Two distinct mechanisms of alkyne insertion into the metal-sulfur bond: Combined experimental and theoretical study and application in catalysis

Chemistry - A European Journal

Volumn 16, Issue 7, 2010, Pages 2063-2071

  Ananikov, Valentine P ^a   Gayduk, Konstantin A ^a   Orlov, Nikolay V ^a   Beletskaya, Irina P ^b   Khrustalev, Victor N ^c   Antipin, Mikhail Yu ^c  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Heterogeneous catalysis; Homogeneous catalysis; Insertion; Nickel; Stereoselectivity; Vinyl sulfides

Indexed keywords

ALKYNE INSERTIONS; BOND FORMATION; CARBON-CARBON BOND; CATALYTIC CYCLES; CATALYTIC REACTIONS; CATALYTIC SYSTEM; COST-EFFICIENT; HETEROGENEOUS CATALYSIS; HIGH YIELD; HOMOGENEOUS CATALYSIS; INSERTION; INTERNAL ALKYNES; LIGAND DISSOCIATION; METAL-SULFUR BONDS; REDUCTIVE ELIMINATION; STEREO-SELECTIVE; SYNTHETIC PROCEDURES; THEORETICAL INVESTIGATIONS; THEORETICAL STUDY;

ACETYLENE; DISSOCIATION; LIGANDS; METAL COMPLEXES; METALS; NICKEL ALLOYS; REACTION KINETICS; STEREOSELECTIVITY; SULFUR;

CATALYSIS;

EID: 76449099135     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902928     Document Type: Article

References (88)

