Lanthanide-Catalyst-Mediated Tandem Double Intramolecular Hydroalkoxylation/Cyclization of Dialkynyl Dialcohols: Scope and Mechanism

Chemistry - A European Journal

Volumn 16, Issue 17, 2010, Pages 5148-5162

  Seo, Sungyong ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Heterogeneous catalysis; Hydroalkoxylation; Lanthanides; Oxygen heterocycles; Parallel reactions

Indexed keywords

HETEROGENEOUS CATALYSIS; HYDROALKOXYLATION; LANTHANIDES; OXYGEN HETEROCYCLES; PARALLEL REACTIONS;

CATALYSIS; CATALYSTS; ETHERS; ISOTOPES; OXYGEN; RARE EARTH ELEMENTS; TRANSITION METALS;

CYCLIZATION;

ALCOHOL DERIVATIVE; ALKYNE; BENZOFURAN DERIVATIVE; LANTHANIDE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALCOHOLS; ALKYNES; BENZOFURANS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; LANTHANOID SERIES ELEMENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 77951557943     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903027     Document Type: Article

References (180)

1. a) R. H. Bates, M. Chen, W. R. Roush, Curr. Opin. Drug Discov. Devel. 2008, 11, 778 -792;
2. b) K. S. M. Salih, M. T. Ayoub, H. A. Saadeh, N. A. Al-Masoudi, M. S. Mubarak, Heterocycles 2007, 71, 1577-1587;
3. c) Y. Kashman, A. Rudi, D. Pappo, Pure Appl. Chem. 2007, 79, 491 -505;
4. d) M. C. Elliott, E. Williams, J. Chem. Soc. Perkin Trans. 1 2001, 2303-2340;
5. e) A. Mitchenson, A. Nadin, J. Chem. Soc. Perkin Trans. 1 2000, 2862 -2892;
6. f) M. C. Elliott, J. Chem. Soc. Perkin Trans. 1 2002, 2301-2323;
7. g) A. J. Sargent, T. M. Cresp in Comprehensive Organic Chemistry, Vol.4 (Ed.: P. G. Sammes), Pergamon, Oxford, 1979, pp. 693-744;
8. h) A. R. Katritzky, A. F. Pozharskii, Handbook of Heterocyclic Chemistry, 2nd ed., Pergamon, Oxford, 2000.
9. a) Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073;
10. b) E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842;
11. c) R. C. Larcock, W. W. Leong in Comprehensive Organic Synthesis, Vol.4 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991;
12. d) C. W. Bird, G. W. H. Cheeseman in Comprehensive Heterocyclic Chemistry, Vol.4 (Eds.: A. R. Katrinsky, C. W. Rees), Pergamon, Oxford, 1984, pp. 89-154.
13. a) B. M. Trost, A. C. Gutierrez, R. C. Livingston, Org. Lett. 2009, 11, 2539-2542;
14. b) F. E. McDonald, K. S. Reddy, Y. Díaz, J. Am. Chem. Soc. 2000, 122, 4304-4309;
15. c) F. E. McDonald, Chem. Eur. J. 1999, 5, 3103-3106;
16. d) B. M. Trost, Y. H. Rhee, J. Am. Chem. Soc. 1999, 121, 11680-11683;
17. e) P. Compain, J. Goré, J.-M. Vatèle, Tetrahedron 1996, 52, 10405-10416;
18. f) P. Compain, J. Goré, J.-M. Vatèle, Tetrahedron Lett. 1995, 36, 4059-4062.
19. a) T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992;
20. b) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137 -170;
21. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163;
22. c) P. A. Wender, B. L. Miller in Organic Synthesis Theory and Applications, Vol.2 (Ed.: T. Hudlicky), JAI Press, Greenwich, 1993.
23. For reviews on atom-economical processes, see: a) C.-J. Li, B. M. Trost, Proc. Natl. Acad. Sci. USA 2008, 105, 13197-13202;
24. b) C. J. Li, Chem. Rev. 2005, 105, 3095-3166;
25. c) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705;
26. d) P. N. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694;
