Efficient H-D exchange reactions using heterogeneous platinum-group metal on carbon-HD system

Synlett

Volumn 23, Issue 7, 2012, Pages 959-972

  Sawama, Yoshinari ^a   Monguchi, Yasunari ^a   Sajiki, Hironao ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Dgas; H D exchange; heterogeneous catalysis; isotope labeling; platinum group metals

Indexed keywords

AGRICULTURAL CHEMICAL; ALKANE DERIVATIVE; ALKANOL; ALKYLBENZENE; AMINO ACID; CARBOHYDRATE; CARBON; DEUTERIUM; DEUTERIUM OXIDE; HETEROCYCLIC COMPOUND; HYDROCHLORIC ACID; HYDROGEN; NUCLEIC ACID; PALLADIUM; PLATINUM; PLATINUM DERIVATIVE; RHENIUM; RUTHENIUM; SILANE DERIVATIVE; TERT BUTYLDIMETHYLSILYL ETHER; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEUTERIUM HYDROGEN EXCHANGE; HIGH TEMPERATURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 84859809777     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289696     Document Type: Article

References (141)

1. Urey HC, Brickwedde FG, Murphy GM. Phys. Rev.: 1932; 40 1
2. Tokuhisa S, Saisu K, Yoshikawa H, Tsuda T, Morishita T, Baba S. Chem. Pharm. Bull.: 1978; 26 3647
3. Foster AB. Trends Pharmacol. Sci.: 1984; 524
4. Murray S, Lynch AM, Knize MG, Gooderham NJ. J. Chromatogr.: 1993; 616 211
5. Lewis RG, Fortune CR, Willis RD, Camann DE, Antley JT. Environ. Health Perspect.: 1999; 107 721
6. Rudel RA, Camann DE, Spengler JD, Korn LR, Brody JG. Environ. Sci. Technol.: 2003; 37 4543
7. Stokvis E, Rosing H, Beijnen JH. Rapid Commun. Mass Spectrom.: 2005; 19 401
8. Gardner KH, Kay LE. J. Am. Chem. Soc.: 1997; 119 7599
9. Sack I, Balazs YS, Rahimipour S, Vega S. J. Am. Chem. Soc.: 2000; 122 12263
10. Takeda M, Jee J, Ono A, Terauchi T, Kainosho M. J. Am. Chem. Soc.: 2009; 131 18556
11. Lowry TH, Richardson KS. Mechanism and Theory in Organic Chemistry. Harper and Row New York: 1987
12. Furuta T, Takahashi H, Kasuya Y. J. Am. Chem. Soc.: 1990; 112 3633
13. Porter DJ. T, Boyd FL. J. Biol. Chem.: 1991; 266 21616
14. Chou M.-Y, Mandal AB, Leung M.-K. J. Org. Chem.: 2002; 67 1501
15. Oh CH, Jung HH, Kim KS, Kim N. Angew. Chem. Int. Ed.: 2003; 42 805
16. Marcus DM, Hayman MJ, Blau YM, Guenther DR, Ehresmann JO, Kletnieks PW, Haw JF. Angew. Chem. Int. Ed.: 2006; 45 1933
17. Marcus DM, McLachlan KA, Wildman MA, Ehresmann JO, Kletnieks PW, Haw JF. Angew. Chem. Int. Ed.: 2006; 45 3133
18. Perrin CL, Dong Y. J. Am. Chem. Soc.: 2007; 129 4490
19. Russell TP, Karim A, Mansour A, Felcher GP. Macromolecules: 1988; 21 1890
20. Tead SF, Kramer EJ, Russell TP, Volksen W. Polymer: 1992; 33 3382
21. Okazaki M, Uchino N, Nozaki N, Kubo K. Bull. Chem. Soc. Jpn.: 1995; 68 1024
22. Stoffel NC, Chandra S, Kramer EJ. Polymer: 1997; 38 5073
23. Kondo A, Ishigure TKoike Y. J. Lightwave Technol.: 2005; 23 2443
24. Atzrodt J, Derdau V, Fey T, Zimmermann J. Angew. Chem. Int. Ed.: 2007; 46 7744
25. Herbert JM. J. Labelled Compd. Radiopharm: 2010; 53 658
