Iminophosphorane-phosphines: Versatile ligands for homogeneous catalysis

Journal of Organometallic Chemistry

Volumn 751, Issue , 2014, Pages 792-808

  García Álvarez, Joaquín ^a   García Garrido, Sergio E ^a   Cadierno, Victorio ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Functionalized phosphines; Hemilabile ligands; Homogeneous catalysis; Iminophosphoranes; Polydentate ligands

Indexed keywords

CATALYSIS; COORDINATION REACTIONS; HYDROGENATION; NITROGEN; PHOSPHORUS COMPOUNDS; TRANSITION METALS;

FUNCTIONALIZED PHOSPHINE; HEMILABILE LIGAND; HOMOGENEOUS CATALYSIS; IMINOPHOSPHORANES; POLYDENTATE LIGAND;

LIGANDS;

EID: 84893458034     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2013.07.009     Document Type: Article

References (172)

1. H. Staudinger, J. Meyer, Helv. Chim. Acta 2 (1919) 635-646.
2. A.W. Johnson, Ylides and Imines of Phosphorus, Wiley-Interscience, New York, 1993.
3. See, for example: (a) P.M. Fresneda, P. Molina, Synlett (2004) 1-17
4. S. Eguchi, ARKIVOC 2 (2005) 98-119
5. F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, J.M. de los Santos, Tetrahedron 63 (2006) 523-575
6. M.-W. Ding, G.-F. Yang, Trends Heterocycl. Chem. 11 (2006) 87-94;
7. G. Hajos, I. Nagy, Curr. Org. Chem. 12 (2008) 39-58
8. F. Palacios, D. Aparicio, G. Rubiales, C. Alonso, J.M. de los Santos, Curr. Org. Chem. 13 (2009) 810-828
9. F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, J.M. de los Santos, in: S. Brase, K. Banert (Eds.), Organic Azides, John Wiley & Sons, Chichester, 2010, pp. 439- 467
10. Q.-Y. Ren, X.-S. Tan, H.-W. He, Curr. Org. Synth. 8 (2011) 752-763
11. P.Molina, A. Tárraga, M. Alfonso, Eur. J. Org. Chem. (2011) 4505-4518.
12. (a) See, for example: (a) I.S. Resck, Quim. Nova 17 (1994) 317-322
13. P. Ilankumaran, G. Zhang, J.G. Verkade, Heteroatom Chem. 11 (2000) 251- 253
14. T. Ishikawa (Ed.), Superbases for Organic Synthesis, John Wiley & Sons, Chichester, 2009.
15. (a) See, for example: (a) H.R. Allcock, Chemistry and Applications of Polyphosphazenes, John Wiley & Sons, New York, 2003
16. M. Gleria, R. de Jaeger (Eds.), Applicative Aspects of Poly(- Organophosphazenes), Nova Science Publishers, New York, 2004
17. M. Gleria, R. de Jaeger (Eds.), Synthesis and Characterization of Poly(- Organophosphazenes), Nova Science Publishers, New York, 2004
18. T. Baumgartner, R. Réau, Chem. Rev. 106 (2006) 4681-4727
19. A.K. Andrianov (Ed.), Polyphosphazenes for Biomedical Applications, John Wiley & Sons, New York, 2009
20. V. Blackstone, A.J. Lough, M. Murray, I. Manners, J. Am. Chem. Soc. 131 (2009) 3658-3667.
21. For reviews on the Staudinger reaction, see: (a) Y.G. Gololobov, I.N. Zhmurova, L.F. Kasukhin, Tetrahedron 37 (1981) 437-472
