Isomerization-hydroformylation tandem reactions

ACS Catalysis

Volumn 4, Issue 6, 2014, Pages 1706-1724

  Vilches Herrera, Marcelo ^a   Domke, Lutz ^a   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

hydroformylation; isomerization; tandem catalysis

Indexed keywords

CATALYSIS; ISOMERIZATION; ISOMERS; RUTHENIUM;

ALKYL CHAIN; DOUBLE BONDS; LINEAR ALDEHYDES; METAL-CATALYZED; PHOSPHORUS LIGANDS; TANDEM CATALYSIS; TANDEM REACTION; TERMINAL POSITION;

HYDROFORMYLATION;

EID: 84902203402     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs500273d     Document Type: Review

References (237)

1. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, Ch. W. J. Mol. Catal. A: Chem. 1995, 104, 17-85
2. Rhodium Catalyzed Hydroformylation; van Leeuwen, P. W. N. M.; Claver, C., Eds.; Kluver Academic Publishers: Dordrecht, Netherlands, 2000.
3. Franke, R.; Selent, D.; Börner, A. Chem. Rev. 2012, 112, 5675-5732
4. Whiteker, G. T.; Cobley, C. J. Top. Organomet. Chem. 2012, 42, 35-46
5. Gusevskaya, E. V.; Jiménez-Pinto, J.; Börner, A. ChemCatChem. 2014, 6, 382-411
6. Pospech, J.; Fleischer, I.; Franke, R.; Buchholz, S.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 2852-2872
7. Phosphorus(III) Ligands in Homogeneous Catalysis; Kamer, P. C. J.; van Leeuwen, P. W. N. M., Eds.; Wiley: Chichester, UK, 2012.
8. Gil, W.; Boczoń, K.; Trzeciak, A. M.; Ziołkowski, J. J.; Garcia-Verdugo, E.; Luis, S. V.; Sans, V. J. Mol. Catal. A: Chem. 2009, 309, 131-136
9. Dastgir, S.; Coleman, K. S.; Green, M. L. H. Dalton Trans. 2011, 40, 661-672
10. Clearly, also terminal olefins can isomerize prior to the hydroformylation. For n-regioselective hydroformylation, the catalyst must display activity for isomerization as well as for hydroformylation, as shown with 10-undecenenitril as substrate: Ternel, J.; Couturier, J.-L.; Dubois, J.-L.; Carpentier, J.-F. Adv. Synth. Catal. 2013, 355, 3191-3204
11. Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001-1020
12. Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365-2379
13. Ungvary, F. Coord. Chem. Rev.; Regular annual survey on hydroformylation reactions.
14. Eilbracht, P.; Bärfacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329-3365
15. Eilbracht, P.; Schmidt, A. M. In Transition Metal for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 57-85.
16. Eilbracht, P.; Schmidt, A. M. Top. Organomet. Chem. 2006, 18, 65-95
17. Breit, B. Acc. Chem. Res. 2003, 36, 264-275
18. Behr, A.; Vorholt, A. J. Top. Organomet. Chem. 2012, 39, 103-128
19. Behr, A.; Vorholt, A. J.; Ostrowski, K. A.; Seidensticker, T. Green Chem. 2014, 16, 982-1006
20. 75 Years of Oxo Synthesis; Frey, G.; Dämbkes, G., Eds.; Oxea GmbH, Klartext Verlag: Essen, Germany, 2013.
21. See, for example: Baber, R. A.; Haddow, M. F.; Middleton, A. J.; Orpen, A. G.; Pringle, P. G.; Haynes, A.; Williams, G. L.; Papp, R. Organometallics 2007, 26, 713-725
22. For recent investigations of the mechanism, see, for example: Nelsen, E. R.; Landis, C. R. J. Am. Chem. Soc. 2013, 135, 9636-9639
23. It should be noted that nonisomerizing n-regioselective hydroformylation, for example, of butene mixtures, can be used as a method to separate the terminal from the internal olefins: Kreidler, B.; Wiese, K.-D.; Hess, D.; Selent, D.; Boerner, A. Evonik Oxeno G.m.b.H; German Patent DE 102008002188, 2009; Chem. Abstr. 2009, 152, 37087.
24. Parshall, G. W. Homogeneous Catalysis; Wiley: New York, 1980; Chapter 3.
25. Orchin, M. In Adv. Catal. Eley, D. D.; Pines, H.; Weisz, P. B., Eds.; Academic Press: New York, 1966; Vol. 16, pp 1-47.
