Combining Experimental and Computational Studies to Understand and Predict Reactivities of Relevance to Homogeneous Catalysis

Chemistry - A European Journal

Volumn 20, Issue 50, 2014, Pages 16432-16441

  Tsang, Althea S K ^a   Sanhueza, Italo A ^a,b   Schoenebeck, Franziska ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

computational chemistry; design; homogeneous catalysis; reaction mechanisms; synthesis

Indexed keywords

CATALYSIS; DESIGN; SYNTHESIS (CHEMICAL);

CASE-STUDIES; COMPUTATIONAL STUDIES; COMPUTATIONAL TOOLS; HOMOGENEOUS CATALYSIS; REACTION MECHANISM; REACTIVITY STUDIES;

COMPUTATIONAL CHEMISTRY;

EID: 84939569473     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404725     Document Type: Article

References (121)

1. Selected books, see:
2. C. J. Cramer, Essentials of Computational Chemistry: Theories and Models, Wiley, Chichester, 2004;
3. F. Jensen, Introduction to Computational Chemistry, Wiley, Chichester, 1999;
4. G. H. Grant, W. G. Richards, Computational Chemistry, Oxford University Press, Oxford 1995;
5. D. Young, Computational Chemistry: A Practical Guide for Applying Techniques to Real World Problems, Wiley, New York, 2001;
6. P. G. Andersson, E. Clot, P.-O. Norrby, Modeling in Homogeneous Catalysis: A Tutorial, Wiley-VCH, Weinheim 2012;
7. F. Maseras, A. Lledõs, in Computational Methods for Homogeneous Catalysis, Vol25, Springer, Heidelberg, 2002.
8. For selected examples:
9. W. Thiel, Angew. Chem. Int. Ed. 2011, 50, 9216;
10. Angew. Chem. 2011, 123, 9382;
11. Z. Lin, Acc. Chem. Res. 2010, 43, 602;
12. W. Thiel, G. Hummer, Nature 2013, 504, 96;
13. K. N. Houk, P. H.-Y. Cheong, Nature 2008, 455, 309;
14. D. Balcells, E. Clot, O. Eisenstein, Chem. Rev. 2010, 110, 749;
15. Q. N. N. Nguyen, D. J. Tantillo, Chem. Asian J. 2014, 9, 674;
16. L. Noodleman, T. Lovell, W.-G. Han, J. Li, F. Himo, Chem. Rev. 2004, 104, 459.
17. The Nobel Prize in Chemistry 2013, http://www.nobelprize.org/nobel-prizes/chemistry/laureates/2013/;
18. The Nobel Prize in Chemistry 1998, http://www.nobelprize.org/nobel-prizes/chemistry/laureates/1998/.
19. R. Lonsdale, J. N. Harvey, A. J. Mulholland, Chem. Soc. Rev. 2012, 41, 3025.
20. A. C. T. vanDuin, S. Dasgupta, F. Lorant, W. A. Goddard, J. Phys. Chem. A 2001, 105, 9396;
21. K. D. Nielson, A. C. T. vanDuin, J. Oxgaard, W.-Q. Deng, W. A. Goddard III, J. Phys. Chem. A 2005, 109, 493;
22. S. Grimme, J. Chem. Theory Comput. 2014, 10, 4497;
23. W. Thiel, in Theory and Applications of Computational Chemistry: The First Forty Years (Eds.:, C. Dykstra, G. Frenking, K. Kim, G. Scuseria,), Chapter 21, p. 559;
24. C. Doubleday, C. P. Suhrada, K. N. Houk, J. Am. Chem. Soc. 2006, 128, 90.
25. Q. Wu, W. Yang, J. Chem. Phys. 2002, 116, 515;
26. S. Grimme, J. Comput. Chem. 2004, 25, 1463;
27. C. Morgado, M. A. Vincent, I. H. Hillier, X. Shan, Phys. Chem. Chem. Phys. 2007, 9, 448;
28. P. Jurecka, J. Cerny, P. Hobza, D. R. Salahub, J. Comput. Chem. 2007, 28, 555;
29. Y. Zhao, D. G. Truhlar, J. Phys. Chem. A 2005, 109, 5656.
30. For examples:
31. H. Jacobsen, L. Cavallo, ChemPhysChem 2012, 13, 562;
32. P. Rönnholm, S. O. NilssonLill, J. Grafenstein, P.-O. Norrby, M. Pettersson, G. Hilmersson, ChemPlusChem 2012, 77, 799.
33. J. Mahatthananchai, A. M. Dumas, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 10954;
34. Angew. Chem. 2012, 124, 11114;
35. F. Proutiere, F. Schoenebeck, Angew. Chem. Int. Ed. 2011, 50, 8192;
36. Angew. Chem. 2011, 123, 8342;