22. Y.G. Gololobov, L.F. Kasukhin, Tetrahedron 48 (1992) 1353-1406
23. S.S. van Berkel, M.B. van Eldijk, J.C.M. van Hest, Angew. Chem. Int. Ed. 50 (2011) 8806-8827.
24. A.V. Kirsanov, Isv. Akad. Nauk. SSSR, Ser. Khim. (1950) 426-437.
25. Representative examples of this reaction can be found in: (a) T. Rodima, V. Mäemets, I. Koppel, J. Chem. Soc. Perkin Trans. 1 (2000) 2637-2644
26. I. Kaljurand, T. Rodima, A. Pihl, V. Mäemets, I. Leito, I.A. Koppel, M. Mishima, J. Org. Chem. 68 (2003) 9988-9993
27. M. Demange, L. Boubekeur, A. Auffrant, N. Mézailles, L. Ricard, X. Le Goff, P. Le Floch, New J. Chem. 30 (2006) 1745-1754
28. T. Saplinova, C. Lehnert, U. Boehme, J. Wagler, E. Kroke, New J. Chem. 34 (2010) 1893-1908.
29. (a) See, for example: (a) E.W. Abel, S.A. Mucklejohn, Phosphorus Sulfur Relat. Elem. 9 (1981) 235-266 and references cited therein
30. J. Vicente, A. Arcas, D. Bautista, M.C. Ramírez de Arellano, Organometallics 17 (1998) 4544-4550 and references cited therein
31. A. Steiner, S. Zacchini, P.I. Richards, Coord. Chem. Rev. 227 (2002) 193-216.
32. M. Fukui, K. Itoh, Y. Ishii, Bull. Chem. Soc. Jpn. 48 (1975) 2044-2046.
33. See, for example: (a) L. Beaufort, F. Benvenuti, L. Delaude, A.F. Noels, J. Mol. Catal. A: Chem. 283 (2008) 77-82
34. O. Alhomaidan, G. Bai, D.W. Stephan, Organometallics 27 (2008) 6343-6352
35. E. Martinez-Arripe, F. Jean-Baptiste-dit-Dominique, A. Auffrant, X.-F. Le Goff, J. Thuilliez, F. Nief, Organometallics 31 (2012) 4854-4861
36. P.P.M. Hoang, C. Baar, V. Ker, B.M. Shaw, P. Lam, L.D. Henderson, C.A.G. Carter, Y. Jiang, PCT Int. Appl. (2012) WO2012167348
37. P.P.M. Hoang, C. Baar, P.S. Chisholm, D. Rajesh, PCT Int. Appl. (2013) WO2013026131.
38. See, for example: (a) A. Buchard, R.H. Platel, A. Auffrant, X.F. Le Goff, P. Le Floch, C.K. Williams, Organometallics 29 (2010) 2892-2900
39. Z.-A. Ma, Z.-X. Wang, Organometallics 30 (2011) 4364-4373
40. T.-P.-A. Cao, A. Buchard, X.F. Le Goff, A. Auffrant, C.K. Williams, Inorg. Chem. 51 (2012) 2157-2169
41. C. Bakewell, T.-P.-A. Cao, N. Long, X.F. Le Goff, A. Auffrant, C.K. Williams, J. Am. Chem. Soc. 134 (2012) 20577-20580
42. C.A. Wheaton, P.G. Hayes, Catal. Sci. Technol. 2 (2012) 125-138
43. C. Bakewell, T.-P.-A. Cao, X.F. Le Goff, N. Long, A. Auffrant, C.K. Williams, Organometallics 32 (2013) 1475-1483.
44. (a) J. García-Álvarez, J. Díez, J. Gimeno, Green Chem. 12 (2010) 2127-2130
45. J. García-Álvarez, J. Díez, C. Vidal, Green Chem. 14 (2012) 3190-3196
46. J. García-Álvarez, J. Díez, J. Gimeno, F.J. Suárez, C. Vicent, Eur. J. Inorg. Chem. (2012) 5854-5863
47. J.García-Álvarez, J. Díez, C.Vidal, C.Vicent, Inorg.Chem. 52 (2013) 6533-6542.
48. For reviews on hemilabile ligands, see: (a) C.S. Slone, D.A. Weinberger, C.A. Mirkin, Prog. Inorg. Chem. 48 (1999) 233-350
