Nickel-catalyzed decarboxylative C-P cross-coupling of alkenyl acids with P(O)H compounds

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 8118-8127

  Wu, Yile ^a   Liu, Liu Leo ^a   Yan, Kaili ^a   Xu, Pengxiang ^a   Gao, Yuxing ^a   Zhao, Yufen ^a,b  

^a XIAMEN UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; NICKEL; PHOSPHORUS COMPOUNDS;

CATALYTIC PERFORMANCE; CROSS-COUPLINGS; DFT CALCULATION; HIGH STEREOSELECTIVITIES; NITROGEN LIGAND; NUCLEOPHILICITIES; PHOSPHINE LIGANDS; REDUCTIVE ELIMINATION;

LIGANDS;

1 ALKENYLPHOSPHINATE OXIDE; 1 ALKENYLPHOSPHINE OXIDE; 1 ALKENYLPHOSPHONATE; ALKENYL GROUP; CARBON; HYDROXIDE; LIGAND; NICKEL; NITROGEN; PHOSPHINE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG; ALKENE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DECARBOXYLATION; DENSITY FUNCTIONAL THEORY; ELIMINATION REACTION; NUCLEOPHILICITY; REDUCTION; STEREOCHEMISTRY; CHEMISTRY; QUANTUM THEORY; STEREOISOMERISM;

ALKENES; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; NICKEL; NITROGEN; ORGANOPHOSPHONATES; PHOSPHINES; QUANTUM THEORY; STEREOISOMERISM;

EID: 84910014596     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501321m     Document Type: Article

References (98)

1. McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151
2. Van der Jeught, S.; Stevens, C. V. Chem. Rev. 2009, 109, 2672
3. Kollár, L.; Keglevich, G. Chem. Rev. 2010, 110, 4257
4. Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981
5. Lassaux, P.; Hamel, M.; Gulea, M.; Delbruck, H.; Mercuri, P. S.; Horsfall, L.; Dehareng, D.; Kupper, M.; Frere, J.-M.; Hoffmann, K.; Galleni, M.; Bebrone, C. J. Med. Chem. 2010, 53, 4862
6. Chou, H. H.; Cheng, C. H. Adv. Mater. 2010, 22, 2468
7. Bae, Y. U.; Yoon, T. H. J. Appl. Polym. Sci. 2012, 123, 3298
8. Monge, S.; Canniccioni, B.; Graillot, A.; Robin, J.-J. Biomacromolecules 2011, 12, 1973
9. Delomenède, M.; Bedos-Belval, F.; Duran, H.; Vindis, C.; Baltas, M.; Nègre-Salvayre, A. J. Med. Chem. 2008, 51, 3171
10. Bhattacharya, A. K.; Rana, K. C. Bioorg. Med. Chem. 2011, 19, 7129
11. Tonelli, F.; Lim, K. G.; Loveridge, C.; Long, J.; Pitson, S. M.; Tigyi, G.; Bittman, R.; Pyne, S.; Pyne, N. J. Cell. Signalling 2010, 22, 1536
12. Price, D.; Pyrah, K.; Hull, T. R.; Milnes, G. J.; Ebdon, J. R.; Hunt, B. J.; Joseph, P. Polym. Degrad. Stab. 2002, 77, 227
13. Yamada, M.; Honma, I. Polymer 2005, 46, 2986
14. Ajellal, N.; Thomas, C. M.; Carpentier, J.-F. Polymer 2008, 49, 4344
15. Macarie, L.; Ilia, G. Prog. Polym. Sci. 2010, 35, 1078 and references cited therein
16. Duan, Z.-C.; Hu, X.-P.; Wang, D.-Y.; Huang, J.-D.; Yu, S.-B.; Deng, J.; Zheng, Z. Adv. Synth. Catal. 2008, 350, 1979
17. Cullen, S. C.; Rovis, T. Org. Lett. 2008, 10, 3141
18. Cheruku, P.; Paptchikhine, A.; Church, T. L.; Andersson, P. G. J. Am. Chem. Soc. 2009, 131, 8285
19. Konno, T.; Shimizu, K.; Ogata, K.; Fukuzawa, S. J. Org. Chem. 2012, 77, 3318
20. Coote, S. C.; Bach, T. J. Am. Chem. Soc. 2013, 135, 14948
21. Al-Maksoud, W.; Mesnager, J.; Jaber, F.; Pinel, C.; Djakovitch, L. J. Organomet. Chem. 2009, 694, 3222
22. Burini, A.; Cacchi, S.; Pace, P.; Pietroni, B. R. Synlett 1995, 677
23. Kabalka, G. W.; Guchhait, S. K.; Naravane, A. Tetrahedron Lett. 2004, 45, 4685
24. Chatterjee, A. K.; Choi, T.-L.; Grubbs, R. H. Synlett 2001, 1034
25. Bisaro, F.; Gouverneur, V. Tetrahedron Lett. 2003, 44, 7133
26. Vinokurov, N.; Michrowska, A.; Szmigielska, A.; Drzazga, Z.; Wójciuk, G.; Demchuk, O. M.; Grela, K.; Pietrusiewicz, K. M.; Butenschön, H. Adv. Synth. Catal. 2006, 348, 931
27. Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681
28. Evano, G.; Tadiparthi, K.; Couty, F. Chem. Commun. 2011, 47, 179
29. Jouvin, K.; Coste, A.; Bayle, A.; Legrand, F.; Karthikeyan, G.; Tadiparthi, K.; Evano, G. Organometallics 2012, 31, 7933
30. Liu, L.; Wang, Y.; Zeng, Z.; Xu, P.; Gao, Y.; Yin, Y.; Zhao, Y. Adv. Synth. Catal. 2013, 355, 659
31. Han, L.-B.; Zhao, C.-Q.; Onozawa, S.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842
32. Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080
33. Niu, M.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Commun. 2007, 272
34. Nune, S. K.; Tanaka, M. Chem. Commun. 2007, 2858
35. Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P.; Starikova, Z. A. Adv. Synth. Catal. 2010, 352, 2979
36. Evano, G.; Gaumont, A.-C.; Alayrac, C.; Wrona, I. E.; Giguere, J. R.; Delacroix, O.; Bayle, A.; Jouvin, K.; Theunissen, C.; Gatignol, J.; Silvanus, A. C. Tetrahedron 2014, 70, 1529
37. Gooßen, L. J.; Gooßen, K. Top. Organomet. Chem. 2013, 44, 121
38. Rokade, B. V.; Prabhu, K. R. Org. Biomol. Chem. 2013, 11, 6713
39. Duan, Z.; Ranjit, S.; Zhang, P.; Liu, X. Chem.-Eur. J. 2009, 15, 3666
40. Hu, J.; Zhao, N.; Yang, B.; Wang, G.; Guo, L.-N.; Liang, Y.-M.; Yang, S.-D. Chem.-Eur. J. 2011, 17, 5516
41. Li, X.; Yang, F.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 992
42. Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738
43. Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem., Int. Ed. 2009, 48, 792
44. Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006
45. Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030
46. Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653
47. Miao, J.; Ge, H. Org. Lett. 2013, 15, 2930
48. Yoshino, Y.; Kurahashi, Y.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 7494