26. Werstiuk NH, Kadai T. Can. J. Chem.: 1974; 52 2169
27. Werstiuk NH, Timmins G. Can. J. Chem.: 1981; 59 3218
28. Grose KR, Kim IS, Bjeldanes LF. J. Agric. Food Chem.: 1982; 30 766
29. Gaston MH, Skidmore DR. Org. Prep. Proced. Int.: 1985; 17 138
30. Werstiuk NH, Timmins G. Can. J. Chem.: 1989; 67 1744
31. Kawazoe Y, Ohnishi M, Yoshioka Y. Chem. Pharm. Bull.: 1964; 12 1384
32. Beak P, Monroe EM. J. Org. Chem.: 1969; 34 589
33. Kawazoe Y, Ohnishi M, Yoshioka Y. Chem. Pharm. Bull.: 1967; 15 1225
34. Feldman D, Halpern M, Rabinovitz M. J. Org. Chem.: 1985; 50 1746
35. Castell JV, Martnez LA, Miranda MA, Trrega P. J. Labelled Compd. Radiopharm.: 1994; 34 93
36. Lygo B, Humphreys LD. Tetrahedron Lett.: 2002; 43 6677
37. Rubottom GM, Evain EJ. Tetrahdron: 1990; 46 5055
38. Ogasawara M, Saburi M. Organometallics: 1994; 13 1911
39. Collman JP, Fish HT, Wagenknecht PS, Tyvoll DA, Chng L.-L, Eberspacher TA, Brauman JI, Bacon JW, Pignolet LH. Inorg. Chem.: 1996; 35 6746
40. Calf GE, Garnett JL. Chem. Commun.: 1967; 306
41. Weil TA, Friedman S, Wender I. J. Org. Chem.: 1974; 39 48
42. Tsukinoki T, Ishimoto K, Mukumoto M, Suzuki M, Kawaji T, Nagano Y, Tsuzuki H, Mataka S, Tashiro M. J. Chem. Res., Synop.: 1996; 66
43. Mukumoto M, Tsuzuki H, Mataka S, Tashiro M, Tsukinoki T, Nagano Y. Chem. Lett.: 1996; 165
44. Lenges CP, Brookhart M, Grant BE. J. Organomet. Chem.: 1997; 528 199
45. Seiwell LP. J. Am. Chem. Soc.: 1974; 96 7134
46. Blake MR, Garnett JL, Gregor IK, Hannan W, Hoa K, Long MA. J. Chem. Soc., Chem. Commun.: 1975; 930
47. Rozzell JD. Tetrahedron Lett.: 1982; 23 1767
48. Lockley WJ. S. Tetrahedron Lett.: 1982; 23 3819
49. Blum J, Amer I, Vollhardt KP. C, Schwarz H, Hoehne G. J. Org. Chem.: 1987; 52 2804
50. Hesk D, Jones JR, Lockley WJ. S. J. Pharm. Sci.: 1991; 80 887
51. Takehara DK, Butt JB, Burwell RL. Jr. J. Catal.: 1992; 113 279
52. Takehara DK, Butt JB, Burwell RL. Jr. J. Catal.: 1992; 133 294
53. Lenges CP, White PS, Brookhart M. J. Am. Chem. Soc.: 1999; 121 4385
54. Rybtchinski B, Cohen R, Ben-David Y, Martin JM. L, Milstein D. J. Am. Chem. Soc.: 2003; 125 11041
55. Faller JW, Smart CJ. Organometallics: 1989; 8 602
56. Heys R. J. Chem. Soc., Chem. Commun.: 1992; 680
57. Heys JR, Shu AY. L, Senderoff SG, Phillips NM. J. Labelled Compds. Radiopharm.: 1993; 33 431
58. Hesk D, Das PR, Evans B. J. Labelled Compds. Radiopharm.: 1995; 36 497
59. Lukey CA, Long MA, Garnett JL. Aust. J. Chem.: 1995; 48 79
60. Golden JT, Andersen RA, Bergman RG. J. Am. Chem. Soc.: 2001; 123 5837
61. Ellames GJ, Gibson JS, Herbert JM, Kerr WJ, McNeill AH. Tetrahedron Lett.: 2001; 42 6413
62. Klei SR, Golden JT, Tilley TD, Bergman RG. J. Am. Chem. Soc.: 2002; 124 2092
63. Hickey MJ, Jones JR, Kingston LP, Lockley WJ. S, Mather AN, McAuley BM, Wilkinson DJ. Tetrahedron Lett.: 2003; 44 3959
64. Hickey MJ, Jones JR, Kingston LP, Lockley WJ. S, Mather AN, Wilkinson DJ. Tetrahedron Lett.: 2004; 45 8621
