Efficient intramolecular hydroalkoxylation of unactivated alkenols mediated by recyclable lanthanide lriflate ionic liquids: Scope and mechanism

Chemistry - A European Journal

Volumn 16, Issue 11, 2010, Pages 3403-3422

  Dzudza, Alma ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Alkenols; Hydroalkoxylation; Ionic liquids; Lanthanide triflates; Reaction mechanisms

Indexed keywords

ACTIVATION PARAMETER; ALKENOLS; ALKOXIDES; BENZOFURANS; CATALYTIC PATHWAYS; CONTROLLED TRANSITIONS; CYCLIC TRANSITIONS; CYCLIZATION RATES; CYCLIZATIONS; ELECTRON-DEFICIENT; FUNCTIONALIZED; HYDROALKOXYLATION; IMIDAZOLIUM; INTRAMOLECULAR PROTON TRANSFER; IONIC RADIUS; KINETIC ISOTOPE EFFECTS; LANTHANIDE TRIFLATES; LANTHANIDES; NUCLEOPHILIC ATTACK; OVERALL RATE; RATE DEPENDENCE; REACTION COORDINATES; REACTION MECHANISM; RECYCLABLE CATALYST; RING CLOSURES; ROOM TEMPERATURE IONIC LIQUIDS; TRANSITION STATE; TRIFLIC ACIDS; TURNOVER FREQUENCY;

CYCLIZATION; IONIZATION OF LIQUIDS; IONS; ISOTOPES; OLEFINS; PROTONS; YTTERBIUM;

IONIC LIQUIDS;

EID: 77949291993     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902269     Document Type: Article

References (200)

1. a) K. Tani, V. Kataoka in Catalytic Heterofunctionalization, Vol.2 (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, pp. 171-216.
2. a) M. C. Elliott, E. Williams, J. Chem. Soc. Perkin Trans. 1 2001, 2303-2340;
3. b) Z.-Y. Yao, H.-P. Wu, Y.-L. Wu, J. Med. Chem. 2000, 43, 2484-2487;
4. (c) A. Mitchenson, A. Nadin, J. Chem. Soc. Perkin Trans. 1 2000, 2862-2892;
5. (d) M. C. Elliott, J. Chem. Soc. Perkin Trans. 1 2000, 1291-1318;
6. e) T. L. B. Boivin, Tetrahedron 1987, 43, 3309-3362;
7. f) P. A. Bartlett, Tetrahedron 1980, 36, 272.
8. a) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004, pp. 27-103;
9. b) T. Pei, X. Wang, R. A. Widenhoefer, J. Am. Chem. Soc. 2003, 125, 648-649;
10. (c) K. Muñz, Adv. Synth. Catal 2004, 346, 1425-1428;
11. (d) Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, S. Yamaguchi, J. Org. Chem. 1997, 62, 116-777;
12. e) M. Rönn, J. E. Bäckvall, P. G. Andersson, Tetrahedron Lett. 1995, 36, 7749-7752.
13. For examples of Brønsted acid mediated alkene hydroalkoxylation, see: a) D. C. Rosenfeld, S. Shekhar, A. Tameiyama, M. Utsunomiya, J. F. Hartwig, Org. Lett. 2006, 8, 4179-41.82;
14. b) L. Coulombel, E. Dufiach, Green Chem. 2004, 6, 499-501;
15. (c) B. Wang, Y. Gu, L. Yang, J. Suo, O. Kenichi, Catal. Lett. 2004, 96, 71-74;
16. (d) P.J. Linares-Palomino, S. Salido, J. Altarejos, A. Sánchez, Tetrahedron Lett. 2003, 44, 6651-6655.
17. For examples of transition-metal-mediated alkene hydroalkoxylation, see: a) C.-G. Yang, C. He, J. Am. Chem. Soc. 2005, 127, 6966-6967;
18. b) Y. Oe, T. Ohta, Y. Ito, Synlett 2005, 179-181;
19. (c) Y. Oe, T. Ohta, Y. Ito, Chem. Commun. 2004, 1620-1621;
20. (d) H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 9536-9537;
21. e) E. Marotta, E. Foresti, T. Marcelli, F. Peri, P. Righi, N. Scardovi, G. Rosini, Org. Lett. 2002, 4, 4451-4453;
22. f) K. Hori, H. Kitagawa, A. Miyoshi, T. Ohta, T. I. Furukawa, Chem. Lett. 1998, 1083-1.084;
23. g) K. Hori, H. Kitagawa, A. Miyoshi, T. Ohta, T. I. Furukawa, Chem. Lett. 1998, 1083-1084.