1. a) Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001;
2. b) M. Beller, J. Seayad, A. TiIlack, H. Jiao, Angew. Chem. 2004, 116, 3448;
3. Angew. Chem. Int. Ed. 2004, 43, 3368;
4. c) T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205;
5. d) I. Beletskaya, C. Moberg, Chem. Rev. 2006, 106, 2320;
6. e)F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079;
7. f)M. Suginome, Y. Ito, J. Organomet. Chem. 2003, 685, 218;
8. g) M. Suginome, Y. Ito, J. Organomet. Chem. 2003, 680, 43;
9. h) A. Ogawa, J. Organomet. Chem. 2000, 611, 463;
10. i D. M. Ide, M. P. Eastlund, C. L. Jupe, R. A. Stockland, Jr., Curr. Org. Chem. 2008, 12, 1258.
11. L. L. Hegedus, R. W. McCabe, Catalyst Poisoning, Marcel Dekker, New York, 1984.
12. I. P. Beletskaya, V. P. Ananikov, Eur. J. Org. Chem. 2007, 3431.
13. a) H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1992, 114, 5902;
14. b) A. Ogawa, T. Ikeda, K. Kimura, T. Hirao, J. Am. Chem. Soc. 1999, 121, 5108.
15. V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Adv. Synth. Catal. 2005, 347,1993.
16. a) C. Cao, L. R. Fraser, J. A. Love, J. Am. Chem. Soc. 2005, 127, 17614;
17. b) Y. Misumi, H. Seino, Y. Mizobe, J. Organomet. Chem. 2006, 691, 3157;
18. c) S. Shoai, P. Bichler, B. Kang, H. Buckley, J. A. Love, Organometallics 2007, 26, 5778;
19. d) L. R. Fraser, J. Bird, Q. Wu, C. Cao, B. O. Patrick, J. A. Love, Organometallics 2007, 26, 5602;
20. e) S. Burling, L. D. Field, B. A. Messerle, K. Q. Vuong, P. Turner, J. Chem. Soc. Dalton Trans. 2003, 4181.
21. a) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, Organometallics 2006, 25, 1970;
22. b) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, Organometallics 2007, 26, 740.
23. V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev, M. Yu. Antipin, T. V. Timofeeva, J. Am. Chem. Soc. 2007, 129, 7252.
24. In the absence of the phosphine ligand another mechanism may take place involving protonolysis as a product formation step (Scheme 2). See reference [3] for discussion of various mechanistic details. In any case, alkyne coordination and insertion remain as the key steps in all reported reactions.
25. Only mononuclear transition metal complexes are shown on the scheme for clarity reasons, see reference [3,12] for more details.
26. H. Kuniyasu, A. Ogawa, S. Miyazaki, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1991, 113, 9796.
27. a) V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Organometallics 2003, 22, 1414;
28. b) V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, V. N. Khrustalev, M. Yu. Antipin, Organometallics 2005, 24, 1275.
29. H. Kuniyasu, F. Yamashita, J. Terao, N. Kambe, Angew. Chem. 2007, 119, 6033;
30. Angew. Chem. Int. Ed. 2007, 46, 5929.
31. a) M. Arisawa, M. Yamaguchi, Org. Lett. 2001, 3, 763;
32. b) M. Arisawa, Y. Kozuki, M. Yamaguchi, J. Org. Chem. 2003, 68, 8964.
33. I. P. Beletskaya, V. P. Ananikov, Pure. Appl. Chem. 2007, 79, 1041.
34. a) V. P. Ananikov, I. P. Beletskaya, Russ. Chem. Bull. 2004, 53, 561;
35. b) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, Russ. Chem. Bull. 2005, 54, 576.
36. V. P. Ananikov, I. P. Beletskaya, Org. Biomol. Chem. 2004, 2, 284.
37. V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, Synlett 2005, 1015.
38. V. P. Ananikov, K. A. Gayduk, I. P. Beletskaya, V. N. Khrustalev, M. Yu. Antipin, Chem. Eur. J. 2008, 14, 2420.
39. a) I. Kamiya, J. Kawakami, S. Yano, A. Nomoto, A. Ogawa, Organometallics 2006, 25, 3562;
40. b)W Zheng, A. Ariafard, Z. Lin, Organometallics 2008, 27, 246.
41. H. Kuniyasu, K. Takekawa, F. Yamashita, K. Miyafuji, S. Asano, Y. Takai, A. Ohtaka, A. Tanaka, K. Sugoh, H. Kurosawa, N. Kambe, Organometallics 2008, 27, 4788.
42. V. P. Ananikov, N. V. Orlov, M. A. Kabeshov, I. P. Beletskaya, Z. A. Starikova, Organometallics 2008, 27, 4056.
43. Selected references on the application of the vinyl sulfides as building blocks in organic synthesis, as ligands in catalysis and structural motifs in material science: a) G. Matsubayashi, M. Nakano, H. Tamura, Coord. Chem. Rev. 2002, 220, 143;
44. b)N. Robertson, L. Cronin, Coord. Chem. Rev. 2002, 227, 93;
45. c) M. Fourmigué, Acc. Chem. Res. 2004, 37, 179;
46. d) A. Kobayashi, E. Fujiwara, H Kobayashi, Chem. Rev. 2004, 104, 5243;
47. e) R. Kato, Chem. Rev. 2004, 104, 5319;
48. f) UT. Mueller-Westerhoff, B. Vance, D. I. Yoon, Tetrahedron 1991, 47, 909;
