (2000) J Am Chem Soc 122:1466
13. Noyori R, Koizumi M, Ishii D, Ohkuma T (2001) Pure Appl Chem 73:227
14. Abbel R, Abdur-Rashid K, Faatz M, Hadzovic A, Lough AJ, Morris RHA (2005) J Am Chem Soc 127:1870
15. Casey CP, Bikzhanova GA, Cui Q, Guzei IL (2005) J Am Chem Soc 127:14062
16. Rybtchinski B, Milstein D (1999) Angew Chem Int Ed 38:870
17. Jensen CM (1999) Chem Commun:2443
18. Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750
19. Vigalok A, Milstein D (2001) Acc Chem Res 34:798
20. van der Boom ME, Milstein D (2003) Chem Rev 103:1759
21. Singleton JT (2003) Tetrahedron 259:1837
22. Milstein D (2003) Pure Appl Chem 75:445
23. Rybtchinski B, Milstein D (2004) ACS Symp Ser 885:70
24. Szabo KJ (2006) Synlett:811
25. Rybtchiski B, Milstein D (2007) In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier BV, Oxford, pp 87-105, Chapter 5
26. Milstein D (2010) Top Catal 53:915
27. Kawatsura M, Hartwig JF (2001) Organometallics 20:1960
28. Stambuli JP, Stauffer SR, Shaughnessy KH, Hartwig JF (2001) J Am Chem Soc 123:2677
29. Gibson DH, Pariya C, Mashuta MS (2004) Organometallics 223:2510
30. Kloek SM, Heinekey DM, Goldberg KI (2006) Organometallics 25:3007
31. Kloek SM, Heinekey DM, Goldberg KI (2007) Angew Chem Int Ed 46:4736
32. Hanson SK, Heinekey DM, Goldberg KI (2008) Organometallics 27:1454
33. Pelczar EM, Emge TJ, Krogh-Jespersen K, Goldman AS (2008) Organometallics 27:5759
34. van der Vlugt JI, Pidko EA, Vogt D, Lutz M, Spek AL, Meetsma A (2008) Inorg Chem 47: 4442
35. Tanaka R, Yamashita M, Nazaki K (2009) J Am Chem Soc 131:14168
36. van der Vlugt JI, Siegler MA, Janssen M, Spek AL (2009) Organometallics 28:7025
37. van der Vlugt JI, Reek JNH (2009) Angew Chem Int Ed 48:8832
38. Hermann D, Gandelman M, Rozenberg H, Shimon LJW, Milstein D (2002) Organometallics 21:812
39. Ben-Ari E, Gandelman M, Rozenberg H, Shimon LJW, Milstein D (2003) J Am Chem Soc 125:4714
40. Zhang J, Gandelman M, Shimon LJW, Rozenberg H, Milstein D (2004) Organometallics 23: 4026
41. Ben-Ari E, Cohen R, Gandelman M, Shimon LJW, Martin JML, Milstein D (2006) Organometallics 25:3190
42. Zhang J, Gandelman M, Herrman D, Leitus G, Shimon LJW, Ben-David Y, Milstein D (2006) Inorg Chim Acta 359:1955
43. Feller M, Karton A, Leitus G, Martin JML, Milstein D (2006) J Am Chem Soc 128:12400
44. Feller M, Ben-Ari E, Gupta T, Shimon LJW, Leitus G, Diskin-Posner Y, Weiner L, Milstein D (2007) Inorg Chem 46:10479
45. Zhang J, Gandelman M, Shimon LJW, Milstein D (2007) Dalton Trans:107
46. Zhang J, Gandelman M, Shimon LJW, Milstein D (2008) Inorg Chem 27:3526
47. Feller M, Iron MA, Shimon LJW, Diskin-Posner Y, Leitus G, Milstein D (2008) J Am Chem Soc 130:14374
48. Zang J, Gandelman M, Shimon LJW, Milstein D (2008) Organometallics 27:3526
49. Feller M, Ben-Ari E, Iron MA, Diskin-Posner Y, Leitus G, Shimon LJW, Milstein D (2010) Inorg Chem 49:1615
50. Zhang J, Leitus G, Ben-David Y, Milstein D (2005) J Am Chem Soc 127:12429
51. Zhang J, Leitus G, Ben-David Y, Milstein D (2006) Angew Chem Int Ed 45:1113
52. Gunanathan C, Ben-David Y, Milstein D (2007) Science 317:790