24. For examples of metal-triflate-mediated alkene hydroalkoxylation, see: a) K. Komeyama, T. Morimoto, Y. Nakayama, K. Takaki, Tetrahedron Lett. 2007, 48, 3259-3261;
25. b) L. Coulombel, M. Rajzmann, J.-M. Pons, S. Olivero, E. Dufiach, Chem. Eur. J. 2006, 12, 6356-6365;
26. (c) C.-G. Yang, N. W. Reich, C. He, Org. Lett. 2005, 7, 4553-4556;
27. (d) C.-G. Yang, N. W. Reich, Z. Shi, C. He, Org. Lett. 2005, 7, 4553-4556.
28. For examples of lanthanide-mediated alkyne and aliene hydroalkoxylation, see: a) S. Seo, X. Yu, T.J. Marks, J. Am. Chem. Soc. 2009, 131, 263-276;
29. b) X. Yu, S. Seo, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 7244-7245;
30. (c) S. Seo, T. J. Marks, Chem. Eur. J. 2010, in press DOI: 10.1002/chem.200903027.
31. a) F. Alonso, I. P. Beletsaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159;
32. b)M. A. Tius in Modern Allene Chemistry, Vol.2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 834-838;
33. (c) P. A. Bartlett in Asymmetric Synthesis, Vol.3 (Ed.: J. D. Morrisson), Academic Press, New York, 1984, p. 455.
34. Baldwin 3- to 7-membered ring-closure rules: a) J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-735;
35. b) J. E. Baldwin, R. C. Thomas, L. I. Kruse, L. Silberman, J. Org. Chem. 1977, 42, 3846-3852.
36. J. G. Taylor, H. Whithall, K. K. M. Hii, Chem. Commun. 2005, 5103.
37. T. Hosokawa, T. Shinohara, Y. Ooka, S.-I. Murahashi, Chem. Lett. 1989, 2001-2004.
38. For recent organolanthanide reviews, see: a) S. B. Amin, T. J. Marks, Angew. Chem. 2008, 120, 2034-2054;
39. Angew. Chem. Int. Ed. 2008, 47, 2006-2025;
40. b) H. C. Aspinall, Chem. Rev. 2002, 102, 1807-1850;
41. (c) F. T. Edelmann, D. M. M. Freckmann, H. Schumann, Chem. Rev. 2002, 102, 1851-1896;
42. (d) G. A. Molander, A.C. Romero, Chem. Rev. 2002, 102, 2161-2186;
43. e) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2210;
44. f) F. T. Edelmann in Comprehensive Organometallic Chemistry, Vol.4 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon Press, Oxford, 1995, Chapter 2;
45. g) T. J. Marks, R. D. Ernst in Comprehensive Organometallic Chemistry (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon Press, Oxford, 1982, Chapter 21.
46. For lanthanide-mediated hydroamination, see: a) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673-686;
47. b) J.-S. Ryu, T. J. Marks, F. E. McDonald, J. Org. Chem. 2004, 69, 1038-1052;
48. (c) J.-S. Ryu, Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12584-12605;
49. (d) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886-7887;
50. e) J.-S. Ryu, T. J. Marks, F. E. McDonald, Org. Lett. 2001, 3, 3091-3094;
51. f) V. M. Arredondo, F. E. McDonald, T. J. Marks, Organometallics 1999, 18, 1949-1960;
52. g) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 1757-1771;
53. h) Y. Li, T. J. Marks, Organometallics 1996, 15, 3770-3772;
54. (i) C.M. Haar, C. L. Stern, T. J. Marks, Organometallics 1996, 15, 1765-1775;
55. j) Y. Li, T. J. Marks, Organometallics 1994, 13, 439-440;
56. k)M.R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275-294.
57. For lanthanide-mediated hydrophosphination, see: a) A. M. Kawaoka, M. R. Douglass, T. J. Marks, Organometallics 2003, 22, 46304632;
58. b) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283-292;
59. (c) M. R. Douglass, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 2001, 123, 10221-10238.
60. For lanthanide-mediated hydrosilylation and hyboration, see: a) P.F. Fu, L. Brard, Y. Li, T. J. Marks, J. Am. Chem. Soc. 1995, 117, 7157-7168;
61. b) K. N. Harrison, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 9220-9221.
