d0fN-metal complexes supported by ferrocene-based chelating ligands

Comments on Inorganic Chemistry

Volumn 31, Issue 5, 2010, Pages 196-241

  Diaconescu, Paula L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78649720041     PISSN: 02603594     EISSN: 15489574     Source Type: Journal    
DOI: 10.1080/02603594.2010.534023     Document Type: Review

References (116)

1. Kealy, T. J. and P. L. Pauson. 1951. A new type of organo-iron compound. Nature, 168: 1039-1040.
2. Miller, S. A., J. A. Tebboth, and J. F. Tremaine. 1952. Dicyclopentadienyl iron. J. Chem. Soc., XX: 632-635.
3. Wilkinson, G., M. Rosenblum, M. C. Whiting, and R. B. Woodward. 1952. The structure of iron bis-cyclopentadienyl. J. Am. Chem. Soc., 74(8): 2125-2126.
4. Fischer, E. O. and W. Pfab. 1952. Cyclopentadien-Metallkomplexe, ein neuer typ metallorganischer Verbindungen. Z. Naturforsch. B, 7: 377-379.
5. Eiland, P. F. and R. Pepinsky. 1952. X-ray examination of iron biscyclopentadienyl. J. Am. Chem. Soc., 1952, 74(19): 4971-4971.
6. Nobel Foundation. 1973. The 1973 Nobel Prize in Chemistry. http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/press.html
7. Štěpnička, P. 2008. Ferrocenes: Ligands, Materials and Biomolecules, West Sussex, UK: Wiley.
8. Togni, A. and T. Hayashi. 1995. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science, Weinheim, Germany: VCH Publishers.
9. Connelly, N. G. and W. E. Geiger. 1996. Chemical redox agents for organometallic chemistry. Chem. Rev., 96(2): 877-910.
10. Stubbe, J. and W. A. van der Donk. 1998. Protein radicals in enzyme catalysis. Chem. Rev., 98(2): 705-762.
11. Jazdzewski, B. A. and W. B. Tolman. 2000. Understanding the copper-phenoxyl radical array in galactose oxidase: contributions from synthetic modeling studies. Coord. Chem. Rev., 200-202: 633-685.
12. Fuhrhop, J. H. 1974. The reactivity of the porphyrin ligand. Angew. Chem. Int. Ed., 13(5): 321-335.
13. Chaudhuri, P. and K. Wieghardt. 2001. Phenoxyl radical complexes. Prog. Inorg. Chem., 50: 151-216.
14. Grützmacher, H. 2008. Cooperating ligands in catalysis. Angew. Chem. Int. Ed., 47(10): 1814-1818.
15. Marr, G. and T. Hunt. 1969. Unsymmetrically disubstituted ferrocenes. Part VIII. Synthesis and reactivity of some 2-substituted ferrocenylphosphines. J. Chem. Soc. C, 1070-1072.
16. Bishop, J. J., A. Davison, M. L. Katcher, D. W. Lichtenberg, R. E. Merrill, and J. C. Smart. 1971. Symmetrically disubstituted ferrocenes: I. The synthesis of potential bidentate ligands. J. Organomet. Chem., 27(2): 241-249.
17. Gibson, V. C. and S. K. Spitzmesser. 2003. Advances in non-metallocene olefin polymerization catalysis. Chem. Rev., 103(1): 283-315.
18. Piers, W. E. and D. J. H. Emslie. 2002. Non-cyclopentadienyl ancillaries in organogroup 3 metal chemistry: a fine balance in ligand design. Coord. Chem. Rev., 233-234: 131-155.
19. Siemeling, U. and T.-C. Auch. 2005. 1,1'-Di(heteroatom)-functionalised ferrocenes as [N,N], [O,O] and [S,S] chelate ligands in transition metal chemistry. Chem. Soc. Rev., 34(7): 584.
20. Broderick, E. M. and P. L. Diaconescu. 2009. Cerium(IV) catalysts for the ring-opening polymerization of lactide. Inorg. Chem., 48: 4701-4706.
21. Broderick, E. M., P. Thuy-Boun, N. Guo, C. Vogel, J. Sutter, J. T. Miller, K. Meyer, and P. L. Diaconescu. 2010. Synthesis and characterization of cerium and yttrium alkoxide complexes supported by ferrocene-based chelating ligands. submitted.