26. Chaloner, P. A. Handbook of Coordination Catalysis in Organic Chemistry; Butterworths: London, UK, 1986; Chapter 5.
27. van Leeuwen, P. W. N. M. Homogeneous Catalysis-Understanding the Art; Kluwer Academic Publishers: Dordrecht, Netherlands, 2004; pp 101-107.
28. Otsuka, S.; Tani, K. In Transition Metal for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 199-209.
29. A further type of mechanism is the isomerization of allylamines or allyl alcohols: Inoue, S.-i.; Takaya, H.; Otsuka, S.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 4897-4905
30. Tolman, C. A. J. Am. Chem. Soc. 1972, 94, 2994-2999
31. Hendrix, W. T.; von Rosenberg, J. L. J. Am. Chem. Soc. 1976, 98, 4850-4852
32. Casey, C. P.; Cyr, C. R. J. Am. Chem. Soc. 1973, 95, 2248-2253
33. Morrill, T. C.; D'Souza, Ch. A. Organometallics 2003, 22, 1626-1629 and references cited therein
34. Bingham, D.; Hudson, B.; Webster, D. E.; Wells, P. B. J. Chem. Soc., Dalton Trans. 1974, 1521-1524
35. Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1966, 88, 3491-3497
36. Stefani, A.; Consiglio, G.; Botteghi, C.; Pino, P. J. Am. Chem. Soc. 1977, 99, 1058-1063
37. Orchin, M.; Rupilius, W. Catal. Rev. Sci. Eng. 1972, 6, 85-131
38. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081-3089
39. Bingham, D.; Webster, D. E.; Wells, P. B. J. Chem. Soc., Dalton Trans. 1974, 1514-1518
40. Bingham, D.; Webster, D. E.; Wells, P. B. J. Chem. Soc., Dalton Trans. 1974, 1519-1521
41. Selent, D.; Franke, R.; Kubis, Ch.; Spannenberg, A.; Baumann, W.; Kreidler, B.; Börner, A. Organometallics 2011, 30, 4509-4514
42. Chen, C.; Dugan, T. R.; Brennessel, W. W.; Weix, D. J.; Holland, P. L. J. Am. Chem. Soc. 2014, 136, 945-955 and references cited therein
43. Behr, A.; Obst, D.; Westfechtel, A. Eur. J. Lipid. Sci. Technol. 2005, 107, 213-219
44. DeJarlais, W. J.; Gast, L. E. J. Am. Oil Chem. Soc. 1971, 48, 21-24
45. Andjelkovic, D. D.; Min, B.; Ahn, D.; Larock, R. C. J. Agric. Food Chem. 2006, 54, 9535-9543
46. Behr, A.; Witte, H.; Bayrak, Z. Eur. J. Lipid. Sci. Technol. 2013, 115, 721-728
47. Bailar, J. C., Jr.; Itatani, H. J. Am. Chem. Soc. 1967, 89, 1592-1599
48. Fell, B.; Bahrmann, H. J. Mol. Catal. 1980, 8, 329-337
49. Fell, B.; Rupilius, W. Tetrahedron Lett. 1969, 32, 2721-2723
50. Fyhr, C.; Garland, M. Organometallics 1993, 12, 1753-1764
51. Liu, G.; Garland, M. J. Organomet. Chem. 2000, 608, 76-85
52. Wakamatsu, H.; Nishida, M.; Adachi, N.; Mori, M. J. Org. Chem. 2000, 65, 3966-4970
53. Garland, M. Organometallics 1993, 12, 535-543
54. Kubis, Ch.; Ludwig, R.; Sawall, M.; Neymeyr, K.; Börner, A.; Wiese, K.-D.; Hess, D.; Franke, R.; Selent, D. ChemCatChem 2010, 2, 287-295
55. Kubis, Ch.; Selent, D.; Sawall, M.; Ludwig, R.; Neymeyr, K.; Baumann, W.; Franke, R.; Börner, A. Chem. - Eur. J. 2012, 18, 8780-8794
56. Van der Veen, L. A.; Boele, M. D. K.; Bregman, F. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Schenk, H.; Bo, C. J. Am. Chem. Soc. 1998, 120, 11616-11626
57. Compare, for example: Cornils, B. In New Syntheses with Carbon Monoxide; Falbe, J.; Ed. Springer: Berlin, Germany, 1980; pp 1-225.