49. P. Braunstein, F. Naud, Angew. Chem. Int. Ed. 40 (2001) 680-699;
50. (c) A.D. Burrows, Sci. Prog. 85 (2002) 199-217
51. P. Braunstein, J. Organomet. Chem. 689 (2004) 3953-3967
52. S.E. Angell, C.W. Rogers, Y. Zhang, M.O. Wolf, W.E. Jones, Coord. Chem. Rev. 250 (2006) 1829-1841
53. M. Bassetti, Eur. J. Inorg. Chem. (2006) 4473-4482
54. F.Y. Kwong, A.S.C. Chan, Synlett (2008) 1440-1448
55. S. Gu, C. Chen, H. Qiu, W. Chen, Curr. Org. Chem. 15 (2011) 3291-3308
56. J.I. van der Vlugt, Eur. J. Inorg. Chem. (2012) 363-375.
57. For overviews on the coordination chemistry of iminophosphoraneephosphines of type R2P-X-P(dbndN0R)R2 (X = alkyl or aryl chain), see: (a) K.V. Katti, R.G. Cavell, Comments Inorg. Chem. 10 (1990) 53-73
58. R.G. Cavell, Curr. Sci. 78 (2000) 440-451.
59. Selected iminophosphorane-based catalysts, including examples with iminophosphoraneephosphine ligands, have been recently highlighted in: Auffrant L'Actualité Chim. 359 (2012) 13-19.
60. The chemistry of rutheniumcomplexeswith iminophosphorane ligands has been reviewed: V. Cadierno, J. García-Álvarez, in: D.B. Watson (Ed.), Ruthenium: Properties, Production and Applications, Nova Science Publishers, New York, 2011.
61. See, for example: (a) P.A. Chaloner, M.A. Esteruelas, F. Joó, L.A. Oro, Homogeneous Hydrogenation, Kluwer Academic Publishers, Dordrecht, 1994
62. J.G. de Vries, C.J. Elsevier (Eds.), Handbook of Homogeneous Hydrogenation, Willey-VCH, Weinheim, 2007.
63. (a) D.J. Law, R.G. Cavell, J. Mol. Catal. 91 (1994) 175-186
64. R.G. Cavell, D.J. Law, R.W.Reed, US Pat. Appl. (1994) US887014.
65. R. Venkateswaran, M.S. Balakrishna, S.M. Mobin, Eur. J. Inorg. Chem. (2007) 1930-1938.
66. F. Lorenzini, K.T. Hindle, S.J. Craythorne, A.R. Crozier, F. Marchetti, C.J. Martin, P.C. Marr, A.C. Marr, Organometallics 25 (2006) 3912-3919.
67. In general, involvement of chiral iminophosphoranes in asymmetric catalysis remains almost unexplored: (a) M.T. Reetz, E. Bohres, R. Goddard, Chem. Commun. (1998) 935-936
68. M. Sauthier, J. Forniés-Cámer, L. Toupet, R. Réau, Organometallics 19 (2000) 553-562.
69. Unexploited examples in catalysis of transitionemetal complexes with optically active iminophosphoraneephosphine ligands can be found in: L. Boubekeur, L. Ricard, N. Mézailles, M. Demange, A. Auffrant, P. Le Floch Organometallics 25 (2006) 3091-3094.
70. (a) T.T. Co, S.C. Shim, C.S. Cho, T.-J. Kim, S.O. Kang, W.-S. Han, J. Ko, C.-K. Kim, Organometallics 24 (2005) 4824-4831
71. T.T. Co, T.-J. Kim, Chem. Commun. (2006) 3537-3539
72. T.-J. Kim, Y.M. Chang, G.H. Lee, I.K. Kang, T.T. Co, Repub. Korean Kongkae Taeho Kongbo (2007). KR2007013905.
73. See, for example: (a) R.H. Morris, Chem. Soc. Rev. 38 (2009) 2282-2291 and references cited therein
74. S. Fleisher, S. Zhou, K. Junge, M. Beller, Angew. Chem. Int. Ed. 52 (2013) 5120-5124 and references cited therein.
75. A. Buchard, H. Heuclin, A. Auffrant, X.F. Le Goff, P. Le Floch, Dalton Trans. (2009) 1659-1667.
76. See, for example: (a) G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev. 92 (1992) 1051-1069
77. S. Gladiali, E. Alberico, Chem. Soc. Rev. 35 (2006) 226-236
78. J.S.M. Samec, J.-E. Bäckvall, P.G. Andersson, P. Brandt, Chem. Soc. Rev. 35 (2006) 237-248
79. S. Gladiali, R. Taras, in: P.G. Andersson, I.J. Munslow (Eds.), Modern Reduction Methods, Wiley-VCH, Weinheim, 2008, pp. 135-158