62. Y. Li, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 1757-1771.
63. a) S. B. Amin, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 10102-10103;
64. b) A. M. Kawaoka, T. J. Marks, J. Am. Chem. Soc. 2005, 127, 6311-6324;
65. (c) V. C. Gibson, S. K. Spitzmesser, Chem. Rev. 2003, 103, 283-31.6;
66. (d) Y.-X. Chen, T. J. Marks, Chem. Rev. 2000, 100 (special issue on "Frontiers in Metal-Catalyzed Polymerization").
67. a) S. P. Nolan, D. Stern, T.J. Marks, J. Am. Chem. Soc. 1989, 111, 7844-7853;
68. b) D. F. McMillen, D.M. Golden, Annu. Rev. Phys. Chem. 1982, 33, 493-532;
69. (c) S. W. Benson, Thermochemical Kinetics, 2nd ed., Wiley, New York, 1976, Appendix Tables A10, 11, and 22;
70. (d) M. A. Giardello, W. A. King, S. P. Nolan, M. Porchia, C. Sishta, T. J. Marks in Energetics of Organometallic Species (Ed.: J. A. Martinho Simoes), Kluwer Academic, Dordrecht, 1992, pp. 35-54;
71. e) M. R. Gagné, S. P. Nolan, A. M. Seyan, D. Stern, T. J. Marks in Metal-Metal Bonds and Clusters in Chemistry and Catalysis (Ed.: J. P. Fackler, Jr.), Plenum Press, New York, 1990, pp. 113-125;
72. f) T. J. Marks in Bonding Energetics in Organometallic Compounds (Ed.: T. J. Marks), ACS Symposium Series 428, American Chemical Society, Washington, DC, 1990, pp. 1-18;
73. g) S. P. Nolan, D. Stern, D. Hedden, T. J. Marks in Bonding Energetics In Organometallic Compounds (Ed.: T. J. Marks), ACS Symposium Series 428, American Chemical Society, Washington, DC, 1990, pp. 159-174.
74. 3]-mediated reactions: a) C. J. Li, L. Chen, Chem. Soc. Rev. 2006, 35, 6882;
75. b) S. Luo, L. Zhu, A. Ralukdar, G. Zhang, X. Mi, J. P. Chen, P. G. Wang, Mini-Rev. Org. Chem. 2005, 2, 177-202;
76. (c) C. Li, Chem, Rev. 2005, 105, 3095-3165;
77. (d) S. Kobayashi, Chem. Rev. 2002, 102, 2227-2302;
78. e) Lanthanides: Chemistry and Use in Organic Synthesis, Series: Topics in Organometallic Chemistry, Vol.2 (Ed.: S. Kobayashi), Springer, Berlin, 1999, Chapter 2.
79. Lanthanide chemistry: a) T. Imamoto, Lanthanides in Organic Synthesis, Academic Press, San Diego, 1.994;
80. b) S. Cotton, Lanthanide and Actinide Chemistry, Wiley, Chichester, England, 2006;
81. (c) H. C. Aspinall, Chemistry off-Elements, Gordon and Breach Science Publishers, Amsterdam, Netherlands, 2001;
82. (d) Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrman), Wiley, New York, 1998.
83. a) G. A. Molander, Chem. Rev. 1992, 92, 2968;
84. b) G. Lawrence, Chem. Rev. 1986, 86, 1733.
85. 3]-mediated C-C bond-forming reactions: a) S. Kobayashi, I. Hachiya, J. Org. Chem. 1994, 59, 3590-3596;
86. b)J. B. F. N. Engberts, J. W. Wijnen, J. Org. Chem. 1997, 62, 2039-2044;
87. (c) C. Bellucci, P. G. Cozzi, A. Umani-Ronchi, Tetrahedron Lett. 1995, 36, 7289-7292.
88. C. Reichardt in Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003.
89. a) Ionic Liquids HIB: Fundamentals, Progress, Challenges, and Opportunities, ACS Symposium Series 902 (Eds.: R. D. Rogers, K. R. Seddon), American Chemical Society, Washington DC, 2005;
90. b) Ionic Liquids 111 A: Fundamentals, Progress, Challenges, and Opportunities, ACS Symposium Series 901 (Eds.: R. D. Rogers, K. R. Seddon), American Chemical Society, Washington DC, 2005;
91. (c) Ionic Liquids: Industrial Applications to Green Chemistry, ACS Symposium Series 818 (Eds.: R. D. Rogers, K. R. Seddon), American. Chemical Society, Washington DC, 2002.