27. e) B. M. Trost, D. F. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067-2096;
28. f) B. M. Trost, M. J. Krische, Synlett 1998, 1-16;
29. g) B. M. Trost, Science 1991, 254, 1471-1477.
30. For reviews of tandem reactions, see: a) K. Hiratani, M. Albrecht, Chem. Soc. Rev. 2008, 37, 2413-2421;
31. b) C. J. Chapman, C. G. Frost, Synthesis 2007, 1-21;
32. c) L. F. Tietze, F. Haunert, Stimulating Concepts in Chemistry (Eds.: F. Vögtle, J. F. Stoddart, M. Shibasaki), Wiley-VCH, Weinheim, 2000, pp. 39 -64;
33. d) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959-5989;
34. e) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
35. f) S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137-165;
36. g) J. D. Winkler, Chem. Rev. 1996, 96, 167-176.
37. a) F. Alonso, I. P. Beletsaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159;
38. b) M. A. Tius in Modern Allene Chemistry, Vol.2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, pp. 834-838;
39. c) K. Tani, Y. Kataoka in Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, pp. 171-216;
40. d) P. A. Bartlett in Asymmetric Synthesis, Vol.3 (Ed.: J. D. Morrisson), Academic Press, New York, 1984, p. 455.
41. For examples of alkene hydroalkoxylation, see: a) A. Dzudza, T. J. Marks, Chem. Eur. J. 2010, 16, 3403-3422;
42. b) B. D. Kelly, J. M. Allen, R. E. Tundel, T. H. Lambert, Org. Lett. 2009, 11, 1381-1383;
43. c) A. R. Chianese, S. J. Lee, M. R. Gagné, Angew. Chem. 2007, 119, 4118-4136;
44. Angew. Chem. Int. Ed. 2007, 46, 4042-4059;
45. d) L. Coulombel, M. Rajzmann, J.-M. Pons, S. Olivero, E. Duñach, Chem. Eur. J. 2006, 12, 6356-6365;
46. e) C.-G. Yang, C. He, J. Am. Chem. Soc. 2005, 127, 6966-6967;
47. f) Y. Oe, T. Ohta, Y. Ito, Synlett 2005, 179-181;
48. g) H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 9536-9537.
49. For examples of alkyne hydroalkoxylation, see: a) S. Bhunia, K.-C. Wang, R.-S. Liu, Angew. Chem. 2008, 120, 5141-5144;
50. Angew. Chem. Int. Ed. 2008, 47, 5063 -5066;
51. b) N. T. Patil, L. M. Lutete, H. Wu, N. K. Pahadi, I. D. Gridnev, Y. Yamamoto, J. Org. Chem. 2006, 71, 4270-4279;
52. c) X. Li, A. R. Chianese, T. Vogel, R. H. Crabtree, Org. Lett. 2005, 7, 5437- 5440;
53. d) P. Wipf, T. H. Graham, J. Org. Chem. 2003, 68, 8798-8807;
54. e) Y. Sheng, D. G. Musaev, K. S. Reddy, F. E. McDonald, K. Morokuma, J. Am. Chem. Soc. 2002, 124, 4149-4157;
55. f) B. M. Trost, Y. H. Rhee, J. Am. Chem. Soc. 2002, 124, 2528-2533;
56. g) I. Kadota, L. M. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210;
57. h) P. Pale, J. Chuche, Eur. J. Org. Chem. 2000, 1019 -1025;
58. i) S. Elgafi, L. D. Field, B. A. Messerle, J. Organomet. Chem. 2000, 607, 97-104;
59. j) F. E. McDonald, K. S. Reddy, Y. Díaz, J. Am. Chem. Soc. 2000, 122, 4304-4309;
60. k) F. E. McDonald, Chem. Eur. J. 1999, 5, 3103-3106;
61. l) D. Tzalis, C. Koradin, P. Knochel, Tetrahedron Lett. 1999, 40, 6193-6195;
62. m) S. Cacchi, J. Organomet. Chem. 1999, 576, 42-64.
63. For examples of allene hydroalkoxylation, see: a) R. S. Paton, F. Maseras, Org. Lett. 2009, 11, 2237-2240;
64. b) Z. Zhang, R. A. Widenhoefer, Org. Lett. 2008, 10, 2079-2081;
65. c) Z. Zhang, R. A. Widehoefer, Angew. Chem. 2007, 119, 287-289;
66. Angew. Chem. Int. Ed. 2007, 46, 283-285;
67. d) S. Ma, Chem. Rev. 2005, 105, 2829-2871;
