Rhodium(I) mediated arylation of aldehydes with arylboronic acids under base and water free conditions: A computational study

Journal of Molecular Catalysis A: Chemical

Volumn 324, Issue 1-2, 2010, Pages 24-30

  Suarez, Alma Itzel Olivos ^a   Reek, Joost N H ^a   De Bruin, Bas ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Aldehyde; Arylation; Arylboronic acid; DFT; Rhodium

Indexed keywords

ALCOHOLATE; ARYLATIONS; ARYLBORONIC ACID; ARYLBORONIC ACIDS; BORON ATOM; COMPUTATIONAL STUDIES; DFT; DFT CALCULATION; RATE LIMITING;

ALDEHYDES; AROMATIC COMPOUNDS; BORON; BORON COMPOUNDS; CHEMICAL REACTIONS; RHODIUM;

ACIDS;

EID: 77954175848     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2010.03.002     Document Type: Article

References (49)

1. A. Susuki Pure Appl. Chem. 66 1994 213
2. N. Miyaura, and A. Susuki Chem. Rev. 95 1995 2457
3. A.A.C. Braga, N.H. Morgon, G. Ujaque, A. Lledós, and F. Maseras J. Organomet. Chem. 691 2006 4459 4466
4. A.A.C. Braga, G. Ujaque, and F. Maseras Organometallics 25 2006 3647 3658
5. A.A.C. Braga, N.H. Morgon, G. Ujaque, A. Lledós, and F. Maseras J. Am. Chem. Soc. 127 2005 9298 9307
6. M. Saikai, M. Ueda, and N. Miyaura Angew. Chem. Int. Ed. 37 1998 3279
7. M. Ueda, and N. Miyaura J. Org. Chem. 65 2000 4450
8. A. Fürstner, and H. Krause Adv. Synth. Catal. 343 2001 343
9. S. Uk Son, S. Bok Kim, J.A. Reingold, G.B. Carpenter, and D.A. Sweigart J. Am. Chem. Soc. 127 2005 12238 12239
10. G. Mora, S. Darses, and J.P. Genet Adv. Synth. Catal. 349 2007 1180 1184
11. P.Y. Toullec, R.B.C. Jagt, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Org. Lett. 8 13 2006 2715 2718
12. S.L.X. Martina, R.B.C. Jagt, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Chem. Commun. 2006 4093 4095
13. G.R. Ganci, and J.D. Chisholm Tetrahedron Lett. 48 2007 8266 8269
14. R.B.C. Jagt, P.Y. Toullec, D. Geerdink, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Angew. Chem. Int. Ed. 45 2006 2789 2791
15. H. Shimizu, and M. Murakami Chem. Commun. 2007 2855 2857
16. H.-F. Duan, J.-H. Xie, X.-C. Qiao, L.X. Wang, and Q.-L. Zhou Angew. Chem. Int. Ed. 47 2008 4351 4353
17. C.-H. Xing, T.-P. Liu, J.R. Zheng, J. Ng, M. Esposito, and Q.-S. Hu Tetrahedron Lett. 50 2009 4953 4957
18. M. Kuriyama, N. Ishiyama, R. Shimazawa, R. Shirai, and O. Onomura J. Org. Chem. 74 2009 9210 9213
19. R.B.C. Jagt, P.Y. Toullec, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Org. Biomol. Chem. 4 2006 773 775
20. T. Nishimura, H. Kumamoto, M. Nagaosa, and T. Hayashi Chem. Commun. 2009 5713 5715
21. T. Noël, K. Vandyck, and J. Van der Eycken Tetrahedron 63 2007 12961 12967
22. C. Defieber, H. Grützmacher, and E.M. Carreira Angew. Chem. Int. Ed. 47 2008 4482 4502 (Review)
23. Y. Yamamoto, K. Kurihara, and N. Miyaura Angew. Chem. Int. Ed. 48 2009 4414 4416
24. J. Bouffard, and K. Itami Org. Lett. 11 2009 4410 4413
25. H. Zheng, Q. Hang, J. Chen, M. Liu, S. Cheng, J. Ding, H. Wu, and W. Su J. Org. Chem. 74 2009 934 945
26. T. Zou, S.-S. Pi, and J.-H. Li Org. Lett. 11 2009 453 456
27. T. Hayashi, M. Takahashi, Y. Takaya, and M. Ogasawara J. Am. Chem. Soc. 124 2002 5052 5058
28. R.F. Heck, and P. Nolley Jr. J. Org. Chem. 37 14 1972 2320 2322
29. P. Zhao, C.D. Incarvito, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 3124 3125
30. T. Nishimura, T. Katoh, and T. Hayashi Angew. Chem. Int. Ed. 46 2007 4937 4939
31. C. Krug, and J.F. Hartwig Organometallics 23 2004 4594 4607
32. P. Zhao, and J.F. Hartwig Organometallics 27 2008 4749 4757
33. C. Krug, and J.F. Hartwig J. Am. Chem. Soc. 124 2002 1674 1679
34. T. Ishiyama, and J. Hartwig J. Am. Chem. Soc 122 2000 12043 12044
35. We did not consider the barrier for proton transfer in D to form species R.S., as this process is most likely solvent assisted. However, such proton transfer reactions are generally low barrier processes, and thus R.S. should be easily accessible from D.
36. R. Ahlrichs, M. Bär, H.-P. Baron, R. Bauernschmitt, S. Böcker, M. Ehrig, K. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Häser, C. Hättig, H. Horn, C. Huber, U. Huniar, M. Kattannek, A. Köhn, C. Kölmel, M. Kollwitz, K. May, C. Ochsenfeld, H. Öhm, A. Schäfer, U. Schneider, O. Treutler, K. Tsereteli, B. Unterreiner, M. von Arnim, F. Weigend, P. Weis, and H. Weiss Turbomole Version 5 January 2002 Theoretical Chemistry Group, University of Karlsruhe
37. O. Treutler, and R. Ahlrichs J. Chem. Phys. 102 1995 346 354
38. Turbomole basisset library, Turbomole Version 5, see.
39. A. Schäfer, H. Horn, and R. Ahlrichs J. Chem. Phys. 97 1992 2571 2577
40. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, and H. Preuss Theor. Chim. Acta 77 1990 123 141
41. A. Schäfer, C. Huber, and R. Ahlrichs J. Chem. Phys. 100 1994 5829 5835
42. R. Ahlrichs, and K. May Chem. Phys. 2 2000 943
43. PQS Version 2.4 2001 Parallel Quantum Solutions Fayetteville, AR, USA (the Baker optimizer is available separately from PQS upon request)
44. J. Baker J. Comput. Chem. 7 1986 385 395
45. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
46. A.D. Becke J. Chem. Phys. 98 1993 1372 1377
47. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
48. Calculations were performed using the Turbomole functional "b3-lyp", which is not identical to the Gaussian "B3LYP" functional.
49. A.L. Spek PLATON. A Multipurpose Crystallographic Tool 2003 Utrecht University Utrecht, The Netherlands