65. Skaddan MB, Yung CM, Bergman RG. Org. Lett.: 2004; 6 11
66. Yung CM, Skaddan MB, Bergman RG. J. Am. Chem. Soc.: 2004; 126 13033
67. Garman RN, Hickey MJ, Kingston LP, McAuley B, Jones JR, Lockley WJ. S, Mather AN, Wilkinson DJ. J. Labelled Compd. Radiopharm.: 2005; 48 75
68. Corbern R, Sana M, Peris E. J. Am. Chem. Soc.: 2006; 128 3974
69. Macdonald CG, Shannon JS. Tetrahedron Lett.: 1964; 45 3351
70. Wu GD, Serianni AS, Barker R. J. Org. Chem.: 1983; 48 1750
71. Pojer PM. Tetrahedron Lett.: 1984; 25 2507
72. Angyal SJ, Stevens JD. Carbohydr. Res.: 1986; 157 83
73. Angyal SJ, Stevens JD. Carbohydr. Res.: 1987; 169 151
74. Pathak T, Chattopadhyaya J. Tetrahedron: 1987; 43 4227
75. Tsuzuki H, Mukumoto M, Mataka S, Yonemitsu T, Tashiro M. J. Chem. Res., Synop.: 1993; 144
76. Schrage K, Burwell RL. Jr. J. Am. Chem. Soc.: 1966; 88 4555
77. Atkinson JG, Luke MO, Stuart RS. Can. J. Chem.: 1967; 45 1511
78. Hsiao CY. Y, Ottaway CA, Wetlaufer DB. Lipids: 1974; 9 913
79. Ofosu-Asante K, Stock LM. J. Org. Chem.: 1986; 51 5452
80. Kiritani R, Asano T, Fujita S, Dohmaru T, Kawanishi T. J. Labelled Compd. Radiopharm.: 1986; 23 207
81. Azran J, Shimoni M, Buchman O. J. Catal.: 1994; 148 648
82. Hardacre C, Holbrey JD, McMath SE. J. Chem. Commun.: 2001; 367
83. Garnett JL, Sollich WA. Aust. J. Chem.: 1961; 14 441
84. Garnett JL, Henderson LJ, Sollich WA, Tiers GV. D. Tetrahedron Lett.: 1961; 15 516
85. Fraser RR, Renaud RN. J. Am. Chem. Soc.: 1966; 88 4365
86. Garnett JL, Hodges RJ. J. Am. Chem. Soc.: 1967; 89 4546
87. Garnett JL, Hodges RJ. Chem. Commun.: 1967; 1001
88. Gol'dshleger NF, Tyabin MB, Shilov AE, Shteinman AA. Zh. Fiz. Khim.: 1969; 43 1222
89. Hodges RJ, Webster DE, Wells PB. J. Chem. Res. (A): 1971; 3230
90. Hodges RJ, Webster DE, Wells PB. Chem. Commun.: 1971; 462
91. Garnett JL, Kenyon RS. J. Chem. Soc. D: 1971; 1227
92. Hodges RJ, Webster DE, Wells PB. J. Chem. Soc., Dalton Trans.: 1972; 2571
93. Hodges RJ, Webster DE, Wells PB. J. Chem. Soc., Dalton Trans.: 1972; 2577
94. Matsuo M, Matsuo T, Deguchi T, Kashida Y. Chem. Pharm. Bull.: 1972; 20 990
95. Maeda M, Kawazoe Y. Tetrahedron Lett.: 1975; 19 1643
96. Kramer PA, Masters C. J. Chem. Soc., Dalton Trans.: 1975; 849
97. Kiffen AA, Masters C, Raynand L. J. Chem. Soc., Dalton Trans.: 1975; 853
98. Maeda M, Ogawa O, Kawazoe Y. Chem. Pharm. Bull.: 1977; 25 3329
99. Räisänen M, Kärkkäinen J. Acta Chem. Scand. B: 1979; 33 11
100. Asscher Y, Ferraiolo B, Castagnoli NJr. J. Org. Chem.: 1984; 49 3138
101. Buncel E, Clement O. J. Chem. Soc., Perkin Trans. 2: 1995; 1333
102. Derdau V, Atzrodt J. Synlett: 2006; 1918
103. Derdau V, Atzrodt J, Zimmermann J, Kroll C, Brückner F. Chem. Eur. J.: 2009; 15 10397
104. Yao J, Evilia RF. J. Am. Chem. Soc.: 1994; 116 11229
105. Kuhlmann B, Arnett EM, Siskin M. J. Org. Chem.: 1994; 59 3098
106. Junk T, Catallo WJ. Tetrahedron Lett.: 1996; 37 3445