80. M. Wills, in: P.G. Andersson, I.J. Munslow (Eds.), Modern Reduction Methods, Wiley-VCH, Weinheim, 2008, pp. 271-296.
81. A. Buchard, E. Payet, A. Auffrant, X. Le Goff, P. Le Floch, New J. Chem. 34 (2010) 2943-2949.
82. V. Cadierno, P. Crochet, J. García-Álvarez, S.E. García-Garrido, J. Gimeno, J. Organomet. Chem. 663 (2002) 32-39.
83. (a) V. Cadierno, J. Díez, S.E. García-Garrido, S. García-Granda, J. Gimeno, J. Chem. Soc. Dalton Trans. (2002) 1465-1472
84. V. Cadierno, J. Díez, J. García-Álvarez, J. Gimeno, Chem. Commun. (2004) 1820-1821.
85. (a) V. Cadierno, P. Crochet, J. Díez, J. García- Álvarez, S.E. García-Garrido, J. Gimeno, S. García-Granda, M.A. Rodríguez, Inorg. Chem. 42 (2003) 3293- 3307
86. V. Cadierno, P. Crochet, J. Díez, J. García-Álvarez, S.E. García-Garrido, S. García-Granda, J. Gimeno, M.A. Rodríguez, Dalton Trans. (2003) 3240-3249.
87. A. Picot, H. Dyer, A. Buchard, A. Auffrant, L. Vendier, P. Le Floch, S. Sabo-Etienne, Inorg. Chem. 49 (2010) 1310-1312.
88. L. Boubekeur, S. Ulmer, L. Ricard, N. Mézailles, P. Le Floch, Organometallics 25 (2006) 315-317.
89. H. Dyer, A. Picot, L. Vendier, A. Auffrant, P. Le Floch, S. Sabo-Etienne, Organometallics 30 (2011) 1478-1486.
90. See, for example: (a) N. Miyaura (Ed.), Cross-coupling Reactions: a Practical Guide, Springer, Berlin, 2002
91. A. de Meijere, F. Diederich (Eds.), Metal-catalyzed Cross-coupling Reactions, second ed., Wiley-VCH, Weinheim, 2004
92. Y. Nishihara (Ed.), Applied Cross-coupling Reactions, Springer, Berlin, 2013.
93. (a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16 (1975) 4467- 4470
94. K. Sonogashira, J. Organomet. Chem. 653 (2002) 46-49
95. R. Chinchilla, C. Nájera, Chem. Rev. 107 (2007) 874-922
96. R. Chinchilla, C. Nájera, Chem. Soc. Rev. 40 (2011) 5048-5121.
97. A. Arques, D. Auñon, P. Molina, Tetrahedron Lett. 45 (2004) 4337-4340.
98. P. Molina, A. Arques, A. García, M.C. Ramírez de Arellano, Tetrahedron Lett. 38 (1997) 7613-7616.
99. (a) N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 20 (1979) 3437-3440
100. N. Miyaura, A. Suzuki, Chem. Commun. (1979) 866-867
101. N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457-2483
102. A. Suzuki, J. Organomet. Chem. 576 (1999) 147-168
103. A. Suzuki, Chem. Commun. (2005) 4759-4763
104. F. Alonso, I.P. Beletskaya, M. Yus, Tetrahedron 64 (2008) 3047-3101
105. R. Narayanan, Molecules 15 (2010) 2124-2138.
106. A. Buchard, B. Komly, A. Auffrant, X.F. Le Goff, P. Le Floch, Organometallics 27 (2008) 4380-4385.
107. D.G. Hall (Ed.), Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, second ed., Wiley-VCH, Weinheim, 2011.
108. (a) K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 94 (1972) 4374- 4376