58. Moasser, B.; Gladfelter, W. L.; Roe, D. C. Organometallics 1995, 14, 3832-3838
59. Carvajal, M. A.; Kozuch, S.; Shaik, S. Organometallics 2009, 28, 3656-3665
60. Behr, A.; Obst, D.; Schulte, C. Chem. Ing. Tech. 2004, 76, 904-910
61. Cai, C.; Yu, S.; Liu, G.; Zhang, X.; Zhang, X. Adv. Synth. Catal. 2011, 353, 2665-2670
62. Smejkal, T.; Breit, B. Angew. Chem., Int. Ed. 2008, 47, 311-315
63. Smejkal, T.; Gribkov, D.; Geier, J.; Keller, M.; Breit, B. Chem. - Eur. J. 2010, 16, 2470-2478
64. Dydio, P.; Detz, R. J.; Reek, J. N. H. J. Am. Chem. Soc. 2013, 135, 10817-10828
65. Piacenti, F.; Bianchi, M.; Frediani, P.; Menchi, G.; Matteoli, U. J. Organomet. Chem. 1991, 417, 77-88
66. Consiglio, G. Organometallics 1988, 7, 778-780
67. Pino, P.; Oldani, F.; Consiglio, G. J. Organomet. Chem. 1983, 250, 491-497
68. Godard, C.; Duckett, S. B.; Polas, S.; Tooze, R.; Whitwood, A. C. Dalton Trans. 2009, 2496-2509
69. Piacenti, F.; Pucci, S.; Bianchi, M.; Lazzaroni, R.; Pino, P. J. Am. Chem. Soc. 1968, 90, 6847-6849
70. Casey, C. P.; Whiteker, G. T. Isr. J. Chem. 1990, 30, 299-304
71. Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A., Jr.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535-5543
72. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769
73. Kamer, P. C.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895-904
74. Birbeck, J. M.; Haynes, A.; Adams, H.; Damoense, L.; Otto, S. ACS Catal. 2012, 2, 2512-2523
75. Diebolt, O.; van Leeuwen, P. W. N. M.; Kamer, P. C. J. ACS Catal. 2012, 2, 2357-2370
76. Tolman, C. A. Chem. Rev. 1977, 77, 313-348
77. In a first rough calculation, the minimum energy difference for an efficient regiodiscrimination between regioisomers was determined to be >2.0 kcal/mol. This can be achieved by application of diphosphines with a bite angle of 100-160° and a Toman angle of 120-140°: Bahmann, H.; Kohlpaintner, Ch. W.; Herrmann, W. A.; Schmid, R.; Albanese, G. Hoechst AG; German Patent DE 4426577 1996; Chem. Abstr. 1996, 124, 316515.
78. Lenges, C. P.; Brookhart, M. Angew. Chem., Int. Ed. 1999, 38, 3533-3537
79. Heck, R. F.; Breslow, D. S. J. Am. Chem. Soc. 1961, 83, 4023-4027
80. Versluis, L.; Ziegler, T.; Baerends, E. J.; Ravenek, W. J. Am. Chem. Soc. 1989, 111, 2018-2025
81. Versluis, L.; Ziegler, T. Organometallics 1990, 9, 2985-2992
82. Hebrard, F.; Kalck, P. Chem. Rev. 2009, 109, 4272-4282
83. Azran, J.; Orchin, M. Organometallics 1984, 3, 197-199
84. Taube, R. Homogene Katalyse; Akademie-Verlag: Berlin, Germany, 1988; p 312.
85. Frohning, C. D.; Kohlpaintner, C. W. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; VCH: Weinheim, Germany, 1996; pp 29-104.