68. e) R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12 -21;
69. f) C. Mukai, H. Yamashita, M. Hanaoka, Org. Lett. 2001, 3, 3385-3387.
70. A. Diéguez-Vázquez, C. C. Tzschucke, J. Crecente-Campo, S. McGrath, S. V. Ley, Eur. J. Org. Chem. 2009, 1698-1706.
71. V. Belting, N. Krause, Org. Lett. 2006, 8, 4489-4492.
72. E. Genin, S. Antoniotti, V. Michelet, J.-P. Genat, Angew. Chem. 2005, 117, 5029-5033;
73. Angew. Chem. Int. Ed. 2005, 44, 4949-4953.
74. Y. Zhang, J. Xue, Z. Xin, Z. Xie, Y. Li, Synlett 2008, 940-944.
75. B. A. Messerle, K. Q. Vuong, Organometallics 2007, 26, 3031-3040.
76. B. A. Messerle, K. Q. Vuong, Pure Appl. Chem. 2006, 78, 385-390.
77. A. Diíguez-Vázquez, C. C. Tzschucke, W. Y. Lam, S. V. Ley, Angew. Chem. 2008, 120, 216 -219;
78. Angew. Chem. Int. Ed. 2008, 47, 209-212.
79. B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907-4910.
80. a) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673 -686;
81. b) X. Yu, T. J. Marks, Organometallics 2007, 26, 365 -376;
82. c) J.-S. Ryu, T. J. Marks, F. E. McDonald, J. Org. Chem. 2004, 69, 1038-1052;
83. d) S. Hong, A. M. Kawaoka, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 15878-15892;
84. e) J.-S. Ryu, T. J. Marks, F. E. McDonald, Org. Lett. 2001, 3, 3091-3094;
85. f) V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 121, 3633 - 3639;
86. g) V. M. Arredondo, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 4871-4872;
87. h) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 1757-1771;
88. i) P. W. Roesky, C. L. Stern, T. J. Marks, Organometallics 1997, 16, 4705 -4711;
89. j) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295 -9306;
90. k) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 707-708;
91. l) C. M. Haar, C. L. Stern, T. J. Marks, Organometallics 1996, 15, 1765;
92. m) M. A. Giardello, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241-10254;
93. n) M. A. Giardello, V. P. Conticello, L. Brard, M. Sabat, A. L. Rheingold, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10212 - 10240;
94. o) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275-294.
95. a) A. Motta, I. L. Fragala, T. J. Marks, Organometallics 2005, 24, 4995-5003;
96. b) A. M. Kawaoka, M. R. Douglass, T. J. Marks, Organometallics 2003, 22, 4630-4632;
97. c) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283-292;
98. d) M. R. Douglass, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 2001, 123, 10221-10238.
99. For recent organolanthanide reviews, see: a) S. B. Amin, T. J. Marks, Angew. Chem. 2008, 120, 2034-2054;
100. Angew. Chem. Int. Ed. 2008, 47, 2006-2025;
101. b) H. C. Aspinall, Chem. Rev. 2002, 102, 1807-1850;
102. c) F. T. Edelmann, D. M. M. Freckmann, H. Schumann, Chem. Rev. 2002, 102, 1851-1896;
103. d) S. Arndt, J. Okuda, Chem. Rev. 2002, 102, 1953-1976;
104. e) G. A. Molander, A. C. Romero, Chem. Rev. 2002, 102, 2161-2186;
105. f) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2210;
106. g) J. Inanaga, H. Furuno, T. Hayano, Chem. Rev. 2002, 102, 2211-2226;
107. h) G. A. Molander, Chemtracts: Org. Chem. 1998, 18, 237-263;
108. i) F. T. Edelmann, Top. Curr. Chem. 1996, 179, 247-276;
109. j) F. T. Edelmann in Comprehensive Organometallic Chemistry, Vol.4 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1995, Chapter 2;