53. Kohl SW, Weiner L, Schwartsburd L, Konstantinovski L, Shimon LJW, Ben-David Y, Iron MA, Milstein D (2009) Science 324:74
54. Li J, Shiota Y, Yoshizawa K (2009) J Am Chem Soc 131:13584
55. Yang X, Hall MB (2010) J Am Chem Soc 132:120
56. Ben-Ari E, Leitus G, Shimon LJW, Milstein D (2006) J Am Chem Soc 128:15390
57. Iron MA, Ben-Ari E, Cohen R, Milstein D (2009) Dalton Trans:9433
58. Zeng G, Guo Y, Li S (2009) Inorg Chem 48:10257
59. Khaskin E, Iron MA, Shimon LJW, Zhang J, Milstein D (2010) J Am Chem Soc 132:8542
60. Vuzman D, Povernov E, Shimon LJW, Diskin-Posner Y, Milstein D (2008) Organometallics 27:2627
61. Blum Y, Shvo Y (1985) J Organomet Chem 282:C7
62. Murahashi S-I, Naota T, Ito K, Maeda Y, Taki H (1987) J Org Chem 52:4319
63. Watson AJA, Williams JMJ (2010) Science 329:635 (and references cited therein)
64. Zweifel T, Naubron J-V, Grutzmacher H (2009) Angew Chem Int Ed 48:559
65. Watson AJA, Maxwell AC, Williams JMJ (2009) Org Lett 11:2667
66. Nordstrom LU, Vogt H, Madsen R (2008) J Am Chem Soc 130:17672
67. Ghosh SC, Senthilkumar M, Zhang Y, Xu XY, Hong SH (2009) Adv Synth Catal 351:2643
68. Shimizu K, Ohshima K, Satsuma A (2009) Chem Eur J 15:9977
69. Zhang J, Senthilkumar M, Ghosh SC, Hong SH (2010) Angew Chem Int Ed 49:6391
70. Dam JH, Osztrovszky G, Nordstrøm LU, Madsen R (2010) Chem Eur J 16:6280
71. Zhang Y, Chen C, Ghosh SC, Li Y, Hong SH (2010) Organometallics 29:1374
72. Gnanaprakasam B, Zhang J, Milstein D (2010) Angew Chem Int Ed 48:1468
73. Gunanathan C, Milstein D (2008) Angew Chem Int Ed 47:8661
74. Gunanathan C, Shimon LJW, Milstein D (2009) J Am Chem Soc 131:3146
75. Hillebrand S, Barkowska B, Bruckmann J, Kruger C, Haenel MW (1998) Tetrahedron Lett 39:813
76. Ito T, Horino H, Koshiro Y, Yamamoto A (1982) Bull Chem Soc Jpn 55:504
77. Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB (2005) Angew Chem Int Ed 44:3275
78. Shapiro N, Vigalok A (2008) Angew Chem Int Ed 47:2849
79. Gunanathan C, Gnanaprakasam B, Iron MA, Shimon LJW, Milstein D (2010) J Am Chem Soc 132:14763
80. Ito M, Ikariya T (2007) Chem Commun:5134
81. Saudan LA, Saudan CM, Debieux C, Wyss P (2007) Angew Chem Int Ed 46:7473
82. Kuriyama W, Ino Y, Ogata O, Sayo N, Saito T (2010) Adv Synth Catal 352:92
83. Tanaka R, Yamashita M, Nozaki K (2009) J Am Chem Soc 131:14168
84. Ezhova NN, Kolesnichenko NV, Bulygin AV, Slivin-skii EV, Han S (2002) Russ Chem Bull Int Ed 51:2165
85. Graf E, Leitner W (1992) J Chem Soc Chem Commun:623
86. Gassner F, Leitner W (1993) J Chem Soc Chem Commun:1465
87. Angermund K, Baumann W, Dinjus E, Fornika R, Görls H, Kessler M, Krüger C, Leitner W, Lutz F (1997) Chem Eur J 3:755
88. Jessop PG, Ikariya T, Noyori R (1994) Nature 368:231
89. Jessop PG, Hsiao Y, Ikariya T, Noyori R (1996) J Am Chem Soc 118:344
90. Urakawa A, Jutz F, Laurenczy G, Baiker A (2007) Chem Eur J 13:3886
91. Munshi P, Main AD, Linehan JC, Tai CC, Jessop PG (2002) J Am Chem Soc 124:7963
92. Himeda Y, Onozawa-Komatsuzaki N, Sugihara H, Kasuga K (2007) Organometallics 26:702
93. Käß M, Friedrich A, Drees M, Schneider S (2009) Angew Chem Int Ed 48:905