Avoiding CO2 in catalysis of decarboxylation

Advances in Physical Organic Chemistry

Volumn 47, Issue , 2013, Pages 85-128

  Kluger, Ronald ^a   Howe, Graeme W ^a   Mundle, Scott O C ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Acid catalysis; Addition; Aromatic decarboxylation; Associative mechanisms; Base catalysis; Decarboxylation; Direct formation of bicarbonate; Formation of protonated carbonic acid; Overcoming reversibility

Indexed keywords

EID: 84888391804     PISSN: 00653160     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-407754-6.00002-8     Document Type: Chapter

References (150)

1. B.R. Brown Q Rev Chem Soc 5 1951 131 146
2. L.W. Clark S. Patai, The Chemistry of Functional Groups 1969 John Wiley & Sons, Ltd. London
3. W.I. Dzik, P.P. Lange, and L. Gooßen Chem Sci 3 2012 2671 2678
4. Y. Pan, and C. Tan Synthesis 2011 2044 2053
5. R. Kluger Chem Rev 87 1987 863 876
6. D.A. Shirley Organic Chemistry 1966 Holt, Rinehart and Winston, Inc. New York
7. A.V. Willi, C.M. Won, and P. Vilk J Phys Chem 72 1968 3142 3148
8. G.E. Dunn, and G.K.J. Lee Can J Chem 49 1971 1032 1035
9. G.E. Dunn, and S.K. Dayal Can J Chem 48 1970 3349 3353
10. S.O.C. Mundle, and R. Kluger J Am Chem Soc 131 2009 11674 11675
11. S.O.C. Mundle, G. Lacrampe-Couloume, B.S. Lollar, and R. Kluger J Am Chem Soc 132 2010 2430 2436
12. M.H. O'Leary Acc Chem Res 21 1988 450 455
13. R. Kluger, and S.O.C. Mundle Adv Phys Org Chem 44 2010 357 375
14. J. Hong, S. Sun, T. Derrick, C. Larive, K.B. Schowen, and R.L. Schowen Biochim Biophys Acta 1385 1998 187 200
15. I.A. Klages, and G. Lickroth Ber Dtsch Chem Ges 32 1899 1549 1565
16. J.J. Carroll, J.D. Slupsky, and A.E. Mather J Phys Chem Ref Data 20 1991 1201 1209
17. Z. Duan, and R. Sun Chem Geol 193 2003 257 271
18. H. Sato, N. Matubayasi, M. Nakahara, and F. Hirata Chem Phys Lett 323 2000 257 262
19. J.P. Richard, and T.L. Amyes Bioorg Chem 32 2004 354 366
20. P.V. Attwood, and J.C. Wallace Acc Chem Res 35 2002 113 120
21. A. Radzicka, and R. Wolfenden Science 267 1995 90 93
22. G.K. Lee, and K.N. Houk Science 276 1997 942 945
23. R.B. Silverman, and M.P. Groziak J Am Chem Soc 104 1982 6434 6439
24. P. Beak, and B. Siegel J Am Chem Soc 98 1976 3601 3606
25. N. Wu, W. Gillon, and E.F. Pai Biochemistry 41 2002 4002 4011
26. A. Warshel, M. Štrajbl, J. Villà, and J. Florián Biochemistry 39 2000 14728 14738
27. B.P. Callahan, and B.G. Miller Bioorg Chem 35 2007 465 469
28. B.P. Callahan, and R. Wolfenden J Am Chem Soc 126 2004 14698 14699
29. T.C. Appleby, C. Kinsland, T.P. Begley, and S.E. Ealick Proc Natl Acad Sci U S A 97 2000 2005 2010
30. A. Warshel, P.K. Sharma, M. Kato, Y. Xiang, H. Liu, and M.H.M. Olsson Chem Rev 106 2006 3210 3235