22. Shafir, A., D. Fiedler, and J. Arnold. 2002. Formation of 1: 1 complexes of ferrocene-containing salen ligands with Mg, Ti and Zr. J. Chem. Soc., Dalton Trans., 4: 555-560.
23. Holm, R. H., J. G. W. Everett, and A. Chakravorty. 1966. Metal complexes of Schiff bases and beta-Ketoamines. In Prog. Inorg. Chem., Cotton, F. A. (ed.), 7: 83-214.
24. Kapturkiewicz, A. and B. Behr. 1983. Voltammetric studies of Co(salen) and Ni(salen) in nonaqueous solvents at Pt electrode. Inorg. Chim. Acta, 69: 247-251.
25. Zanello, P. and A. Cinquantini. 1985. Electrochemical behaviour of a series of N,N'-1,2-Phenylenebis(salicylideneimin)ato transition metal complexes. Trans. Met. Chem., 10(10): 370-374.
26. Roy, N., S. Sproules, T. Weyhermüller, and K. Wieghardt. 2009. Trivalent iron and ruthenium complexes with a redox noninnocent (2-Mercapto phenylimino)-methyl-4,6-di-tert-butylphenolate(2-) ligand. Inorg. Chem., 48(8): 3783-3791.
27. De Castro, B. and C. Freire. 1990. EPR and electrochemical study of nickel(III) complexes of bis(3,5-dichlorosalicylaldehyde) o-phenylenediimine. Evidence for adduct formation with pyridines. Inorg. Chem., 29(25): 5113-5119.
28. Vilas-Boas, M., C. Freire, B. de Castro, P. A. Christensen, and A. R. Hillman. 1997. New insights into the structure and properties of electroactive polymer films derived from [Ni(salen)]. Inorg. Chem., 36(22): 4919-4929.
29. 2 Schiff-base ligands. J. Chem. Soc., Dalton Trans., 571-576.
30. 2 Schiff-base ligands derived from salicylaldehyde. J. Chem. Soc., Dalton Trans., 1491-1498.
31. 2 Schiff base ligands derived from 2-hydroxy-1-naphthaldehyde. Molecular structure of N,N'-2,3-dimethylbutane-2,3-diyl-bis(2-hydroxy-1-naphthylideneiminate) nickel(II). Inorg. Chim. Acta, 205(2): 157-166.
32. Goldsby, K. A., J. K. Blaho, and L. A. Hoferkamp. 1989. Oxidation of nickel(II) bis(salicylaldimine) complexes: Solvent control of the ultimate redox site. Polyhedron, 8(1): 113-115.
33. 2 Schiff base ligands 2. Crystal and molecular structure of N,N'-l,2-ethane-1-,2-diyl-bis(2- hydroxyacetophenonylideneiminate)nickel(II), N, N'-1,2-cis cyclohexane-1,2-diyl-bis(2-hydroxyacetophenonylideneiminate)- nickel(II) and N,N'-1,2-benzene-1,2-diyl-bis(3,5-dichlorosalicylideneiminate)nickel(II). Inorg. Chim. Acta, 219(1-2): 43-54.
34. Shimazaki, Y., F. Tani, K. I. Fukui, Y. Naruta, and O. Yamauchi. 2003. One-electron oxidized nickel(II)-(disalicylidene)diamine complex: Temperature-dependent tautomerism between Ni(III)-phenolate and Ni(II)-phenoxyl radical states. J. Am. Chem. Soc., 125(35): 10512-10513.
35. Shimazaki, Y., T. Yajima, F. Tani, S. Karasawa, K. Fukui, Y. Naruta, and O. Yamauchi. 2007. Syntheses and electronic structures of one-electronoxidized Group 10 Metal(II)-(Disalicylidene)diamine complexes (metal=Ni, Pd, Pt). J. Am. Chem. Soc., 129(9): 2559-2568.
36. Orio, M., O. Jarjayes, H. Kanso, C. Philouze, F. Neese, and F. Thomas. 2010. X-ray structures of copper(II) and nickel(II) radical salen complexes: The preference of galactose oxidase for copper(II). Angew. Chem. Int. Ed., 49(29): 4989-4992.