109. R.J.P. Corriu, J.P. Masse, J. Chem. Soc. Chem. Commun. (1972) 144;
110. (c) K. Tamao, J. Organomet. Chem. 653 (2002) 23-26
111. J. Adrio, J.C. Carretero, Chem. Catal. Chem. 2 (2010) 1384-1386
112. M.M. Heravi, P. Hajiabbasi, Monatsh. Chem. 143 (2012) 1575-1592.
113. Z.-X. Wang, L. Wang, Chem. Commun. (2007) 2423-2425.
114. K. Sun, L. Wang, Z.-X. Wang, Organometallics 27 (2008) 5649-5656.
115. C. Zhang, Z.-X. Wang, Organometallics 28 (2009) 6507-6514.
116. (a) A.O. King, N. Okukado, E. Negishi, J. Chem. Soc. Chem. Commun. (1977) 683-684
117. E. Negishi, A.O. King, N. Okukado, J. Org. Chem. 42 (1977) 1821-1823
118. P. Knochel, R.D. Singer, Chem. Rev. 93 (1993) 2117-2188
119. V.P. Phapale, D.J. Cárdenas, Chem. Soc. Rev. 38 (2009) 1598-1607
120. C. Valente, M.E. Belowich, N. Hadei, M.G. Organ, Eur. J. Org. Chem. (2010) 4343-4354
121. L. Jin, A. Lei, Org. Biomol. Chem. 10 (2012) 6817-6825.
122. See, for example: (a) J. Skupinska, Chem. Rev. 91 (1991) 613-648
123. J.T. Dixon, M.J. Green, F.M. Hess, D.H. Morgan, J. Organomet. Chem. 689 (2004) 3641-3668
124. F. Speiser, P. Braunstein, L. Saussine, Acc. Chem. Res. 38 (2005) 784-793
125. D.F. Wass, Dalton Trans. (2007) 816-819
126. G. Fink, H.-H. Brintzinger, in: G.P. Chiusoli, P.M. Maitlis (Eds.), Metal Catalysis in Industrial Organic Processes, RSC Publishing, Cambridge, 2008, pp. 218-254
127. D.S. McGuinness, Chem. Rev. 111 (2011) 2321-2341.
128. (a) W. Keim, F.H. Kowaldt, R. Goddard, C. Krüger, Angew. Chem. Int. Ed. Engl. 17 (1978) 466-467
129. B. Reuben, H. Wittcoff, J. Chem. Ed. 65 (1988) 605-607
130. P. Kuhn, D. Sémeril, D. Matt, M.J. Chetcuti, P. Lutz, Dalton Trans. (2007) 515-528.
131. In the context of a broad study Cavell and co-workers described the use of several transition metal iminophosphorane-based complexes, including [Ni {k2-(P,N)-Ph2PCH2P(]N-p-C6F4CN)Ph2}2] and [Ni(cod){k2-(P,N)-Ph2PCH2P(] N-p-C6F4CN)Ph2}], for the polymerization of ethylene. Unfortunately, these iminophosphoraneephosphine Ni(0) complexes were no viable catalysts due their poor solubility in conventional organic solvents: (a) A.F. Somogyvari, B.L. Creed, A.P. Nicola, A.R. Sanger, D.J. Law, R.G.Cavell, US Pat. Appl. (1996) US5557023
132. R.G. Cavell, B. Creed, L. Gelmini, D.J. Law, R. McDonald, A.R. Sanger, A. Somogyvari, Inorg. Chem. 37 (1998) 757-763
133. I. McKay, A. Ciupa, A.F. Somogyvari, B.L. Creed, A.R. Sanger, D.J. Law, R.G.Cavell, US Pat. Appl. (2000) US6013745.
134. C. Zhang, W.-H. Sun, Z.-X. Wang, Eur. J. Inorg. Chem. (2006) 4895-4902.
135. (a) A. Buchard, A. Auffrant, C. Klemps, L. Vu-Do, L. Boubekeur, X.F. Le Goff, P. Le Floch, Chem. Commun. (2007) 1502-1504