31. R. Kluger, G. Ikeda, Q. Hu, P. Cao, and J. Drewry J Am Chem Soc 128 2006 15856 15864
32. Q. Hu, and R. Kluger J Am Chem Soc 127 2005 12242 12243
33. Q. Hu, and R. Kluger J Am Chem Soc 126 2004 68 69
34. Q. Hu, and R. Kluger J Am Chem Soc 124 2002 14858 14859
35. R. Kluger, and T. Smyth J Am Chem Soc 103 1981 1214 1216
36. R. Kluger, J. Chin, and T. Smyth J Am Chem Soc 103 1981 884 888
37. R.N. Rosenfeld, and B.R. Weiner J Org Chem 48 1983 5362 5364
38. R. Kakkar, M. Pathak, and N.P. Radhika Org Biomol Chem 4 2006 886 895
39. F. Jordan, and Y.H. Mariam J Am Chem Soc 102 1980 7618
40. F. Jordan, and Y.H. Mariam J Am Chem Soc 100 1978 2534 2541
41. E.S. Polovnikova, M.J. McLeish, and E.A. Sergienko Biochemistry 42 2003 1820 1830
42. I. Baburina, Y. Gao, Z. Hu, F. Jordan, S. Hohmann, and W. Furey Biochemistry 33 1994 5630 5635
43. J. Crosby, R. Stone, and G.E. Lienhard J Am Chem Soc 92 1970 2891 2900
44. J. Crosby, and G.E. Lienhard J Am Chem Soc 92 1970 5707 5716
45. R. Kluger, and D. Yu Bioorg Chem 34 2006 337 344
46. G.S. Brandt, M.M. Kneen, and S. Chakraborty Biochemistry 48 2009 3247 3257
47. G.S. Brandt, M.M. Kneen, G.A. Petsko, D. Ringe, and M.J. McLeish J Am Chem Soc 132 2010 438 439
48. R. Kluger, and K. Tittmann Chem Rev 108 2008 1797 1833
49. H. Patel, N.S. Nemeria, L.A. Brammer, C.L. Freel Meyers, and F. Jordan J Am Chem Soc 134 2012 18374 18379
50. D. Meyer, P. Neumann, and C. Parthier Biochemistry 49 2010 8197 8212
51. M. Bruning, M. Berheide, and D. Meyer Biochemistry 48 2009 3258 3268
52. W.P. Jencks A. Meister, Adv Enzymol 43 1975 219 410
53. C.A.J. Lewis, and R. Wolfenden Proc Natl Acad Sci U S A 105 2008 17328 17333
54. X. Zhang, and K.N. Houk Acc Chem Res 38 2005 379 385
55. K. Saito, G. Sasaki, K. Okada, and S. Tanaka J Phys Chem 98 1994 3756 3761
56. L.K. Jackson, H.B. Brooks, D.P. Myers, and M.A. Phillips Biochemistry 42 2003 2933 2940
57. J.P. Guthrie, and F. Jordan J Am Chem Soc 94 1972 9136 9141
58. R.W. Hay Aust J Chem 18 1965 337 351
59. R. Steinberger, and F.H. Westheimer J Am Chem Soc 73 1951 429 435
60. F.H. Westheimer, and W.A. Jones J Am Chem Soc 63 1941 3283 3286
61. C.K. Sauers, W.P. Jencks, and S. Groh J Am Chem Soc 97 1975 5546 5553
62. D.T. Major, and J. Gao J Chem Theory Comput 3 2007 949 960
63. J. Gao, S. Ma, D.T. Major, K. Nam, J. Pu, and D.G. Truhlar Chem Rev 106 2006 3188 3209
64. N. Wu, Y. Mo, J. Gao, and E.F. Pai Proc Natl Acad Sci U S A 97 2000 2017 2022
65. S.O.C. Mundle, G.W. Howe, and R. Kluger J Am Chem Soc 134 2012 1066 1070
66. C.F. Bernasconi Adv Phys Org Chem. 44 2010 223 324
67. C.F. Bernasconi Tetrahedron 41 1985 3219 3234
68. C.F. Bernasconi Acc Chem Res 25 1992 9 16