49. Choe, J.; Yang, J.; Park, K.; Palani, T.; Lee, S. Tetrahedron Lett. 2012, 53, 6908
50. Yang, K.; Zhang, C.; Wang, P.; Zhang, Y.; Ge, H. Chem.-Eur. J. 2014, 20, 7241
51. Goossen, L. J.; Lange, P. P.; Rodriguez, N.; Linder, C. Chem.-Eur. J. 2010, 16, 3906
52. Zhang, S.-L.; Fu, Y.; Shang, R.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638
53. Shen, Z.; Ni, Z.; Mo, S.; Wang, J.; Zhu, Y. Chem.-Eur. J. 2012, 18, 4859
54. Reddy, P. V.; Srinivas, P.; Annapurna, M.; Bhargava, S.; Wagler, J.; Mirzadeh, N.; Kantam, M. L. Adv. Synth. Catal. 2013, 355, 705
55. Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323
56. Xie, H.; Lin, F.; Lei, Q.; Fang, W. Organometallics 2013, 32, 6957
57. Liu, L.; Zhang, S.; Chen, H.; Lv, Y.; Zhu, J.; Zhao, Y. Chem.-Asian J. 2013, 8, 2592
58. Hu, G.; Chen, W.; Fu, T.; Peng, Z.; Qiao, H.; Gao, Y.; Zhao, Y. Org. Lett. 2013, 15, 5362
59. Wang, T.; Sang, S.; Liu, L.; Qiao, H.; Gao, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 608
60. Liu, L.; Wu, Y.; Wang, Z.; Zhu, J.; Zhao, Y. J. Org. Chem. 2014, 79, 6816
61. Cornella, J.; Lu, P.; Larrosa, I. Org. Lett. 2009, 11, 5506
62. Cornella, J.; Rosillo-Lopez, M.; Larrosa, I. Adv. Synth. Catal. 2011, 353, 1359
63. Bhadra, S.; Dzik, W. I.; Goossen, L. J. J. Am. Chem. Soc. 2012, 134, 9938
64. Sharif, H. A.; Vikse, K. L.; Khairallah, G. N.; O'Hair, R. A. J. Organometallics 2013, 32, 5416
65. Yao, J.; Feng, R.; Wu, Z.; Liu, Z.; Zhang, Y. Adv. Synth. Catal. 2013, 355, 1517
66. Daasch, L. W. J. Am. Chem. Soc. 1958, 80, 5301
67. Chen, F.; Wasylishen, R. E. Magn. Reson. Chem. 2010, 48, 270
68. Kalek, M.; Stawinski, J. Organometallics 2008, 27, 5876
69. Kohler, M. C.; Grimes, T. V.; Wang, X.; Cundari, T. R.; Stockland, R. A., Jr. Organometallics 2009, 28, 1193
70. Zhang, L.; Fang, D.-C. J. Org. Chem. 2013, 78, 2405
71. Liu, L.; Yuan, H.; Fu, T.; Wang, T.; Gao, X.; Zeng, Z.; Zhu, J.; Zhao, Y. J. Org. Chem. 2014, 79, 80
72. Liu, L.; Wu, Y.; Wang, T.; Gao, X.; Zhu, J.; Zhao, Y. J. Org. Chem. 2014, 79, 5074
73. Zuidema, E.; van Leeuwen, P. W. N. M.; Bo, C. Organometallics 2005, 24, 3703
74. Koizumi, T.; Yamazaki, A.; Yamamoto, T. Dalton Trans. 2008, 3949
75. Ariafard, A.; Yates, B. F. J. Organomet. Chem. 2009, 694, 2075
76. Lavallo, V.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Angew. Chem., Int. Ed. 2006, 45, 3488
77. Tukov, A. A.; Normand, A. T.; Nechaev, M. S. Dalton Trans. 2009, 7015
78. The highest occupied molecular orbitals (HOMO) of free dppf and bpy are mainly contributed by lone pairs on phosphorus and nitrogen atoms, respectively. The energy of HOMO (-0.20 eV) for dppf is much higher than that for bpy (-0.25 eV).
79. Gaussian 03, Revision E.01: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Wallingford, CT, 2004.
80. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
81. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623
82. Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680
83. Li, Z.; Zhang, S.-L.; Fu, Y.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 8815
84. Liu, P.; Montgomery, J.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 6956
85. Guan, W.; Sakaki, S.; Kurahashi, T.; Matsubara, S. Organometallics 2013, 32, 7564
86. Yang, G.; Schäffner, B.; Blug, M.; Hensen, E. J. M.; Pidko, E. A. ChemCatChem 2014, 6, 800
87. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28.
88. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
89. Ehlers, A.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
90. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237
91. Bondi, A. J. Phys. Chem. 1964, 68, 441
92. Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866
93. Igel-Mann, G.; Stoll, H.; Preuss, H. Mol. Phys. 1988, 65, 1321
94. Andrae, D.; Haeussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chem. Acc. 1990, 77, 123
95. Krishan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
96. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
97. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. V. R. J. Comput. Chem. 1983, 4, 294
98. Legault, C. Y. CYLview, 1.0b; Université de Sherbrooke: Sherbrooke, 2009; www.cylview.org.