136. V. Tognetti, A. Buchard, A. Auffrant, I. Ciofini, P. Le Floch, C. Adamo, J. Mol. Model 19 (2013) 2107-2118.
137. See, for example: (a) D. Rechavi, M. Lemaire, Chem. Rev. 102 (2002) 3467- 3494
138. H. Lebel, J.-F. Marcoux, C. Molinaro, A.B. Charette, Chem. Rev. 103 (2003) 977-1050
139. R.A.C. Leao, V.F. Ferreira, S. Pinheiro, Quim. Nova 30 (2007) 1721-1731
140. H. Pellissier, Tetrahedron 64 (2008) 7041-7095.
141. V.D.M. Hoang, P.A.N. Reddy, T.-J. Kim, Tetrahedron Lett. 48 (2007) 8014- 8017.
142. See, for example: (a) X.L. Hou, H.Y. Cheung, T.Y. Hon, P.L. Kwan, T.H. Lo, S.Y. Tong, H.N.C. Wong, Tetrahedron 54 (1998) 1955-2020
143. R.C.D. Brown, Angew. Chem. Int. Ed. 44 (2005) 850-852
144. S.F. Kirsch, Org. Biomol. Chem. 4 (2006) 2076-2080
145. D.M. D'Souza, T.J.J. Müller, Chem. Soc. Rev. 36 (2007) 1095-1108
146. N.T. Patil, Y. Yamamoto, ARKIVOC 10 (2007) 121-141
147. G. Balme, D. Bouyssi, N. Monteiro, Heterocycles 73 (2007) 87-124
148. V. Cadierno, P. Crochet, Curr. Org. Synth. 5 (2008) 343-364
149. L. Hao, Z.-P. Zhan, Curr. Org. Chem. 15 (2011) 1625-1643
150. W.J. Moran, A. Rodríguez, Org. Prep. Proc. Int. 44 (2012) 103-130
151. W. Jia-Jie, Y. Zhu, Z.-P. Zhan, Asian J. Org. Chem. 1 (2012) 108-129.
152. V. Cadierno, J. Díez, J. García-Álvarez, J. Gimeno, N. Nebra, J. Rubio-García, Dalton Trans. (2006) 5593-5604.
153. B. Gabriele, G. Salerno, M. Costa, Synlett (2004) 2468-2483 and references cited therein.
154. See, for example: (a) S. Swaminathan, K.V. Narayanan, Chem. Rev. 71 (1971) 429-438
155. D.A. Engel, G.B. Dudley, Org. Biomol. Chem. 7 (2009) 4149-4158
156. V. Cadierno, P. Crochet, S.E. García-Garrido, J. Gimeno, Dalton Trans. 39 (2010) 4015-4031
157. J. García-Álvarez, S.E. García-Garrido, P. Crochet, V. Cadierno, Curr. Top. Catal. 10 (2012) 35-56.
158. (a) J. García-Álvarez, J. Díez, J. Gimeno, C.M. Seifried, Chem. Commun. 47 (2011) 6470-6472
159. J. García-Álvarez, J. Díez, J. Gimeno, C.M. Seifried, C. Vidal, Inorg. Chem. 52 (2013) 5428-5437.
160. Detailed information regarding ruthenium Lewis acid catalyzed DielseAlder reactions can be found in the following review articles: (a) R.F.R. Jazzar, E.P. Kündig, in: S.-I. Murahashi (Ed.), Ruthenium in Organic Synthesis, Wiley- VCH, Weinheim, 2004, pp. 257-276
161. S. Dérien, F. Monnier, P.H. Dixneuf, Top. Organomet. Chem. 11 (2004) 1- 44
162. J. Faller, J. Parr, Curr. Org. Chem. 10 (2006) 151-163.
163. A.E. Díaz-Álvarez, P. Crochet, M. Zablocka, V. Cadierno, C. Duhayon, J. Gimeno, J.-P. Majoral, New J. Chem. 30 (2006) 1295-1306.
164. (a) M.S. Karasch, G. Sosnovsky, J. Am. Chem. Soc. 80 (1958) 756
165. M.S.Karasch,G. Sosnovsky,N.C. Yang, J.Am. Chem. Soc. 81 (1959) 5819-5824.
166. V.D.M. Hoang, P.A.N. Reddy, T.-J. Kim, Organometallics 27 (2008) 1026-1027.
167. (a) J. Eames, M. Watkinson, Angew. Chem. Int. Ed. 40 (2001) 3567-3571
168. R.M. Camble, G. Sekar, M. Chandrasekhar, V.K. Singh, PINSA-A: Proc. Indian Natl. Sci. Acad. Part A 68 (2002) 423-433
169. M.B. Andrus, J.C. Lashley, Tetrahedron 58 (2002) 845-866
170. I.I. Moiseev, M.N. Vargaftik, Coord. Chem. Rev. 248 (2004) 2381-2391.
171. T.T. Co, S.C. Shim, C.S. Cho, D.-U. Kim, T.-J. Kim, Bull. Korean Chem. Soc. 26 (2005) 1359-1365.
172. R.G. Cavell, K.V. Katti, PCT Int. Appl. (1992) WO92/04118.