37. F. Proutiere, F. Schoenebeck, Synlett 2012, 23, 645.
38. Representative examples:
39. M. Aufiero, F. Proutiere, F. Schoenebeck, Angew. Chem. Int. Ed. 2012, 51, 7226;
40. Angew. Chem. 2012, 124, 7338;
41. D. C. Powers, E. Lee, A. Ariafard, M. S. Sanford, B. F. Yates, A. J. Canty, T. Ritter, J. Am. Chem. Soc. 2012, 134, 12002;
42. J. N. Harvey, Nat. Chem. 2013, 5, 643;
43. H. Schwarz, Angew. Chem. Int. Ed. 2011, 50, 10096;
44. Angew. Chem. 2011, 123, 10276.
45. For examples, see:
46. C. P. Butts, E. Filali, G. C. Lloyd-Jones, P.-O. Norrby, D. A. Sale, Y. Schramm, J. Am. Chem. Soc. 2009, 131, 9945;
47. M. Besora, A. C. Braga, G. Ujaque, F. Maseras, A. Lledõs, Theor. Chem. Acc. 2011, 128, 639.
48. D. Balcells, F. Maseras, New J. Chem. 2007, 31, 333;
49. H.-Y. Cheong, C. Y. Legault, J. M. Um, N. Celebi-Olcum, K. N. Houk, Chem. Rev. 2011, 111, 5042.
50. P. J. Donoghue, P. Helquist, P.-O. Norrby, O. Wiest, J. Chem. Theory Comput. 2008, 4, 1313;
51. P. J. Donoghue, P. Helquist, P.-O. Norrby, O. Wiest, J. Am. Chem. Soc. 2009, 131, 410.
52. J. M. Brown, R. J. Deeth, Angew. Chem. Int. Ed. 2009, 48, 4476;
53. Angew. Chem. 2009, 121, 4544;
54. A. Armstrong, R. A. Boto, P. Dingwall, J. Contreras-Garcia, M. J. Harvey, N. J. Mason, H. S. Rzepa, Chem. Sci. 2014, 5, 2057.
55. L. Xu, M. J. Hilton, X. Zhang, P.-O. Norrby, Y.-D. Wu, M. S. Sigman, O. Wiest, J. Am. Chem. Soc. 2014, 136, 1960.
56. J. Llaveria, A. Beltrán, W. M. C. Sameera, A. Locati, M. M. Díaz-Requejo, M. I. Matheu, S. Castillõn, F. Maseras, P. J. Pérez, J. Am. Chem. Soc. 2014, 136, 5342.
57. H. Teller, M. Corbet, L. Mantilli, G. Gopakumar, R. Goddard, W. Thiel, A. Fürstner, J. Am. Chem. Soc. 2012, 134, 15331.
58. M. R. Luzung, P. Mauleõn, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 12402.
59. E. Lyngvi, J. W. Bode, F. Schoenebeck, Chem. Sci. 2012, 3, 2346.
60. J. Kaeobamrung, J. Mahatthananchai, P. Zheng, J. W. Bode, J. Am. Chem. Soc. 2010, 132, 8810;
61. J. Mahatthananchai, J. W. Bode, Chem. Sci. 2012, 3, 192.
62. For similar observations, see:, R. C. Samanta, B. Maji, S. DeSarkar, K. Bergander, R. Fröhlich, C. Mück-Lichtenfeld, H. Mayr, A. Studer, Angew. Chem. Int. Ed. 2012, 51, 5234;
63. Angew. Chem. 2012, 124, 5325.
64. For a related example, see:, S. E. Allen, J. Mahatthananchai, J. W. Bode, M. C. Kozlowski, J. Am. Chem. Soc. 2012, 134, 12098.
65. Selected examples:
66. Y. Schmidt, J. K. Lam, H. V. Pham, K. N. Houk, C. D. Vanderwal, J. Am. Chem. Soc. 2013, 135, 7339;
67. S. T. Henriksen, P. Norrby, P. Kaukiranta, P. G. Andersson, J. Am. Chem. Soc. 2008, 130, 10414;
68. K. J. Bonney, F. Schoenebeck, Chem. Soc. Rev. 2014, 43, 6609;
69. I. A. Sanhueza, A. M. Wagner, M. S. Sanford, F. Schoenebeck, Chem. Sci. 2013, 4, 2767;
70. F. Proutiere, M. Aufiero, F. Schoenebeck, J. Am. Chem. Soc. 2012, 134, 606;
71. S. Zhou, G. M. Anderson, B. Mondal, E. Doni, V. Ironmonger, M. Kranz, T. Tuttle, J. A. Murphy, Chem. Sci. 2014, 5, 476;
72. S. Diethelm, F. Schoenebeck, E. M. Carreira, Org. Lett. 2014, 16, 960;
73. D. S. B. Daniels, A. S. Jones, A. L. Thompson, R. S. Paton, E. A. Anderson, Angew. Chem. Int. Ed. 2014, 53, 1915;
74. Angew. Chem. 2014, 126, 1946.
75. P. R. Schreiner, H. P. Reisenauer, D. Ley, D. Gerbig, C.-H. Wu, W. D. Allen, Science 2011, 332, 1300.
76. M. N. Grayson, J. M. Goodman, J. Am. Chem. Soc. 2013, 135, 6142.
77. M. C. Nielsen, E. Lyngvi, F. Schoenebeck, J. Am. Chem. Soc. 2013, 135, 1978.
78. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094;
