Counterion effect in the reaction mechanism of NHC gold(I)-catalyzed alkoxylation of alkynes: Computational insight into experiment

ACS Catalysis

Volumn 5, Issue 2, 2015, Pages 803-814

  Ciancaleoni, Gianluca ^a   Belpassi, Leonardo ^a   Zuccaccia, Daniele ^a,b   Tarantelli, Francesco ^a   Belanzoni, Paola ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF UDINE   (Italy)

Author keywords

Alkynes; Anion effect; DFT calculations; Homogeneous catalysis; N heterocyclic carbene gold complexes; Reaction mechanism

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; COMPLEXATION; COMPUTATION THEORY; DENSITY FUNCTIONAL THEORY; GOLD; GOLD COMPOUNDS; HYDROCARBONS; HYDROGEN BONDS; METHANOL; NEGATIVE IONS; ORGANIC COMPOUNDS; REACTION KINETICS;

ALKYNES; ANION EFFECTS; DFT CALCULATION; GOLD COMPLEXES; HOMOGENEOUS CATALYSIS; REACTION MECHANISM;

IONS;

EID: 84922734618     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501681f     Document Type: Article

References (56)

1. Haruta, M. Nature 2005, 437, 1098-1099 10.1038/4371098a
2. Nolan, S. P. Acc. Chem. Res. 2011, 44, 91-100 10.1021/ar1000764
3. Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729-3731 10.1021/jo00011a058
4. Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1418 10.1002/(SICI)1521-3773(19980605)37:10<1415::AID-ANIE1415>3.0.CO;2-N
5. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378 10.1021/cr068430g
6. Brouwer, C.; He, C. Angew. Chem., Int. Ed. 2006, 45, 1744-1747 10.1002/anie.200504495
7. Schelwies, M.; Dempwolff, A. L.; Rominger, F.; Helmchen, G. Angew. Chem., Int. Ed. 2007, 46, 5598-5601 10.1002/anie.200701378
8. Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 2079-2081 10.1021/ol800646h
9. Weber, D.; Jones, T. D.; Adduci, L.; Gagné, M. R. Angew. Chem., Int. Ed. 2012, 51, 2452-2456 10.1002/anie.201107659
10. Kovács, G.; Lledós, A.; Ujaque, G. Organometallics 2010, 29, 3252-3260 10.1021/om100063v
11. Tarselli, M. A.; Chianese, A. R.; Lee, S. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2007, 46, 6670-6673 10.1002/anie.200701959
12. Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940-6941 10.1021/ja802144t
13. Davies, P. W.; Martin, N. Org. Lett. 2009, 11, 2293-2296 10.1021/ol900609f
14. Gorin, D. J.; Watson, I. D. G.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736-3737 10.1021/ja710990d
15. Gorin, D. J.; Watson, I. D. G.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736-3737 10.1021/ja710990d
16. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496-499 10.1126/science.1145229
17. LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453 10.1021/ja068819l
18. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265 and references therein 10.1021/cr068434l
19. Jiménez-Nùnez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350 and references therein 10.1021/cr0684319
20. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211 10.1021/cr000436x
21. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994-2009 10.1021/cr1004088
22. Obradors, C.; Echavarren, A. M. Chem. Commun. 2014, 50, 16-28 10.1039/c3cc45518a
23. Zhdanko, A.; Maier, M. M. Angew. Chem., Int. Ed. 2014, 53, 7760-7764 10.1002/anie.201402557
24. Lein, M.; Rudolph, M.; Hashmi, A. S. K.; Schwerdtfeger, P. Organometallics 2010, 29, 2206-2210 10.1021/om900710v
25. Kovács, G.; Ujaque, G.; Lledós, A. J. Am. Chem. Soc. 2008, 130, 853-864 10.1021/ja073578i