107. Yang Y, Evilia RF. J. Supercrit. Fluids: 1996; 9 161
108. Junk T, Catallo WJ, Civils LD. J. Labelled Compd. Radiopharm.: 1997; 39 625
109. Junk T, Catallo WJ, Elguero J. Tetrahedron Lett.: 1997; 38 6309
110. Yang Y, Evilia RF. J. Supercrit. Fluids: 1999; 15 165
111. Kalpala J, Hartonen K, Huhdanpää M, Riekkola M.-L. Green Chem.: 2003; 5 670
112. Browne WR, O'Connor CM, Killeen JS, Guckian AL, Burke M, James P, Burke M, Vos JG. Inorg. Chem.: 2002; 41 4245
113. Matsubara S, Yokota Y, Oshima K. Chem. Lett.: 2004; 33 294
114. Yamamoto M, Oshima K, Matsubara S. Chem. Lett.: 2004; 33 846
115. Yamamoto M, Yokota Y, Oshima K, Matsubara S. Chem. Commun.: 2004; 1714
116. Matsubara S, Yokota Y, Oshima K. Org. Lett.: 2004; 6 2071
117. Yamamoto M, Oshima K, Matsubara S. Org. Lett.: 2004; 6 5015
118. Yamamoto M, Oshima K, Matsubara S. Heterocycles: 2006; 67 353
119. Barthez JM, Filikov AV, Frederiksen LB, Huguet M.-L, Jones JR, Lu S.-Y. Can. J. Chem.: 1998; 76 726
120. Elander N, Jones JR, Lu S.-Y, Stone-Elander S. Chem. Soc. Rev.: 2000; 29 239
121. Fodor-Csorba K, Galli G, Holly S, Gcs-Baitz E. Tetrahedron Lett.: 2002; 43 3789
122. Takahashi M, Oshima K, Matsubara S. Chem. Lett.: 2005; 34 192
123. Ishibashi K, Takahashi M, Yokota Y, Oshima K, Matsubara S. Chem. Lett.: 2005; 34 664
124. Martins A, Lautens M. Org. Lett.: 2008; 10 4351
125. Sajiki H, Kurita T, Esaki H, Aoki F, Maegawa T, Hirota K. Org. Lett.: 2004; 6 3521
126. Kurita T, Aoki F, Mizumoto T, Maejima T, Esaki H, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J.: 2008; 14 3371
127. Hattori K, Sajiki H, Hirota K. Tetrahedron Lett.: 2000; 41 5711
128. Hattori K, Sajiki H, Hirota K. Tetrahedron: 2001; 57 2109
129. Sajiki H, Hattori K, Aoki F, Yasunaga K, Hirota K. Synlett: 2002; 1149
130. Kurita T, Hattori K, Seki S, Mizumoto T, Aoki F, Yamada Y, Ikawa K, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J.: 2008; 14 664
131. Sajiki H, Aoki F, Esaki H, Maegawa T, Hirota K. Org. Lett.: 2004; 6 1485
132. Maegawa T, Akashi A, Esaki H, Aoki F, Sajiki H, Hirota K. Synlett: 2005; 845
133. Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K. Synlett: 2005; 1385
134. Esaki H, Aoki F, Maegawa T, Hirota K, Sajiki H. Heterocycles: 2005; 66 361
135. Esaki H, Ito N, Sakai S, Maegawa T, Monguchi Y, Sajiki H. Tetrahedron: 2006; 62 10954
136. Esaki H, Aoki F, Umemura M, Kato M, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J.: 2007; 13 4052
137. Esaki H, Ohtaki R, Maegawa T, Monguchi Y, Sajiki H. J. Org. Chem.: 2007; 72 2143
138. Sajiki H, Ito N, Esaki H, Maesawa T, Maegawa T, Hirota K. Tetrahedron Lett.: 2005; 46 6995
139. Ito N, Esaki H, Maesawa T, Imamiya E, Maegawa T, Sajiki H. Bull. Chem. Soc. Jpn.: 2008; 81 278
140. Ito N, Watahiki T, Maesawa T, Maegawa T, Sajiki H. Adv. Synth. Catal.: 2006; 348 1025
141. Ito N, Watahiki T, Maesawa T, Maegawa T, Sajiki H. Synthesis: 2008; 1467