110. k) H. Schumann, J. A. Meese-Marktscheffel, L. Esser, Chem. Rev. 1995, 95, 865-986;
111. l) T. J. Marks, R. D. Ernst in Comprehensive Organometallic Chemistry (Eds.: G. Wilkinson, F. G. A. Stone, E.W. Abel), Pergamon, Oxford, 1982, Chapter 21.
112. a) S. A. Schuetz, V. W. Day, R. D. Sommer, A. L. Rheingold, J. A. Belot, Inorg. Chem. 2001, 40, 5292 -5295;
113. b) D. C. Bradley, J. S. Ghotra, F. A. Hart, J. Chem. Soc. Dalton Trans. 1973, 1021-1023;
114. c) E. C. Alyea, D. C. Bradley, R. G. Copperthwaite, J. Chem. Soc. Dalton Trans. 1972, 1580-1584.
115. Q. Shen, W. Huang, J. Wang, X. Zhou, Organometallics 2008, 27, 301-303.
116. L. Zhang, S. Wang, E. Sheng, S. Zhou, Green Chem. 2005, 7, 683-686.
117. a) K. Komeyama, D. Sasayama, T. Kawabata, K. Takehira, K. Takaki, Chem. Commun. 2005, 634-636;
118. b) K. Komeyama, D. Sasayama, T. Kawabata, K. Takehira, K. Takaki, J. Org. Chem. 2005, 70, 10679-10687.
119. a) K. Komeyama, T. Kawabata, K. Takehira, K. Takaki, J. Org. Chem. 2005, 70, 7260-7266;
120. b) M. Nishiura, Z. Hou, Y. Wakatsuki, T. Yamaki, T. Miyamoto, J. Am. Chem. Soc. 2003, 125, 1184-1185;
121. c) M. Nishiura, Z. Hou, J. Mol. Catal. A 2004, 213, 101-106.
122. Q. H. Li, S. W. Wang, S. L. Zhou, G. S. Yang, X. C. Zhu, Y. Y. Liu, J. Org. Chem. 2007, 72, 6763-6767.
123. a) Y. Horino, T. Livinghouse, Organometallics 2004, 23, 12-14;
124. b) T. Gountchev, T. D. Tilley, Organometallics 1999, 18, 5661-5667.
125. Y. Horino, T. Livinghouse, M. Stan, Synlett 2004, 2639-2641.
126. a) Y. H. Chen, Z. Y. Zhu, J. Zhang, J. Z. Shen, X. G. Zhou, J. Organomet. Chem. 2005, 690, 3783-3789;
127. b) M. R. Bürgstein, H. Berberich, P. W. Roesky, Chem. Eur. J. 2001, 7, 3078-3085;
128. c) H. Berberich, P. W. Roesky, Angew. Chem. 1998, 110, 1618-1620;
129. Angew. Chem. Int. Ed. 1998, 37, 1569-1571.
130. S. Seo, T. J. Marks, Org. Lett. 2008, 10, 317-319.
131. a) A. Motta, I. L. Fragala, T. J. Marks, Organometallics 2006, 25, 5533-5539;
132. b) A. Motta, G. Lanza, I. L. Fragala, T. J. Marks, Organometallics 2004, 23, 4097-4104;
133. c) J. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12584-12605;
134. d) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933-2935.
135. a) A. Motta, I. L. Fragala, T. J. Marks, unpublished results;
136. b) S. Seo, X. Yu, T. J. Marks, J. Am. Chem. Soc. 2009, 131, 263-276;
137. c) X. Yu, S. Seo, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 7244-7245.
138. a) S. P. Nolan, D. Stern, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 7844-7853;
139. b) D. F. McMillen, D. M. Golden, Annu. Rev. Phys. Chem. 1982, 33, 493-532;
140. c) S. W. Benson, Thermochemical Kinetics, 2nd ed., Wiley, New York, 1976, Appendix Tables A10, 11 and 22;
141. 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. MartinhoSimoes), Kluwer, Amsterdam, 1992, pp. 35-54;
142. 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), Plenum, New York, 1990, pp. 113-125;
143. f) T. J. Marks in Bonding Energetics in Organometallic Compounds (Ed.: T. J. Marks), ACS, Washington, 1990, pp. 1-18;
144. g) S. P. Nolan, D. Stern, D. Hedden, T. J. Marks in Bonding Energetics in Organometallic Compounds (Ed.: T. J. Marks), ACS, Washington, 1990, pp. 159-174.