69. E.V. Brown, and R.J. Moser J Org Chem 36 1971 454 457
70. A. Thomson J Chem Soc B 1970 1198 1201
71. R.W. Hay, and K.R. Tate Aust J Chem 23 1970 1407 1413
72. D.B. Bigley, and R.W. May J Chem Soc B 1969 994 995
73. G.E. Dunn, E.G. Janzen, and W. Rodewald Can J Chem 46 1968 2905 2909
74. F.M. Beringer, and S. Sands J Am Chem Soc 75 1953 3319 3322
75. C.F. Bernasconi, and J. Fassberg J Am Chem Soc 116 1994 514 522
76. A.J. Kresge Chem Soc Rev 2 1973 475 503
77. W. Wu, S. Shaik, and W.H.J. Saunders J Org Chem 75 2010 3722 3728
78. J.P. Guthrie Adv Phys Org Chem 45 2011 171 220
79. J.P. Guthrie, S. Peiris, M. Simkin, and Y. Wang Can J Chem 88 2010 79 98
80. J.P. Guthrie Bioorg Chem 30 2002 32 52
81. D.J. Cram, and P. Haberfield J Am Chem Soc 83 1961 2354 2362
82. J.P. Guthrie Can J Chem 77 1999 934 942
83. R. Battino, and H.L. Clever Chem Rev 66 1966 395 463
84. G. Houghton, A.M. McLean, and P.D. Ritchie Chem Eng Sci 6 1957 132 137
85. G.K. Anderson J Chem Thermodyn 35 2003 1171 1183
86. V. Rubio Biosci Rep 6 1986 335 347
87. Y. Kaziro, L.F. Hass, P.D. Boyer, and S. Ochoa J Biol Chem 237 1962 1460 1468
88. T.G. Cooper, and H.G. Wood J Biol Chem 246 1971 5488 5490
89. J.R. Knowles Annu Rev Biochem 58 1989 195 221
90. S.D. Taylor, and R. Kluger J Am Chem Soc 115 1993 867 871
91. S.L. Johnson Adv Phys Org Chem 5 1967 237 330
92. D. Samuel, and B.L. Silver Adv Phys Org Chem 3 1965 123 186
93. A.A. Vandersteen, S.O.C. Mundle, and R. Kluger J Org Chem 77 2012 6505 6509
94. J.C. Traeger, and B.M. Kompe Org Mass Spectrom 26 1991 209 214
95. G.E. Dunn, G.K.J. Lee, and H. Thimm Can J Chem 50 1972 3017 3027
96. G.E. Dunn, P. Leggate, and I.E. Scheffler Can J Chem 43 1965 3080 3094
97. W.M. Schubert, J. Donohue, and J.D. Gardner J Am Chem Soc 76 1954 9 14
98. W.M. Schubert J Am Chem Soc 71 1949 2639 2644
99. L. Hine, and G.F. Koser J Org Chem 36 1971 3591 3593
100. J. Hine, and N.W. Flachskam J Org Chem 42 1977 1979 1981
101. J.P. Guthrie, and P.A. Cullimore Can J Chem 58 1980 1281 1294
102. J.L. Longridge, and F.A. Long J Am Chem Soc 90 1968 3092 3098
103. G.A. Olah, and A.M. White J Am Chem Soc 90 1968 1884 1889
104. S. Warren, and M.R. Williams J Chem Soc B 1971 618 621
105. I. Roberts, and H.C. Urey J Am Chem Soc 61 1939 2580 2584
106. C.A. Bunton, D.H. James, and J.B. Senior J Chem Soc 1960 3364 3367
107. R.L. Redington J Phys Chem 80 1976 229 235
108. T.D. Lomax, and C. O'Connor J Am Chem Soc 100 1978 5910 5914
109. C. O'Connor J Inorg Nucl Chem 30 1968 2697 2708
110. C. O'Connor, and T.A. Turney J Chem Soc B 1966 1211 1217
111. C. O'Connor, and D.R. LLewellyn J Chem Soc 1965 2669 2673
112. C. O'Connor, and D.R. LLewellyn J Chem Soc 1965 2197 2201
113. D.R. Llewellyn, and C. O'Connor J Chem Soc 1964 4400 4404