37. Yamashita, M., Y. Takemoto, E. Ihara, and H. Yasuda. 1996. Organolanthanide-initiated living polymerizations of ε-Caprolactone, δ-Valerolactone, and β-Propiolactone. Macromolecules, 29: 1798.
38. Hodgson, L. M., A. J. P. White, and C. K. Williams. 2006. Yttrium(III) complex as a highly active catalyst for lactide polymerization. J. Polym. Sci. A: Polym. Chem., 44(22): 6646-6651.
39. Patel, D., S. T. Liddle, S. A. Mungur, M. Rodden, A. J. Blake, and P. L. Arnold. 2006. Bifunctional yttrium(III) and titanium(IV) NHC catalysts for lactide polymerisation. Chem. Commun., 10: 1124-1126.
40. Ma, H., T. P. Spaniol, and J. Okuda. 2008. Rare-earth metal complexes supported by 1,ω-dithiaalkanediyl-bridged Bis(phenolato) ligands: Synthesis, structure, and heteroselective ring-opening polymerization of rac-Lactide. Inorg. Chem., 47(8): 3328-3339.
41. Nomura, N., A. Taira, A. Nakase, T. Tomioka, and M. Okada. 2007. Ring-opening polymerization of lactones by rare-earth metal triflates and by their reusable system in ionic liquids. Tetrahedron, 2007, 63(35): 8478-8484.
42. Shafir, A., M. P. Power, G. D. Whitener, and J. Arnold. 2001. Silylated 1,1'-diaminoferrocene: Ti and Zr complexes of a new chelating diamide ligand. Organometallics, 20(7): 1365-1369.
43. Shafir, A. and J. Arnold. 2003. Zirconium complexes incorporating diaryldiamidoferrocene ligands: generation of cationic derivatives and polymerization activity towards ethylene and 1-hexene. Inorg. Chim. Acta, 345: 216-220.
44. Shafir, A. and J. Arnold. 2003. Ferrocene-based olefin polymerization catalysts: activation, structure, and intermediates. Organometallics, 22(3): 567-575.
45. 2+. J. Am. Chem. Soc., 123(37): 9212-9213.
46. 3. Organometallics, 2: 472-474.
47. Ramos, A., E. Otten, and D. W. Stephan. 2009. Stabilizing Zr and Ti cations by interaction with a ferrocenyl fragment. J. Am. Chem. Soc., 131: 15610-15611.
48. Wrackmeyer, B., E. V. Klimkina, and W. Milius. 2008. Five- and four-coordinate 1,3-Diaza-2-yttria- and 1,3-Diaza-2-scandia-[3]ferrocenophanes. Eur. J. Inorg. Chem., 3340-3347.
49. Eppinger, J., K. R. Nikolaides, M. Zhang-Presse, F. A. Riederer, G. W. Rabe, and A. L. Rheingold. 2008. Alkyl complexes of rare-earth metal centers supported by chelating 1,1'-diamidoferrocene ligands: Synthesis, structure, and application in methacrylate polymerization. Organometallics, 27(4): 736-740.
50. n- metal alkyl complexes supported by chelating diamide ligands. Acc. Chem. Res., 43(10): 1352-1363.
51. Carver, C. T., M. J. Monreal, and P. L. Diaconescu. 2008. Scandium alkyl complexes supported by a ferrocene diamide ligand. Organometallics, 27: 363-370.
52. Carver, C. T. and P. L. Diaconescu. 2008. Ring-opening reactions of aromatic N-heterocycles by scandium and yttrium alkyl complexes. J. Am. Chem. Soc., 130: 7558-7559.
53. Carver, C. T., D. Benitez, K. L. Miller, B. N. Williams, E. Tkatchouk, W. A. Goddard, and P. L. Diaconescu. 2009. Reactions of Group III biheterocyclic complexes. J. Am. Chem. Soc., 131: 10269-10278.
54. Miller, K. L., B. N. Williams, D. Benitez, C. T. Carver, K. R. Ogilby, E. Tkatchouk, W. A. Goddard, and P. L. Diaconescu. 2010. Dearomatization reactions of N-heterocycles mediated by Group 3 complexes. J. Am. Chem. Soc., 132: 342-355.