26. Zhdanko, A.; Maier, M. M. Chem.-Eur. J. 2014, 20, 1918-1930 10.1002/chem.201303795
27. Roithovà, J.; Jankovà, Š Jašìkovà, L.; Vàňa, J.; Hybelbauerovà, S. Angew. Chem., Int. Ed. 2012, 51, 8378-8382 10.1002/anie.201204003
28. Oonishi, Y.; Gómez-Suárez, A.; Martin, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2013, 52, 9767-9771 10.1002/anie.201304182
29. Zhdanko, A.; Maier, M. E. ACS Catal. 2014, 4, 2770-2775 10.1021/cs500446d
30. Biasiolo, L.; Trinchillo, M.; Belanzoni, P.; Belpassi, L.; Busico, V.; Ciancaleoni, G.; D'Amora, A.; Macchioni, A.; Tarantelli, F.; Zuccaccia, D. Chem.-Eur. J. 2014, 20, 14594-14598 10.1002/chem.201404539
31. Bandini, M.; Bottoni, A.; Chiarucci, M.; Cera, G.; Miscione, G. P. J. Am. Chem. Soc. 2012, 134, 20690-20700 10.1021/ja3086774
32. Kim, J. H.; Park, S.-W.; Park, S. R.; Lee, S.; Kang, E. J. Chem.-Asian J. 2001, 6, 1982-1986 10.1002/asia.201100135
33. Zhow, T.; Xu, L.; Xia, Y. Org. Lett. 2013, 15, 6074-6077 10.1021/ol4029644
34. Macchioni, A. Chem. Rev. 2005, 105, 2039-2074 10.1021/cr0300439
35. Wang, Y.; Wang, Z.; Li, Y.; Wu, G.; Cao, Z.; Zhang, L. Nature Communication 2014, 5, 3470 DOI: 10.1038/ncomms4470
36. Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776-1782 10.1039/b711132k
37. Wang, W.; Kumar, M.; Hammond, G. B.; Xu, B. Org. Lett. 2014, 16, 636-639 10.1021/ol403584e
38. In the present work, the BArF? anion will not be considered because of its large size, its extremely low tendency to form ion pairs, and its inability to form HBs
39. Zuccaccia, D.; Bellachioma, G.; Cardaci, G.; Ciancaleoni, G.; Zuccaccia, C.; Clot, E.; Macchioni, A. Organometallics 2007, 26, 3930-3946 10.1021/om7003157
40. Krauter, C. M.; Hashmi, A. S. K.; Pernpointner, M. ChemCatChem. 2010, 2, 1226-1230 10.1002/cctc.201000136
41. Schmid, T. M.; Consiglio, G. Chem. Commun. 2004, 2318-2319 10.1039/b407843h
42. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864-B871 10.1103/PhysRev.136.B864
43. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-A1138 10.1103/PhysRev.140.A1133
44. Parr, R. G.; Yang, W. In Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
45. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41-51 10.1016/0301-0104(73)80059-X
46. Te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Guerra, C. F.; van Gisbergen, S. J. A. J. Comput. Chem. 2001, 22, 931-967 10.1002/jcc.1056
47. ADF User's Guide, Release 2013.01, SCM, Theoretical Chemistry, Vrije Universiteit: Amsterdam, The Netherlands, 2013; http://www.scm.com.
48. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100 10.1103/PhysRevA.38.3098
49. Perdew, J. P.; Wang, Y. Phys. Rev. B 1986, 33, 8822-8824 10.1103/PhysRevB.33.8822
50. van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1994, 101, 9783-9792 10.1063/1.467943
51. van Lenthe, E.; van Leeuwen, R.; Baerends, E. J.; Snijders, J. G. Int. J. Quantum Chem. 1996, 57, 281-293 10.1002/(SICI)1097-461X(1996)57:3<281::AID-QUA2>3.0.CO;2-U
52. Neese, F. WIREs Comput. Mol. Sci. 2012, 2, 73-78 10.1002/wcms.81
53. Grimme, S. J. Chem. Phys. 2006, 124, 034108 10.1063/1.2148954
54. Ciancaleoni, G.; Rampino, S.; Zuccaccia, D.; Tarantelli, F.; Belanzoni, P.; Belpassi, L. J. Chem. Theory Comput. 2014, 10, 1021-1034 10.1021/ct400980w
55. Kang, R. H.; Chen, H.; Shaik, S.; Yao, J. J. Chem. Theory Comput. 2011, 7, 4002-4011 10.1021/ct200656p
56. Kang, R. H.; Lai, W.; Yao, J.; Shaik, S.; Chen, H. J. Chem. Theory Comput. 2012, 8, 3119-3127 10.1021/ct3003942