92. a) V. I. Parvulescu, C Hardacre, Chem. Rev. 2007, 107, 2615-2665;
93. b) K. Binnemans, Chem. Rev. 2007, 107, 2592-261.4;
94. (c) J. B. Harper, M. N. Kobrak, Mini-Rev. Org. Chem. 2006, 3, 253-269;
95. (d) V. A. Cocalia, K. E. Gutowski, R. D. Rogers, Coord. Chem. Rev. 2006, 250, 755-764;
96. e) J. Dupont, P. A. Z. Suarez, Phys. Chem. Chem. Phys. 2006, 8, 244.1-2452;
97. f) J. Dupont, R. F. de Souze, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692;
98. g) R. Sheldon, Chem. Commun. 2001, 23, 2399-2407;
99. h) P. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926-3945;
100. Angew. Chem. Int. Ed. 2000, 39, 3772-3789;
101. (i) T. Welton, Chem. Rev. 1999, 99, 2071-2083.
102. a) T. Singh, A. Kumar, J. Phys. Chem. B 2008, 112, 12968-12972;
103. b) H. Weingärtner, Phys. Chem. 2006, 220, 1395-1405;
104. (c) F. V. Bright, G. A. Baker, J. Phys. Chem. B 2006, 110, 5822-5823;
105. (d) T. Koddermann, C. Wertz, A. Heintz, R. Ludwig, Angew. Chem. 2006, 118, 3780-3785;
106. Angew. Chem. Int. Ed. 2006, 45, 3697-3702;
107. e) C. Wakai, A. Oleinikova, M. Ott, H. Weingärtner, J. Phys. Chem. A 2005, 109, 17028-17030;
108. f) A. Kawai, T. Hidemori, K. Shibuya, Chem. Lett. 2004, 33, 1464-1465.
109. a) K.-S. Yeung, M. E. Farkas, Z. Qiu, Z. Yang, Tetrahedron Lett. 2002, 43, 5793;
110. b) J. A. Boon, J. A. Levisky, J. L. Pflug, J. S. Wilkes, J. Org. Chem. 1986, 51, 480.
111. a) S. V. Dzyuba, R. A. Bartsch, Tetrahedron Lett. 2002, 43, 4657-4659;
112. b) P. Ludley, N. Karodia, Tetrahedron Lett. 2001, 42, 2011-2014;
113. (c) M. J. Earle, P. B. McCormac, K. R. Seddon, Green Chem. 1999, 40, 2325;
114. (d) T. Fisher, A. Sethi, T. Welton, J. Wolf, Tetrahedron Lett. 1999, 40, 793-796.
115. a) C. J. Mathews, P. J. Smith, T. Welton, Chem. Commun. 2000, 1249-1250;
116. b) C. J. Mathews, P.J. Smith, T. Welton, A. J. P. White, D. J. Williams, Organometallics 2001, 20, 3848-3850.
117. a) P. E. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. de Souza, J. Dupont, Polyhedron 1996, 15, 1217-1219;
118. b) L. Mußmann, H. Olivier, Y. Chauvin, Angew. Chem. 1995, 107, 2941-2943;
119. Angew. Chem. Int. Ed. Engl. 1995, 34, 2698-2700;
120. (c) C. E. Song, E. J. Roh, Chem. Commun. 2000, 837-838;
121. (d) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092.
122. A. Dzudza, T. J Marks, Org. Lett. 2009, 11, 1523-1526.
123. Thorpe-Ingold effect: a) S. M. Bachrach, J. Org. Chem. 2008, 73, 2466-2468;
124. b) P.G. Sammes, D. J. Weiler, Synthesis 1995, 12051222.
125. a) G. A. Olah, P. V. Reddy, G. K. Prakash, Chem. Rev. 1992, 92, 6995;
126. b) H. N. C. Wong, M. Y. Hon, C. W. Tse, Y. C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165-198;
127. (c) M. Brookhart, W.B. Studabaker, Chem. Rev. 1987, 87, 411-432.