86. Alemdaroǧlu, N. H.; Penninger, J. M. L; Oltay, E. Monatsh. Chem. 1976, 107, 1043-1053
87. Ungváry, F. J. Organomet. Chem. 1972, 36, 363-370
88. Haymore, B. L.; van Asselt, A.; Beck, G. R. Ann. N.Y. Acad. Sci. 1983, 415, 159-175
89. Rosi, L.; Bini, A.; Frediani, P.; Bianchi, M.; Salvini, A. J. Mol. Catal. A: Chem. 1996, 112, 367-383
90. Karapinka, G. L.; Orchin, M. J. Org. Chem. 1961, 26, 4187-4190
91. Pino, P. Ann. N.Y. Acad. Sci. 1983, 415, 111-128
92. Pino, P.; Major, A.; Spindler, F.; Tannenbaum, R.; Bor, G.; Hórvath, I. T. J. Organomet. Chem. 1991, 417, 65-76
93. Tannenbaum, R.; Bor, G. J. Organomet. Chem. 1999, 586, 18-22 and references cited therein.
94. Huo, C.-F.; Li, Y.-W.; Beller, M.; Jiao, H. Organometallics 2003, 22, 4665-4677
95. Slaugh, L. H.; Mullineaux, R. D. J. Organomet. Chem. 1968, 13, 469-477
96. Fell, B.; Rupilius, W.; Asinger, F. Tetrahedron Lett. 1968, 29, 3261-3266
97. Srivastava, V. K.; Shukla, R. S.; Bajaj, H. C.; Jasra, R. V. Appl. Catal., A 2005, 282, 31-38
98. Slaugh, L. H.; Mullineaux, R. D. Shell Oil Company; U.S. Patent 3,239,569, 1966; Chem. Abstr. 1966, 64, 65101.
99. Mason, R. F.; van Winkle, J. L. Shell Oil Company; U.S. Patent 3400163, 1968; Chem. Abstr. 1974, 80, 146299.
100. Van Winkle, J. L.; Lorenzo, S.; Morris, R. C.; Mason, R. F. Shell Oil Company; U.S. Patent 3420898, 1969; Chem. Abstr. 1967, 66, 65101.
101. Bungu, P. N.; Otto, S. J. Organomet. Chem. 2007, 692, 3370-3379
102. Crause, C.; Bennie, L.; Damoense, L.; Dwyer, C. L.; Grove, C.; Grimmer, N.; Janse van Rensburg, W.; Kirk, M. M.; Mokheseng, K. M.; Otto, S.; Steynberg, P. J. J. Chem. Soc., Dalton Trans. 2003, 2036-2042
103. Polas, A.; Wilton-Ely, J. D. E. T.; Slawin, A. M. Z.; Forster, D. F.; Stynberg, P. J.; Green, M. J.; Cole-Hamilton, D. J. Dalton Trans. 2003, 4669-4677
104. Haumann, M.; Meijboom, R.; Moss, J. R.; Roodt, A. Dalton Trans. 2004, 1679-1686
105. Meijboom, R.; Haumann, M.; Roodt, A.; Damoense, L. Helv. Chim. Acta 2005, 88, 676-693
106. Kant, M.; Martin, A.; Giuffrida, G.; Rosano, S. Chem. Ing. Tech. 2006, 78, 913-921
107. Beller, M.; Krauter, J. G. E. J. Mol. Catal. A: Chem. 1999, 143, 31-39
108. Zhang, Y.; Shinoda, M.; Shiki, Y.; Tsubaki, N. Fuel 2006, 85, 1194-1200
109. Himmele, W.; Siegel, H. Tetrahedron Lett. 1976, 907-910
110. Liu, G.; Volken, R.; Garland, M. Organometallics 1999, 18, 3429-3436 and references cited therein
111. Taube, R. Homogene Katalyse; Akademie-Verlag: Berlin, Germany, 1988; p 321.
112. Lazzaroni, R.; Uccello-Barreta, G.; Benetti, M. Organometallics 1989, 8, 2323-2327
113. Dos Santos, E. N.; Pittman, C. U., Jr.; Toghiani, H. J. Mol. Catal. 1993, 83, 51-65
114. De Freitas, M. C.; Vieira, C. G.; dos Santos, E. N.; Gusevskaya, E. V. ChemCatChem 2013, 5, 1884-1890
115. Pagenelli, S.; Battois, F.; Marchetti, M.; Lazzaroni, R.; Settambolo, R.; Rocchiccioli, S. J. Mol. Catal. A: Chem. 2006, 246, 195-199
116. Himmele, W.; Siegel, H. BASF AG; GermanPatent DE 2235466, 1974; Chem. Abstr. 1974, 81, 3593.
117. Osborn, J. A.; Wilkinson, G.; Young, J. F. Chem. Commun. 1965, 17
118. Evans, D.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1968, 3133-3142
119. Carlock, J. T. Tetrahedron 1984, 40, 185-192
120. Horvath, I. T.; Kastrup, R. V.; Oswaldt, A. A.; Mozeleski, E. J. Catal. Lett. 1989, 2, 85-90
121. Bohnen, H.-W.; Cornils, B. Adv. Synth. Catal. 2002, 47, 1-64
122. Albers, J.; Dinjus, E.; Pitter, S.; Walter, O. J. Mol. Catal. A: Chem. 2004, 219, 41-46
123. Devon, T. J.; Phillips, G. W.; Puckette, T. A.; Stavinoha, J. L.; Vanderbilt, J. J. Eastman Kodak Company; U.S. Patent 4694109, 1987; Chem. Abstr. 1988, 108, 7890.