55. Jie, S. and P. L. Diaconescu. 2010. Reactions of aromatic N-heterocycles with yttrium and lutetium benzyl complexes supported by a pyridine-diamide ligand. Organometallics, 29(5): 1222-1230.
56. Cordero, B., V. Gomez, A. E. Platero-Prats, M. Reves, J. Echeverria, E. Cremades, F. Barragan, and S. Alvarez. 2008. Covalent radii revisited. Dalton Trans., 21: 2832-2838.
57. Wong, A. W., K. L. Miller, and P. L. Diaconescu. 2010. Reactions of aromatic N-heterocycles with a lutetium benzyl complex supported by a ferrocene-diamide ligand. Dalton Trans., 39(29): 6726-6731.
58. Tsuruta, H., T. Imamoto, and K. Yamaguchi. 1999. Evaluation of the relative Lewis acidities of lanthanoid(III) compounds by tandem mass spectrometry. Chem. Commun., 1703-1704.
59. +. Organometallics, 9(7): 2116-2123.
60. Chinchilla, R., C. Najera, and M. Yus. 2004. Metalated heterocycles and their applications in synthetic organic chemistry. Chem. Rev., 104: 2667-2722.
61. Watson, P. L. 1983. Methane exchange reactions of lanthanide and early-transition-metal methyl complexes. J. Am. Chem. Soc., 105(21): 6491-6493.
62. Thompson, M. E., S. M. Baxter, A. R. Bulls, B. J. Burger, M. C. Nolan, B. D. Santarsiero, W. P. Schaefer, and J. E. Bercaw. 1987. σ-Bond metathesis for carbon-hydrogen bonds of hydrocarbons and Sc-R (R=H, alkyl, aryl) bonds of permethylscandocene derivatives. Evidence for noninvolvement of the π system in electrophilic activation of aromatic and vinylic C-H bonds. J. Am. Chem. Soc., 109(1): 203-219.
63. Bercaw, J. E. 1990. Carbon-hydrogen and carbon-carbon bond activation with highly electrophilic transition metal complexes. Pure Appl. Chem., 62(6): 1151-1154.
64. Carver, C. T., B. N. Williams, K. R. Ogilby, and P. L. Diaconescu. 2010. Coupling of aromatic N-heterocycles mediated by Group 3 complexes. Organometallics, 29(4): 835-846.
65. Carver, C. T. and P. L. Diaconescu. 2009. Insertion reactions of scandium pyridyl complexes supported by a ferrocene diamide ligand. J. Alloys Compd., 488(2): 518-523.
66. 2-α-Picolyl compounds. Organometallics, 16: 5506-5516.
67. 2 C-H bond activation chemistry of 2-picoline by Th(IV) and U(IV) metallocene complexes. J. Alloys Compd., 444-445: 477-482.
68. +. Organometallics, 9: 2116-2123.
69. Jantunen, K. C., B. L. Scott, P. J. Hay, J. C. Gordon, and J. L. Kiplinger. 2006. Dearomatization and functionalization of terpyridine by lutetium(III) alkyl complexes. J. Am. Chem. Soc., 128: 6322-6323.
70. D'Souza, D. M. and T. J. J. Muller. 2007. Multi-component syntheses of heterocycles by transition-metal catalysis. Chem. Soc. Rev., 36(7): 1095-1108.
71. Zeni, G. and R. C. Larock. 2004. Synthesis of heterocycles via palladium π-olefin and π-alkyne chemistry. Chem. Rev., 104(5): 2285-2310.
72. Nakamura, I. and Y. Yamamoto. 2004. Transition-metal-catalyzed reactions in heterocyclic synthesis. Chem. Rev., 104(5): 2127-2198.
73. Balme, G., E. Bossharth, and N. Monteiro. 2003. Pd-assisted multicomponent synthesis of heterocycles. Eur. J. Org. Chem., 21: 4101-4111.
74. Davies, H. M. L. and S. J. Hedley. 2007. Intermolecular reactions of electron-rich heterocycles with copper and rhodium carbenoids. Chem. Soc. Rev., 36(7): 1109-1119.
75. Chemler, S. R. and P. H. Fuller. 2007. Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes. Chem. Soc. Rev., 36(7): 1153-1160.
76. Mihovilovic, M. D. and P. Stanetty. 2007. Metal-assisted multicomponent reactions involving carbon monoxide - towards heterocycle synthesis. Angew. Chem. Int. Ed., 46(20): 3612-3615.