128. R. D. Shannon, Acta Crystallogr. Sect. A 1976, 32, 751-767.
129. a)S. W Benson, Thermochemical Kinetics, 2nd ed., Wiley, New York, 1986, pp. 810;
130. b) P. J. Robinson, J. Chem. Educ. 1978, 55, 509-510;
131. (c) P. M. Morse, M. D. Spencer, S. R. Wilson, G. S. Girolami, Organometallics 1994, 13, 1646-1655.
132. Parameters in parentheses represent three values derived from the least-squares fit.
133. a) R. P. Bell, The Proton in Chemistry, 2nd ed., Cornell University Press, Ithaca, New York, 1973, Chapter 12;
134. b) L. Melander, W. H. Saunders, Jr., Reaction Rates of Isotopic Molecules, Wiley, New York, 1980.
135. J. L. McBee, A. T. Bell, D. T. Tilley, J. Am. Chem. Soc. 2008, 130, 16562-16571.
136. For proton traps, see: a) T. Saupe, H. A. Staab, Angew. Chem. 1988, 100, 895-909;
137. Angew. Chem. Int. Ed. Engl. 1988, 27, 865-1008;
138. b) R. W. Alder, M. R. Bryce, N. C. Goode, J. Chem. Soc. Perkin Trans. 2 1982, 477-483;
139. (c) A. Awwal, F. Hibbert, J. Chem. Soc. Perkin Trans. 2 1982, 1589-1592;
140. (d) B. Kanner, H. C. Brown, J. Am. Chem. Soc. 1966, 88, 986-992.
141. a) M. H. Alizadeh, H. Razavi, F. F. Bamoharram, K. Daneshvar, J. Mol. Catal. A 2003, 206, 89-93;
142. b) A. Alvanipour, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1980, 201, 233-247;
143. (c) R. W. Bott, C. Eaborn, P. M. Greasley, J. Chem. Soc. 1964, 4804-4806.
144. B. Xu, M. Shi, Org. Lett. 2002, 4, 2145-2148.
145. a) C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd ed., Bell, London, 1969;
146. b) E. D. Hughes, C. K. Ingold, J. Chem. Soc. 1935, 244;
147. (c) E. D. Hughes, Trans. Faraday Soc. 1941, 37, 603631;
148. (d) E. D. Hughes, C. K. Ingold, Trans. Faraday Soc. 1941, 37, 657-685;
149. e) K. A. Cooper, M. L. Dhar, E. D. Hughes, C. K. Ingold, B. J. MacNulty, L. I. Woolf, J. Chem, Soc. 1948, 2043-2049.
150. J. L. Anderson, J. Ding, T. Welton, D. W. Armstrong, J. Am. Chem. Soc. 2002, 124, 14247-14254.
151. 3+-arene complexes, see: a) H. Liang, Q. Shen, J. Guan, Y. Lin, J. Organomet. Chem. 1994, 474, 113-116;
152. b) G. B. Deacon, Aust. J. Chem. 1990, 43, 1245-1257;
153. (c) B. Fan, Q. Shen, Y. Lin, J. Organomet. Chem. 1989, 376, 6166;
154. (d) B. Fan, Q. Shen, Y. Lin, J. Organomet. Chem. 1989, 377, 5158;
155. e) A. Cotton, W. Schwotzer, Organometallics 1987, 6, 1275-1279;
156. f) A. Cotton, W. Schwotzer, J. Am. Chem. Soc. 1986, 108, 4657-14568
157. a) A. Motta, I. L. Fragala, T. J. Marks, Organometallics 2006, 25, 5533-5539;
158. b)A. Motta, I. L. Fragala, T.J. Marks, Organometallics 2005, 24, 4995-5003;
159. (c) A. Motta, G. Lanza, I. A. Fragala, T. J. Marks, Organometallics 2004, 23, 4097-4114;
160. (d) A. Motta, G. Lanza, I. L. Fragala, T. J. Marks, Organometallics 2004, 23, 4097-4104;
161. e) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933-2935.
162. a) R. Breslow in Molecular Rearrangements (Ed.: P. de Mayo), Interscience, New York, 1963, pp. 233-294;
163. b) P.H. Mazzocchi, H. J. Tamburin, J. Am. Chem. Soc. 1970, 92, 7220-7221.