124. Tamao, K.; Yamamoto, H.; Matsumoto, H.; Miyake, N.; Hayashi, T.; Kumada, M. Tetrahedron Lett. 1977, 1389-1392
125. Devon, T. J.; Puckette, T. A.; Inoha, J. L. Eastman Kodak Company; WO Patent 87/07600, 1987; Chem. Abstr. 1988, 109, 8397.
126. Herrmann, W. A.; Schmid, R.; Kohlpaintner, C. W.; Priermeier, T. Organometallics 1995, 14, 1961-1968
127. Klein, H.; Jackstell, R.; Wiese, K.-D.; Borgmann, C.; Beller, M. Angew. Chem., Int. Ed. 2001, 40, 3408-3411
128. Moser, W. R.; Papile, C. J.; Brannon, D. A.; Duwell, R. A.; Weininger, S. J. J. Mol. Catal. 1987, 41, 271-292
129. Unruh, J. D.; Christenson, J. R. J. Mol. Catal. 1982, 14, 19-34
130. Casey, P. C.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Petrovich, L. M.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 11817-11825
131. Kamer, P. C. J.; Kranenburg, M.; van Leeuwen, P. W. N. M. Book of Abstracts, XVIth International Conference Organometallic Chemistry, University of Sussex; July 10-15, 1994; The Royal Society of Chemistry, Dalton Division, Abstract no. OC 18.
132. Kamer, P. C. J.; van Leeuwen, P. W. N. M.; de Vries, J. G. DSM N. V.; Belgium Patent 9400470, 1994; WO Patent 9530680, 1995; Chem. Abstr. 1996, 124, 186640.
133. Zuidema, E.; Goudriaan, P. E.; Swennenhuis, B. H. G.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.; Spek, A. L. Organometallics 2010, 29, 1210-1221
134. Bronger, R. P. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 2003, 22, 5358-5396
135. Bronger, R. P. J.; Bermon, J. P.; Herwig, J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Adv. Synth. Catal. 2004, 346, 789-799
136. Van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. 1999, 38, 336-338
137. Bohnen, H.; Herwig, J. Celanese Chemicals Europe GmbH; World Patent WO 02/068369, 2002; Chem. Abstr. 2002, 137, 187386.
138. Rafter, E.; Gilheany, D. G.; Reek, J. N. H.; van Leeuwen, P. W. N. M. ChemCatChem 2010, 2, 387-391
139. Klein, H.; Jackstell, R.; Beller, M. Chem. Commun. 2005, 2283-2285
140. Jackstell, R.; Klein, H.; Beller, M.; Wiese, K.-D.; Röttger, D. Eur. J. Org. Chem. 2001, 3871-3877
141. Interestingly, in early times, phosphites were considered as less valuable: Pruett, R. L. Adv. Organometal. Chem. 1979, 17, 1-60
142. Van Leeuwen, P. W. N. M.; Roobeek, C. Shell International Research Maatschappij B. V.; EP Patent 0054986, 1981; Chem. Abstr. 1982, 97, 144366.
143. Abatjoglou, A. G.; Bryant, D. R.; Maher, J. M. Union Carbide Chemicals & Plastics Technology Corporation; EP Patent 0697391, 1995; Chem. Abstr. 1996, 124, 316213.
144. Polo, A.; Claver, C.; Castillón, S.; Ruiz, A.; Bayón, J. C.; Real, J.; Mealli, C.; Masi, D. Organometallics 1992, 11, 3525-3533
145. Davies, S. G. Organotransition Metal Chemistry Application to Organic Synthesis; Pergamon Press: Oxford, UK, 1982; pp 285-287.
146. Billig, E.; Abatjoglou, A. G.; Bryant, D. R. Union Carbide Corporation; EP Patent 213639, 1987, Chem. Abstr. 1987, 107, 7392; EP Patent 214622, 1987, Chem. Abstr. 1987, 107, 25126; U.S. Patent 4769498, 1988, Chem. Abstr. 1989, 111, 117287.