114. D.R. Llewellyn, and C. O'Connor J Chem Soc 1964 545 549
115. J. Hipkin, and D.P.N. Satchell Tetrahedron 21 1965 835 842
116. C. Hansch, A. Leo, and R.W. Taft Chem Rev 91 1991 165 195
117. G. Kortüm, W. Vogel, and K. Andrussow Pure Appl Chem 1 1960 187 536
118. S.O.C. Mundle, A.A. Vandersteen, G. Lacrampe-Couloume, R. Kluger, and B.S. Lollar Rapid Commun Mass Spectrom 27 2013 1778 1784
119. P. Gerbaux, and F. Turecek J Phys Chem A 106 2002 5938 5950
120. T. Loerting, C. Tautermann, and R.T. Kroemer Angew Chem Int Ed 39 2000 891 894
121. S.O.C. Mundle, L. Guevara Opiñska, R. Kluger, and A.P. Dicks J Chem Educ 88 2011 1004 1006
122. A.A. Bothner-By, and J. Bigeleisen J Chem Phys 19 1951 755 759
123. G.W. Howe, M. Bielecki, and R. Kluger J Am Chem Soc 134 2012 20621 20623
124. S.O.C. Mundle, S. Rathgeber, G. Lacrampe-Couloume, B.S. Lollar, and R. Kluger J Am Chem Soc 131 2009 11638 11639
125. A. Häußermann, F. Rominger, and B.F. Straub Chem Eur J 18 2012 14174 14185
126. D. Stefanidis, and W.P. Jencks J Am Chem Soc 115 1993 6045 6050
127. F. Hibbert Comprehensive Chemical Kinetics vol. 8 1977 Elsevier Oxford 97 197
128. R.H. DeWolfe A.T. Blomquist, Synthesis and Properties of Carboxylic Ortho Esters and Related Compounds vol. 14 1970 Academic Press London
129. J.P. Guthrie, and V. Pitchko J Am Chem Soc 122 2000 5520 5528
130. J.P. Guthrie J Am Chem Soc 122 2000 5529 5538
131. J.P. Guthrie, J. Barker, P.A. Cullimore, J. Lu, and D.C. Pike Can J Chem 71 1993 2109 2122
132. J.P. Guthrie J Am Chem Soc 95 1973 6999 7003
133. R. Kluger, and I.F. Moore J Am Chem Soc 122 2000 6145 6150
134. A.C. Lin, Y. Chiang, D.B. Dahlberg, and A.J. Kresge J Am Chem Soc 105 1983 5380 5386
135. J.L. Kurz, and D.N. Wexler J Am Chem Soc 97 1975 2255 2258
136. A.J. Ihde The Development of Modern Chemistry 1964 Harper & Row New York 124 139
137. J.J. Berzelius Larbok i Kemien 1818 Karolinsska Institute Stockholm
138. H. Davy Philos Trans R Soc 98 1808 1 44
139. J.B.A. Dumas C R Acad Sci 9 1839 813 815
140. H. Silberstein Ber Dtsch Chem Ges 17 1884 2660 2665
141. H. Goldschmidt, and R. Bräuer Ber Dtsch Chem Ges 39 1906 109 112
142. P.J. Paulsen, and W.D. Cooke Anal Chem 35 1963 1560
143. R. Kluger J Org Chem 29 1964 2045 2046
144. D.S. Kemp, and K.G. Paul J Am Chem Soc 97 1975 7305 7312
145. D.S. Kemp, D.D. Cox, and K.G. Paul J Am Chem Soc 97 1975 7312 7318
146. J. Gao J Am Chem Soc 117 1995 8600 8607
147. M. Drees, M. Cokoja, and F. Kühn ChemCatChem 4 2012 1703 1712
148. C.S. Yeung, and V.M. Dong J Am Chem Soc 130 2008 7826 7827
149. X. Yin, and J.R. Moss Coord Chem Rev 181 1999 27 59
150. G.A. Olah, B. Török, and J.P. Joschek J Am Chem Soc 124 2002 11379 11391