49. g) S. D. P. Baugh, Z. Yang, D. K. Leung, D. M. Wilson, R. Breslow, J. Am. Chem. Soc. 2001, 123, 12488;
50. h) B. J. Vesper, K. Salaita, H. Zong, C. A. Mirkin, A. G. M. Barrett, B. M. Hoffman, J. Am. Chem. Soc. 2004, 126, 16653;
51. h) S. Belviso, G. Ricciardi, F. Lelj, J. Mater. Chem. 2000, 10, 297;
52. i) S. H. Eichhorn, D. W. Bruce, D. Guillon, J.-L. Gallani, T. Fischer, J. Stumpe, T. Geue, J. Mater. Chem. 2001, 11, 1576;
53. j) F. Bonosi, G. Ricciardi, F. Lelj, G. Martini, J. Phys. Chem. 1994, 98, 10613;
54. k) S. B. Sesalan, A. Gul, Monatsh. Chem. 2000, 131, 1191;
55. l) H. Braun, A. Amann, Angew. Chem. 1975, 87, 113;
56. Angew. Chem. Int. Ed. Engl. 1975, 14, 755;
57. m) M. E. Garst, P. Arrhenius, J. Org. Chem. 1983, 48, 16.
58. a) P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Academic Press, New York, 1974;
59. b) "Polymerization of Acetylenes": T. Masuda, F. Sanda, M. Shiotsuki in Comprehensive Organometallic Chemistry III, Vol.11 (Eds.: D. M. P. Mingos, R. H. Crabtree), Elsevier, Oxford, 2007, pp. 557-593.
60. 3 ligand a slightly lower yield was observed due to byproducts formation through the known mechanism involving benzenethiol conversion to diphenyl disulfide (see ref. [5]).
61. [1,3].This rules out an alternative route involving external attack of the sulfur group, which results in formation of anii'-addition products with E configuration of the double bond.
62. See the Supporting Information for detailed description of X-ray study and geometry parameters.
63. See Figure Sl in the Supporting Information for the optimized structures I, II-TS, IV, V, VI-TS, and VIII.
64. -1 relative to IV and VIII, respectively.
65. For a related discussion of the influence of in-plane and out-ofplane ligand orientation on C-C reductive elimination see: a) V. P. Ananikov, D. G. Musaev, K. Morokuma, J. Am. Chem. Soc. 2002, 124, 2839;
66. b) V. P. Ananikov, D. G. Musaev, K. Morokuma, Organometallics 2005, 24, 715;
67. c) V. P. Ananikov, D. G. Musaev, K. Morokuma, Eur. J. Inorg. Chem. 2007, 5390.
68. R. Ghosh, X. Zhang, P. Achord, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2007, 129, 853.
69. In addition to product 3a (≈50%) the formation of 1,3-dienes was also observed according to a known reaction. Both reactions-formation of alkene 3 a and dienes-involve alkyne insertion and re- ductive elimination steps (see ref. [22] for the discussion of the mechanism of dienes formation).
70. [12,17,19] At the moment it is impossible to separate unambiguously these two types of the ligand effects and to estimate their contribution to the overall performance enhancement of the studied catalytic reaction. In any case, it is clear that the pathway involving alkyne coordination to the apical Ni site without the need of phosphine ligand dissociation better agrees with the results of the NMR monitoring.
71. a) D. S. Pedersen, C. Rosenbohm, Synthesis 2001, 2431;
72. b) L. M. Harwood, Aldrichim. Acta 1985, 18, 25.
73. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
74. Priroda, an electronic structure code program, D. N. Laikov Moscow State University, Moscow (Russia), 2004.
75. a) D. N. Laikov, Chem. Phys. Lett. 1997, 281, 151;
76. b) D. N. Laikov, Chem. Phys. Lett. 2005, 416, 116.
77. Some selected recent examples: a) N. M. Logacheva, V. E. Baulin, A. Yu. Tsivadze, E. N. Pyatova, I. S. Ivanova, Y. A. Velikodny, V. V. Chernyshev, Dalton Trans. 2009, 2482;
78. b) A. A. Popov, A. V. Burtsev, V. M. Senyavin, L. Dunsch, S. I. Troyanov, J. Phys. Chem. A 2009, 113, 263;
79. c) J. R. Khusnutdinova, L. L. Newman, P. Y. Zavalij, Y.-F. Lam, A.N. Vedernikov, J. Am. Chem. Soc. 2008, 130, 2174
80. A. A. Popov, L. Dunsch, J. Am. Chem. Soc. 2008, 130, 17726;
81. e) A. Yahav-Levi, I. Goldberg, A. Vigalok, A. N. Vedernikov, J. Am. Chem. Soc. 2008, 130, 724;
82. f) G. A. Shamov, G. Schreckenbach, R. L. Martin, P. J. Hay, Inorg. Chem. 2008, 47, 1465;
83. g) J. J. Berard, G. Schreckenbach, P. L. Arnold, D. Patel, J. B. Love, Inorg. Chem. 2008, 47, 11583;
84. h) S. Sanz, L. A. Jones, F. Mohr, M. Laguna, Organometallics 2007, 26, 952;
85. i) G. A. Shamov, G. Schreckenbach, J. Phys. Chem. A 2006, 110, 9486;
86. j) E. N. Esenturk, J. Fettinger, B. Eichhorn, J. Am. Chem. Soc. 2006, 128, 9178;
87. k)Y. Smurnyy, C. Bibal, M. Pink, K. G. Caulton, Organometallics 2005, 24, 3849;
88. C. Bibal, Y. D. Smurnyy, M. Pink, K. G. Caulton, J. Am. Chem. Soc. 2005, 127, 8944.