147. Paciello, R.; Siggel, L.; Kneuper, H.-J.; Walker, N.; Röper, M. J. Mol. Catal. A: Chem. 1999, 143, 85-97
148. Vogl, C.; Paetzold, E.; Fischer, C.; Kragl, U. J. Mol. Catal. A: Chem. 2005, 232, 41-44
149. Behr, A.; Obst, D.; Schulte, Ch.; Schosser, T. J. Mol. Catal. A: Chem. 2003, 206, 179-184
150. Schäffner, B.; Schäffner, F.; Verevkin, S.; Börner, A. Chem. Rev. 2010, 110, 4551-4581
151. Behr, A.; Obst, D.; Turkowski, B. J. Mol. Catal. A: Chem. 2005, 226, 215-219
152. Piras, I.; Jennerjahn, R.; Jackstell, R.; Baumann, W.; Spannenberg, A.; Franke, R.; Wiese, K.-D.; Beller, M. J. Organomet. Chem. 2010, 695, 479-486
153. Börner, A.; Hess, D.; Röttger, D.; Selent, D. Oxeno Olefinchemie GmbH; European Patent EP 1099678, 2000; Chem. Abstr. 2001, 134, 352979.
154. Börner, A.; Hess, D.; Röttger, D.; Selent, D. Oxeno Olefinchemie GmbH; European Patent EP 1099677, 2000; Chem. Abstr. 2001, 134, 352978.
155. Selent, D.; Röttger, D.; Wiese, K.-D.; Börner, A. Angew. Chem., Int. Ed. 2000, 39, 1639-1641
156. Selent, D.; Baumann, W.; Kempe, R.; Spannenberg, A.; Röttger, D.; Wiese, K.-D.; Börner, A. Organometallics 2003, 22, 4265-4271
157. Jakuttis, M.; Schönweiz, A.; Werner, S.; Franke, R.; Wiese, K.-D.; Haumann, M.; Wasserscheid, P. Angew. Chem., Int. Ed. 2011, 50, 4492-4495
158. Selent, D.; Boerner, A.; Borgmann, C.; Hess, D.; Wiese, K.-D. Oxeno Olefinchemie GmbH; German Patent DE 10140086, 2003; Chem. Abstr. 2003, 138, 187924.
159. Borgmann, C.; Selent, D.; Boerner, A.; Wiese, K.-D.; Ortmann, D.; Moeller, O.; Hess, D. Oxeno Olefinchemie G.m.b.H.; WO Patent 2005090276, 2005; Chem. Abstr. 2005, 143, 346799.
160. Selent, D.; Hess, D.; Wiese, K.-D.; Röttger, D.; Kunze, C.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1696-1698
161. Selent, D.; Wiese, K.-D.; Börner, A. O -Acylphosphites: New and promising ligands for isomerising hydroformylation; In Catalysis of Organic Reactions; Sowa, Jr., J. R., Ed.; Taylor & Francis: Boca Raton, 2005, 459-469.
162. Christiansen, A.; Franke, R.; Fridag, D.; Hess, D.; Kreidler, B.; Selent, D.; Börner, A. Evonik Oxeno GmbH; WO Patent 2013/068232, 2012; Chem. Abstr. 2013, 158, 728315.
163. Yan, Y.; Zhang, X.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 16058-16061
164. Yu, S.; Chie, Y.-m.; Guan, Z.-h.; Zhang, X. Org. Lett. 2008, 10, 3469-3472
165. Burke, P. M.; Garner, J. M.; Tam, W.; Kreutzer, K. A.; Teunissen, A. J. J. DSM N. V./Du Pont de Nemours and Company; WO Patent 97/33854, 1997; Chem. Abstr. 1997, 127, 294939.
166. Cobley, C. J.; Hanson, C. H.; Loyd, M. C.; Simmonds, S. Org. Process Res. Dev. 2011, 15, 284-290
167. Muilwijk, K. F.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Am. Oil Chem. Soc. 1997, 74, 223-228
168. Yuki, Y.; Takahashi, K.; Tanaka, Y.; Nozaki, K. J. Am. Chem. Soc. 2013, 135, 17393-17400
169. Beller, M.; Zimmermann, B.; Geissler, H. Chem. - Eur. J. 1999, 5, 1301-1305
170. Evans, D.; Osborn, J. A.; Jardine, F. H.; Wilkinson, G. Nature 1965, 208, 1203-1204
171. Teleshev, A. T.; Kolesnichenko, N. V.; Markova, N. A.; Slivinskii, E. V.; Kurkin, V. I.; Demina, E. M.; Korneeva, G. A.; Loktev, C. M.; Nifant'ev, E. E. Neftekhimiya 1991, 31, 11-16