77. Padwa, A. and S. K. Bur. 2007. The domino way to heterocycles. Tetrahedron, 63(25): 5341-5378.
78. Jordan, R. F., D. F. Taylor, and N. C. Baenziger. 1990. Synthesis and insertion chemistry of cationic zirconium(IV) pyridyl complexes. Productive σ-bond metathesis. Organometallics, 9(5): 1546-1557.
79. + complexes. Zirconium-mediated functionalization of pyridines. Organometallics, 10(10): 3470-3479.
80. Jordan, R. F. 1991. Chemistry of cationic dicyclopentadienyl group-4 metal alkyl complexes. Adv. Organomet. Chem., 32: 325-387.
81. Lewis, J. C., R. G. Bergman, and J. A. Ellman. 2007. Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation. J. Am. Chem. Soc., 129(17): 5332-5333.
82. Tan, K. L., R. G. Bergman, and J. A. Ellman. 2001. Annulation of alkenyl-substituted heterocycles via rhodium-catalyzed intramolecular C-H activated coupling reactions. J. Am. Chem. Soc., 123(11): 2685-2686.
83. Tan, K. L., R. G. Bergman, and J. A. Ellman. 2002. Intermolecular coupling of isomerizable alkenes to heterocycles via rhodium-catalyzed C-H bond activation. J. Am. Chem. Soc., 124(47): 13964-13965.
84. Tan, K. L., S. Park, J. A. Ellman, and R. G. Bergman. 2004. Intermolecular coupling of alkenes to heterocycles via C-H bond activation. J. Org. Chem., 69(21): 7329-7335.
85. Wiedemann, S. H., R. G. Bergman, and J. A. Ellman. 2004. Rhodium-catalyzed direct C-H addition of 4,4-Dimethyl-2-oxazoline to alkenes. Org. Lett., 6(10): 1685-1687.
86. Wiedemann, S. H., J. A. Ellman, and R. G. Bergman. 2006. Rhodiumcatalyzed direct C-H addition of 3,4-dihydroquinazolines to alkenes and their use in the total synthesis of vasicoline. J. Org. Chem., 71(5): 1969-1976.
87. Kakiuchi, F. and S. Murai. 2002. Catalytic C-H/olefin coupling. Acc. Chem. Res., 35(10): 826-834.
88. Fujii, N. K. F., N. Chatani, and S. Murai. 1996. Transition metal-catalyzed intramolecular C-H/olefin coupling. Chem. Lett., 939-940.
89. Fujii, N. K. F., A. Yamada, N. Chatani, and S. Murai. 1997. Asymmetric intramolecular C-H/olefin coupling: asymmetric cyclization reactions of 1,5-dienes catalyzed by rhodium complexes. Chem. Lett., 425-426.
90. Fujii, N. K. F., A. Yamada, N. Chatani, and S. Murai. 1998. Transition metal-catalyzed intramolecular cyclization of 1,5- and 1,6-dienes via direct cleavage and addition of the carbon-hydrogen bond. Bull. Chem. Soc. Jpn., 71: 285-298.
91. Zhang, Z., X. Wang, and R. A. Widenhoefer. 2006. Platinum(II)-catalyzed intermolecular hydroarylation of unactivated alkenes with indoles. Chem. Commun., 35: 3717-3719.
92. Liu, C., X. Han, X. Wang, and R. A. Widenhoefer. 2004. Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins. J. Am. Chem. Soc., 126(12): 3700-3701.
93. Han, X. and R. A. Widenhoefer. 2006. Platinum-catalyzed intramolecular asymmetric hydroarylation of unactivated alkenes with indoles. Org. Lett., 8(17): 3801-3804.
94. Jordan, R. F. and D. F. Taylor. 1989. Zirconium-catalyzed coupling of propene and α-picoline. J. Am. Chem. Soc., 111(2): 778-779.
95. +: facile zirconium-mediated functionalization of methyl carbon-hydrogen bonds of 2,6-lutidine. J. Am. Chem. Soc., 113(5): 1833-1835.
96. 2). Organometallics, 13(10): 3881-3891.
97. 0 metallocenes. Organometallics, 18(8): 1389-1401.