79. Angew. Chem. 2009, 121, 5196;
80. K. Muñiz, Angew. Chem. Int. Ed. 2009, 48, 9412;
81. Angew. Chem. 2009, 121, 9576;
82. A. J. Hickman, M. S. Sanford, Nature 2012, 484, 177.
83. K. J. Bonney, F. Proutiere, F. Schoenebeck, Chem. Sci. 2013, 4, 4434;
84. C. T. Hunt, A. L. Balch, Inorg. Chem. 1982, 21, 1641.
85. D. C. Powers, D. Benitez, E. Tkatchouk, W. A. Goddard III, T. Ritter, J. Am. Chem. Soc. 2010, 132, 14092.
86. Selected examples:
87. J. B. Siegel, A. Zanghellini, H. M. Lovick, G. Kiss, A. R. Lambert, J. L. Gallaher, D. Hilvert, M. H. Gelb, B. L. Stoddard, K. N. Houk, F. E. Michael, D. Baker, Science 2010, 329, 309;
88. M. C. Kozlowski, S. L. Dixon, M. Panda, G. Lauri, J. Am. Chem. Soc. 2003, 125, 6614;
89. J. C. Ianni, V. Annamalai, P.-W. Phuan, M. C. Kozlowski, Angew. Chem. Int. Ed. 2006, 45, 5502;
90. Angew. Chem. 2006, 118, 5628;
91. P. J. Donoghue, P. Helquist, P. O. Norrby, O. Wiest, J. Am. Chem. Soc. 2009, 131, 410;
92. D. J. Tantillo, Angew. Chem. Int. Ed. 2009, 48, 31;
93. Angew. Chem. 2009, 121, 33.
94. For recent reviews, see:
95. G. Bifulco, P. Dambruoso, L. Gomez-Paloma, R. Riccio, Chem. Rev. 2007, 107, 3744;
96. S. DiMicco, M. G. Chini, R. Riccio, G. Bifulco, Eur. J. Org. Chem. 2010, 1411;
97. M. W. Lodewyk, M. R. Siebert, D. J. Tantillo, Chem. Rev. 2012, 112, 1839. Selected examples of Si, P-shift predictions:
98. C. Zhang, P. Patschinski, D. S. Stephenson, R. Panisch, J. H. Wender, M. C. Holthausen, H. Zipse, Phys. Chem. Chem. Phys. 2014, 16, 16642.
99. M. W. Lodewyk, C. Soldi, P. B. Jones, M. M. Olmstead, J. Rita, J. T. Shaw, D. J. Tantillo, J. Am. Chem. Soc. 2012, 134, 18550;
100. M. W. Lodewyk, D. J. Tantillo, J. Nat. Prod. 2011, 74, 1339;
101. B. D. Schwartz, L. V. White, M. G. Banwell, A. C. Willis, J. Org. Chem. 2011, 76, 8560.
102. D. J. Shepherd, P. A. Broadwith, B. S. Dyson, R. S. Paton, J. W. Burton, Chem. Eur. J. 2013, 19, 12644.
103. K. Rudolf, D. C. Spellmeyer, K. N. Houk, J. Org. Chem. 1987, 52, 3708.
104. Examples and reviews:
105. A. McNally, C. K. Prier, D. W. C. MacMillan, Science 2011, 334, 1114;
106. M. W. Kanan, M. M. Rozenman, K. Sakurai, T. M. Snyder, D. R. Liu, Nature 2004, 431, 545;
107. A. B. Beeler, S. Su, C. A. Singleton, J. A. Porco Jr., J. Am. Chem. Soc. 2007, 129, 1413;
108. Y. Chen, A. S. Kamlet, J. B. Steinman, D. R. Liu, Nat. Chem. 2011, 3, 146;
109. J. W. Szewczyk, R. L. Zuckerman, R. G. Bergman, J. A. Ellman, Angew. Chem. Int. Ed. 2001, 40, 216;
110. Angew. Chem. 2001, 113, 222;
111. D. W. Robbins, J. F. Hartwig, Science 2011, 333, 1423;
112. P. Cong, R. D. Doolen, Q. Fan, D. M. Giaquinta, S. Guan, E. W. McFarland, D. M. Poojary, K. Self, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 483;
113. Angew. Chem. 1999, 111, 507;
114. M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stöckigt, Angew. Chem. Int. Ed. 1999, 38, 1758;
115. Angew. Chem. 1999, 111, 1872.
116. M. Kheirabadi, N. Çelebi-Ölçüm, M. F. L. Parker, Q. Zhao, G. Kiss, K. N. Houk, C. E. Schafmeister, J. Am. Chem. Soc. 2012, 134, 18345.
117. P. Anstaett, F. Schoenebeck, Chem. Eur. J. 2011, 17, 12340.
118. M. C. Nielsen, K. J. Bonney, F. Schoenebeck, Angew. Chem. Int. Ed. 2014, 53, 5903;
119. Angew. Chem. 2014, 126, 6013.
120. In addition to Xantphos, also two biaryl ligands (RuPhos and BrettPhos) were capable of triggering reductive elimination, see:, E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679.
121. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 4632.