172. Ojima, I.; Kato, K.; Okabe, M.; Fuchikami, T. J. Am. Chem. Soc. 1987, 109, 7714-7720
173. Schulz, H. F.; Bellstedt, F. Ind. Eng. Chem. Prod. Res. Dev. 1973, 12, 176-183
174. McGrath, D. V.; Grubbs, R. H. Organometallics 1994, 13, 224-235
175. Karlen, T.; Ludi, A. Helv. Chim. Acta 1992, 75, 1604-1606
176. Wang, D.; Chen, D.; Haberman, J. X.; Li, C.-J. Tetrahedron 1998, 54, 5129-5142
177. Knifton, J. F. J. Mol. Catal. 1988, 47, 99-116
178. Dharmasena, U. L.; Foucault, H. M.; dos Santos, E. N.; Fogg, D. E.; Nolan, S. P. Organometallics 2005, 24, 1056-1058
179. Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair, R.; Sharma, A. J. Am. Chem. Soc. 2007, 129, 9592-9593
180. Jenck, J.; Kalck, P.; Pinelli, E.; Siani, M.; Thorez, A. J. Chem. Soc., Chem. Commun. 1988, 1428-1430
181. Kalck, P.; Siani, M.; Jenck, J.; Peyrille, B.; Peres, Y. J. Mol. Catal. 1991, 67, 19-27
182. Knifton, J. F. J. Mol. Catal. 1987, 43, 65-77
183. Fleischer, I.; Dyballa, K. M.; Jennerjahn, R.; Jackstell, R.; Franke, R.; Spannenberg, A.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 2949-2953
184. Fleischer, I.; Wu, L.; Profir, I.; Jackstell, R.; Franke, R.; Beller, M. Chem. - Eur. J. 2013, 19, 10589-10594
185. Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506
186. Bedekovits, A.; Kollár, L.; Kégl, T. Inorg. Chim. Acta 2010, 363, 2029-2045
187. Da Silva, J. C. S.; Dias, R. P.; de Almeida, W. B.; Rocha, W. R. J. Comput. Chem. 2010, 10.1002/jcc.21483
188. Clark, H. C.; Kurosawa, H. J. Chem. Soc., Chem. Commun. 1972, 150-151
189. Inorg. Chem. 1972, 11, 1275-1280.
190. Inorg. Chem. 1973, 12, 357-362.
191. Inorg. Chem. 1973, 12, 1566-1569.
192. Cavinato, G.; De Munno, G.; Lami, M.; Marchionna, M.; Toniolo, L.; Viterbo, D. J. Organomet. Chem. 1994, 466, 277-282
193. Van Leeuwen, P. W. N. M.; Roobeek, C. F.; Wife, R. L.; Frijns, J. H. G. J. Chem. Soc., Chem. Commun. 1986, 31-33
194. van Leeuwen, P. W. N. M.; Roobeek, C. F. New J. Chem. 1990, 14, 487-493
195. Cavinato, G.; De Munno, G.; Lami, M.; Marchionna, M.; Toniolo, L.; Viterbo, D. J. Organomet. Chem. 1994, 466, 277-282
196. Tang, S. C.; Kim, L. J. Mol. Catal. 1982, 14, 231-240
197. Kim, L.; Tang, S. C. Shell Oil Company; U.S. Patent 4,198,352, 1980; Chem. Abstr. 1980, 93, 149795.
198. Kawabata, Y.; Hayashi, T.; Ogata, I. J. Chem. Soc., Chem. Comm. 1979, 462-463
199. Clark, H. C.; Davies, J. A. J. Organomet. Chem. 1981, 213, 503-512
200. Van der Veen, L. A.; Keeven, P. K.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Commun. 2000, 333-334
201. Van der Veen, L.; Keeven, P. K.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 2000, 2105-2112
202. Van Duren, R.; van der Vlugt, J. I.; Kooijman, H.; Spek, A. L.; Vogt, D. Dalton Trans. 2007, 1053-1059
203. Meessen, P.; Vogt, D.; Keim, W. J. Organomet. Chem. 1998, 551, 165-170
204. Wasserscheid, P.; Waffenschmidt, H. J. Mol. Catal. A: Chem. 2000, 164, 61-67
205. Burke, P. M.; Gelling, O. J.; Oevering, H.; Toth, I. E.I. Du Pont de Nemours and Company; WO Patent 97/08127, 1997; Chem. Abstr. 1997, 126, 225032.
206. Gelling, O. J.; Toth, I. DSM N. Y.; E.I. Du Pont de Nemours and Company; WO Patent 95/18783, 1995; Chem. Abstr. 1995, 123, 285242.