98. Monreal, M. J. and P. L. Diaconescu. 2010. Reversible C-C coupling in a uranium biheterocyclic complex. J. Am. Chem. Soc., 132(22): 7676-7683.
99. Miller, K. L., C. T. Carver, B. N. Williams, and P. L. Diaconescu. 2010. Reactions of imidazoles with electrophilic metal alkyl complexes. Organometallics, 29(10): 2272-2281.
100. Allen, K. D., M. A. Bruck, S. D. Gray, R. P. Kingsborough, D. P. Smith, K. J. Weller, and D. E. Wigley. 1995. Quinoline binding mode as a function of oxidation state in aryloxide-supported tantalum complexes: Models for hydrodenitrogenation catalysis. Polyhedron, 14(22): 3315-3333.
101. 3SiO). J. Am. Chem. Soc., 119(1): 247-248.
102. 3SiO-). J. Am. Chem. Soc., 110(13): 4421-4423.
103. Fout, A. R., B. C. Bailey, J. Tomaszewski, and D. J. Mindiola. 2007. Cyclic denitrogenation of N-heterocycles applying a homogeneous titanium reagent. J. Am. Chem. Soc., 129(42): 12640-12641.
104. Bailey, B. C., H. Fan, J. C. Huffman, M. H. Baik, and D. J. Mindiola. 2006. Room temperature ring-opening metathesis of pyridines by a transient TiC linkage. J. Am. Chem. Soc., 128(21): 6798-6799.
105. Huertos, M. A., J. Perez, and L. Riera. 2008. Pyridine ring opening at room temperature at a rhenium tricarbonyl bipyridine complex. J. Am. Chem. Soc., 130(17): 5662-5663.
106. Huertos, M. A., J. Pérez, L. Riera, and A. Menéndez-Velaázquez. 2008. From N-Alkylimidazole ligands at a rhenium center: ring opening or formation of NHC complexes. J. Am. Chem. Soc., 130(41): 13530-13531.
107. Sattler, A. and G. Parkin. 2010. Cleaving carbon-carbon bonds by inserting tungsten into unstrained aromatic rings. Nature, 463: 523-526.
108. Monreal, M. J., S. Khan, and P. L. Diaconescu. 2009. Beyond C-H activation with uranium: A cascade of reactions mediated by a uranium dialkyl complex. Angew. Chem. Int. Ed., 48(44): 8352-8355.
109. Duhović, S., M. J. Monreal, and P. L. Diaconescu. 2010. Reactions of aromatic heterocycles with uranium alkyl complexes. Inorg. Chem., 49(15): 7165-7169.
110. Duhović, S., M. J. Monreal, and P. L. Diaconescu. 2010. Ring opening of aromatic heterocycles by uranium complexes. J. Organomet. Chem., Pacifichem 2010, DOI:10.1016=j.jorganchem.2010.08.003.
111. Pool, J. A., B. L. Scott, and J. L. Kiplinger. 2005. Carbon-nitrogen bond cleavage in pyridine ring systems mediated by organometallic thorium(IV) complexes. Chem. Commun., 20: 2591-2593.
112. Arunachalampillai, A., P. Crewdson, I. Korobkov, and S. Gambarotta. 2006. Ring opening and C-O and C-N bond cleavage by transient reduced thorium species. Organometallics, 25: 3856-3866.
113. Huang, W., C. T. Carver, and P. L. Diaconescu. 2010. Transmetallation reactions of a scandium complex supported by a ferrocene-diamide ligand. Inorg. Chem., in press.
114. Williams, B. N., W. Huang, K. L. Miller, and P. L. Diaconescu. 2010. Group 3 metal complexes of radical-anionic 2,2'-bipyridyl ligands. Inorg. Chem., in press.
115. Parenty, A. D. C., L. V. Smith, A. L. Pickering, D.-L. Long, and L. Cronin. 2004. General one-pot, three-step methodology leading to an extended class of n-heterocyclic cations: spontaneous nucleophilic addition, cyclization, and hydride loss. J. Org. Chem., 69: 5934-5946.
116. Cha, J. S. 2006.Recent developments in Meerwein-Ponndorf-Verley and related reactions for the reduction of organic functional groups using aluminum, boron, and other metal reagents: a review. Org. Proc. Res. Dev., 10: 1032-1053.