164. a) J. Muzart, Tetrahedron 2008, 64, 5955-6008;
165. b) M. R. Gagné, S. J. Lee, A. R. Chianese, Angew. Chem. 2007, 119, 4118-4136;
166. Angew. Chem. Int. Ed. 2007, 46, 4042-4059;
167. (c) C. Munro-Leighton, S. A. Delp, E. D. Blue, B. T. Gunnoe, Organometallics 2007, 26, 1483-1493;
168. (d) J. Muzart, Tetrahedron 2005, 61, 5815-5849;
169. e) Transition Metals for Organic Synthesis, Vols. 1,2 (Eds.: M. Beller, C. BoIm), Wiley-VCH, Weinheim, 2004;
170. f) H. Jiao, A. Tillack, J. Seayad, M. Beller, Angew. Chem. 2004, 116, 3448-3479;
171. Angew. Chem. Int. Ed. 2004, 43, 3368-3398;
172. g) E. Hahn, Chem. Eur. J. 2004, 10, 5888-5899;
173. h) L. S. Hegedus in Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1999;
174. (i) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-704;
175. j) J. P. Coliman, L. S. Hegedus, J. R. Norton, R. G. Finke in Principles and Applications of Organotransition Metal Chemistry (Ed.: A. Kelly), University Science Books, Mill Valley, 1987.
176. a) I. Bertini, C. Luchinat, Coordination Chemistry Reviews: NMR. of Paramagnetic Substances, Vol.150 (Ed.: A. B. P. Lever), Elsevier, Netherlands, 1996, Chapter 19;
177. b) B. R. McGarvey, Can. J. Chem, 1984, 62, 1349-1355;
178. (c) B. R. McGarvey, J. Chem, Phys. 1976, 65, 955-961;
179. (d) W. D. Luke, A. Streitwieser, Jr., ACS Symp. Ser. 1980, 131, 93-140;
180. e) W. D. Horrocks, Jr., NMR of Paramagnetic Molecules (Eds.: G. N. La Mar, W. D. Horrocks, R. H. Holm), Academic Press, New York, 1973, Chapter 4.
181. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.
182. A. E. Hill, D. C. Link, P. Donndelinger, J. Org. Chem. 1981, 46, 1177-1182.
183. M. Bradley, P. J. May, D. C. Harrowven, Tetrahedron Lett. 2003, 44, 503-506.
184. T. Okazaki, Y. Maeda, T. Sugai, K. Mori, Tetrahedron 1985, 41, 307311.
185. P., Teijón, L. M, Burón, R. R. Clemente, R. R. González, A. Fernández-Mateos, J. Org. Chem, 2007, 72, 9973-9982.
186. P. S. Engel, A. M. Culotta, J. Am. Chem. Soc. 1991, 113, 2686-2696.
187. A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 60426043.
188. S.M. Perala, B. P. Conrad, C. A. Hughey, J. A. Shugart, G.W. Breton, Molecules 2001, 6, 655-662.
189. P. Yates, T. S. Macas, Can. J. Chem. 1988, 66, 110.
190. M. C. Marcotullio, V. Campagna, S. Sternativo, F. Constantini, M. Curini, Synthesis 2006, 2760-2766.
191. B. Janza, A. Studer, Org. Lett. 2006, 8, 1875-1878.
192. E. C. Ashby, R. N. DePriest, A. B. Goel, B. Wenderoth, T. N. Pham, J. Org. Chem. 1984, 49, 3545-3556.
193. a) A. Dzudza, T. J. Marks, J. Org. Chem. 2008, 73, 4004-4016;
194. b)J. L. Pascal, M. M. Hamidi, Polyhedron 1994, 13, 1787-1792;
195. (c) A. Abbasi, P. Lindqvist-Reis, L. Eriksson, D. Sandstrom, S. Lidin, I. Persson, M. Sandstrom, Chem. Eur. J. 2005, 11, 4065-4077;
196. (d) K. Egashira, Y. Yoshimura, H. Kanno, Y. Suzuki, J. Therm. Anal. Calorim. 2003, 71, 501-508;
197. e) H. Zineddine, M. Hnach, M. Hamidi, J. Fluorine Chem. 1998, 88, 139-141;
198. f) M. Nakayama, S. Nakamura, N. Yanagihara, Polyhedron 1998, 17, 3625-3631.
199. P. Bonhôte, A.-P. Dias, N. Papageorgiou, M. Kalyansundaram, K. Grätzel, Inorg. Chem. 1996, 35, 1168-1178.
200. SigmaPlot 2000 version. 6.0., SPSS Inc, Chicago, IL, 2000.