207. Gottardo, M.; Scarso, A.; Paganelli, S.; Strukul, G. Adv. Synth. Catal. 2010, 352, 2251-2262
208. Fang, X.; Zhang, M.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 4645-4649
209. Kiss, G. Chem. Rev. 2001, 101, 3435-3456
210. Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663-681
211. Gauthier, D.; Lindhardt, A. T.; Olsen, E. P. K.; Overgaard, J.; Skrydstrup, T. J. Am. Chem. Soc. 2010, 132, 7998-8009
212. Drent, E.; Budzelaar, P. H. M. J. Organomet. Chem. 2000, 593-594, 211-225
213. Drent, E.; Pello, D. H.; Suykerbuyk, J. C. L. J.; van Gogh, J. Shell Internationale Research Maatschappij B. V.; WO Patent 95/05354, 1995; Chem. Abstr. 1995, 123, 313386.
214. Drent, E.; Jager, W. W. Shell Oil Company; U.S. Patent 5,780,684, 1998; Chem. Abstr. 1998, 129, 137605.
215. Arnoldy, P.; Bolinger, C. M.; Mul, W. P. Shell Internationale Research Maatschappij B. V.; EP Patent 0900776, 1998; Chem. Abstr. 1999, 130, 224604.
216. Arnoldy, P.; Bolinger, C. M.; Drent, E.; Keijsper, J. J. Shell Internationale Research Maatschappij B. V.; EP Patent 0903333, 1999; Chem. Abstr. 1999, 130, 268829.
217. Konya, D.; Almeida Leñero, K. Q.; Drent, E. Organometallics 2006, 25, 3166-3174
218. The insertion of CO in the Pd-C bond to form an acylpalladium species can be supported by cobalt cocatalysts: Fukuoka, A.; Fukagawa, S.; Hitano, M.; Komiya, S. Chem. Lett. 1997, 377-378
219. Jennerjahn, R.; Piras, I.; Jackstell, R.; Franke, R.; Wiese, K.-D.; Beller, M. Chem. - Eur. J. 2009, 15, 6383-6388
220. Van der Drift, E. C.; Bouwman, E.; Drent, E. J. Organomet. Chem. 2002, 650, 1-24
221. Long, G. T.; Weitz, E. J. Am. Chem. Soc. 2000, 122, 1431-1442
222. Frankel, E.; Emken, E.; Davison, V. J. Am. Oil Chem. Soc. 1966, 43, 307-311
223. Graff, J. L.; Sanner, R. D.; Wrighton, M. S. Organometallics 1982, 1, 837-842
224. Jennerjahn, R.; Jackstell, R.; Piras, I.; Franke, R.; Jiao, H.; Bauer, M.; Beller, M. ChemSusChem 2012, 5, 734-739
225. Booth, B. L.; Goldwhite, H.; Haszeldine, R. N. J. Chem. Soc. C 1966, 1447-1449
226. Kang, H.; Mauldin, C. H.; Cole, T.; Slegir, W.; Pettit, R. J. Am. Chem. Soc. 1977, 99, 8323-8325
227. Evans, D.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1968, 3133-3142
228. Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli, G. J. Organomet. Chem. 2000, 607, 57-63
229. Trzeciak, A. M.; Mieczyńska, E.; Ziółkowski, J. J. Top. Catal. 2000, 11/12, 461-468
230. Beigi, M.; Ricken, S.; Müller, K. S.; Koç, F.; Eilbracht, P. Eur. J. Org. Chem. 2011, 1482-1492 and references cited therein
231. Crozet, D.; Urrutigoïty, M.; Kalck, P. ChemCatChem 2011, 3, 1102-1118
232. Seayad, A.; Ahmed, M.; Klein, H.; Jackstell, R.; Gross, T.; Beller, M. Science 2002, 297, 1676-1678
233. Ahmed, M.; Bronger, R. P. J.; Jackstell, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Beller, M. Chem. - Eur. J. 2006, 12, 8979-8988
234. Liu, G.; Huang, K.; Cao, B.; Chang, M.; Li, S.; Yu, S.; Zhou, L.; Wu, W.; Zhang, X. Org. Lett. 2012, 14, 102-105
235. Wu, L.; Fleischer, I.; Jackstell, R.; Beller, M. J. Am. Chem. Soc. 2013, 135, 3989-3996
236. Until now, yields and n/iso selectivities in the hydroformylation of 2-olefins have been very low: Piras, I.; Jennerjahn, R.; Jackstell, R.; Spannenberg, A.; Franke, R.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 280-284
237. Recently, a one-pot palladium-catalyzed isomerization/rhodium-catalyzed hydroformylation sequence of ω-unsaturated carboxylic acids was reported that selectively afforded α-methyl branched aldehydes: Dydio, P.; Ploeger, M.; Reek, J. N. ACS Catal. 2013, 3, 2939-2942