145. a) "The Total Synthesis of Spiroketal-Containing Products": V. Vaillancourt, N. E. Pratt, F. Perron, K. F. Albizati in The Total Synthesis of Natural Products, Vol.8, 1st ed. (Ed.: J. A. Simon), Wiley-Interscience, New York, 1992, pp. 533-691;
146. b) F. Perron, K. F. Albizati, Chem. Rev. 1989, 89, 1617-1661.
147. Y. Morimoto, T. Okita, H. Kambara, Angew. Chem. 2009, 121, 2576-2579;
148. Angew. Chem. Int. Ed. 2009, 48, 2538-2541.
149. A. R. Van Dyke, T. F. Jamison, Angew. Chem. 2009, 121, 4494-4496;
150. Angew. Chem. Int. Ed. 2009, 48, 4430-4432.
151. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.
152. H. H. Fox, M. O. Wolf, R. O'Dell, B. L. Lin, R. R. Schrock, M. S. Wrighton, J. Am. Chem. Soc. 1994, 116, 2827-2843.
153. a) S. H. Liu, Y. Chen, K. L. Wan, T. B. Wen, Z. Zhou, M. F. Lo, I. D. Williams, G. Jia, Organometallics 2002, 21, 4984 -4992;
154. b) P. Quayle, S. Rahman, J. Herbert, Tetrahedron Lett. 1995, 36, 8087-8088.
155. J. L. D. De La Cruz, U. Hahn, J.-F. Nierengarten, Tetrahedron Lett. 2006, 47, 3715-3718.
156. J. K. Sorensen, M. Vestergaard, A. Kadziola, K. Kils, M. B. Nielsen, Org. Lett. 2006, 8, 1173-1176.
157. SigmaPlot 2002, version 8.0., SPSS Inc, Chicago, 2002.
158. See the Supporting Information.
159. G. Gaefke, V. Enkelmann, S. Hoeger, Synthesis 2006, 2971-2973.
160. a) Y. Yamanoi, H. Nishihara, J. Org. Chem. 2008, 73, 6671-6678;
161. b) H. K. Christian-Pandya, Z. I. Niazimbetova, F. L. Beyer, M. E. Galvin, Chem. Mater. 2007, 19, 993-1001.
162. a) A. Wu, A. Chakraborty, D. Witt, J. Lagona, F. Damkaci, M. A. Ofori, J. K. Chiles, J. C. Fettinger, L. Isaacs, J. Org. Chem. 2002, 67, 5817-5830;
163. b) Y. H. Lai, A. H. T. Yap, J. Chem. Soc. Perkin Trans. 2 1993, 1373-1377.
164. G. Jeske, L. E. Schock, H. Mauermann, P. N. Swepston, H. Schumann, T. J. Marks, J. Am. Chem. Soc. 1985, 107, 8103-8110.
165. III, 0.977 Å. See: R. D. Shannon, Acta Crystallogr. Sect. A 1976, 32, 751-767.
166. Organolanthanide-catalyzed hydrophosphinations exhibit similar but more pronounced kinetic inhibition effects, depending upon the steric bulk of the product. See: M. R. Douglass, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 2001, 123, 10221-10238.
167. J. I. Steinfeld, J. S. Francisco, W. L. Hase, Chemical Kinetics and Dynamics 2nd ed., Prentice Hall, New Jersey, 1999; pp. 1-13.
168. a) P. J. Robinson, J. Chem. Educ. 1978, 55, 509 - 510;
169. b) S. W. Benson, Thermochemical Kinetics, 2nd ed., Wiley, New York, 1986; pp. 8-10.
170. Parameters in parentheses represent 3σ values derived from the least-squares fit.
171. 3+-arene complexes, see: a) M. N. Bochkarev, Chem. Rev. 2002, 102, 2089-2117;
172. b) H. Liang, Q. Shen, J. Guan, Y. Lin, J. Organomet. Chem. 1994, 474, 113-116;
173. c) G. B. Deacon, Aust. J. Chem. 1990, 43, 1245-1257;
174. d) B. Fan, Q. Shen, Y. Lin, J. Organomet. Chem. 1989, 376, 61-66;
175. e) B. Fan, Q. Shen, Y. Lin, J. Organomet. Chem. 1989, 377, 51-58;
176. f) A. Cotton, W. Schwotzer, Organometallics 1987, 6, 1275-1279;
177. g) A. Cotton, W. Schwotzer, J. Am. Chem. Soc. 1986, 108, 4657-14568
178. a) R. C. Mehrotra, A. Singh, U. M. Tripathi, Chem. Rev. 1991, 91, 1287-1303;
179. b) H. Sheng, F. Xu, Y. Yao, Y. Zhang, Q. Shen, Inorg. Chem. 2007, 46, 7722-7724.
180. E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, 2006, pp. 428-431.