Heteroarylcarbenes

Chemical Reviews

Volumn 113, Issue 9, 2013, Pages 7179-7208

  Sheridan, Robert S ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; DIAZO COMPOUNDS; LASER FLASH PHOTOLYSIS; LOW TEMPERATURES; SINGLET STATE; SIX-MEMBERED RINGS;

CHLORINE COMPOUNDS; ELECTRONIC STRUCTURE;

ORGANIC COMPOUNDS;

EID: 84884252466     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr400150a     Document Type: Review

References (153)

1. Kirmse, W. Carbene Chemistry; Academic Press: New York, 1971.
2. Carbenes; Jones, M. and Moss, R. A., Eds.; Wiley Interscience: NewYork, 1973 and 1975; Vols. 1 and 2.
3. Carbene (Carbenoid) in Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; George Thieme Verlag: Stuttgart, 1989; Vol. E19b.
4. Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Greenwich, 1994; Vol. 1; JAI Press: Stamford, 1998; Vol. 2; Elsevier: Amsterdam, 2001; Vol. 3.
5. Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Media/Marcell Dekker: Lausanne/New York, 2002.
6. Jones, M., Jr. and Moss, R. S. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., and Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 273.
7. Tomioka, H. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., and Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 375.
8. Bertrand, G. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., and Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 329.
9. Peters, K. S. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 37.
10. Platz, M. S. Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 143.
11. Moss, R. A. and Turro, N. J. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 213.
12. Bowling, N. P.; Halter, R. J.; Hodges, J. A.; Seburg, R. A.; Thomas, P. S.; Simmons, C. S.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 2006, 128, 3291
13. Smith, I. W. M. Chem. Rev. 2003, 103, 4549
14. Merle, J. K.; Hadad, C. M In Reviews of Reactive Intermediate Chemistry, Platz, M. S.; Moss, R. A.;; Jones, M., Jr., Eds.; Wiley: New York, 2007; p 247.
15. Hatanaka, Y.; Sadakane, Y. Curr. Top. Med. Chem. 2002, 2, 271
16. Hashimoto, M.; Hatanaka, Y. Eur. J. Org. Chem. 2008, 2513
17. Blencowe, A.; Hayes, W. Soft Matter 2005, 1, 178
18. Bayley, H.; Knowles, J. R. Methods Enzymol. 1977, 46, 69
19. Fleming, S. A. Tetrahedron 1995, 51, 12479
20. See also, for application of photoaffinity labels in materials research: Mehenni, H.; Pourcelle, V.; Gohy, J.-F.; Marchand-Brynaert, J. Aust. J. Chem. 2012, 65, 193
21. Trozzolo, A. M.; Wasserman, E. In Carbenes; Jones, M.; Moss, R. A., Eds.; Wiley Interscience: New York, 1975; Vol. 2; p 185.
22. Wentrup, C. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980; p 263.
23. Wentrup, C. Top. Curr. Chem. 1976, 82, 173
24. Schuster, G. B. Adv. Phys. Org. Chem. 1986, 22, 311
25. Moss, R. A.; Jones, M., Jr. Reactive Intermediates; Wiley: New York, 1985; Vol. 3, p 91.
26. Jones, W. M. In Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic: New York, 1980; Vol. 1, Chapter 3.
27. Tomioka, H. Acc. Chem. Res. 1997, 30, 315
28. Tomioka, H. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, 1998; Vol. 2, p 175.
29. Tomioka, H. In Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Fontis Media/Marcell Dekker: Lausanne/New York, 2002; p 103.
30. Hirai, K.; Itoh, T.; Tomioka, H. Chem. Rev. 2009, 109, 3275
31. Platz, M. S. In Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Media/Marcell Dekker: Lausanne/New York, 2002; p 27.
32. Bettinger, H. F.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. In The Encyclopedia of Computational Chemistry; Schleyer, P. v. R.; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer, H. F.; Schreiner, P. R., Eds.; John Wiley & Sons: Chichester, England, 1998; p 183.
33. Woodcock, H. L.; Moran, D.; Brooks, B. R.; Schleyer, P. V. R.; Schaefer, H. F. J. Am. Chem. Soc. 2007, 129, 3763
34. Gronert, S.; Keeffe, J. R.; More O'Ferrall, R. J. Am. Chem. Soc. 2011, 133, 3381 and references therein.
35. Chu, C.-H. Chem. Phys. Lett. 1999, 309, 81 and references therein.
36. Tao, C.; Mukarakate, C.; Judge, R. H.; Reid, S. A J. Chem. Phys. 2008, 128, 171101
37. Geise, C.; Hadad, C. J. Org. Chem. 2000, 65, 8348
38. Platz, M. S.; Maloney, V. M. M. In Kinetics and Spectroscopy of Carbene and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990; p 239.
39. Scaiano, J. C. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 847.
40. Hilinski, E. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 873.
41. Baldwin, J. E. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 899.
42. Platz, M. S. In Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Media/Marcell Dekker: Lausanne/New York, 2002; p 27.
43. Merrer, D.; Moss, R. A. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Elsevier: Amsterdam, 2001; Vol. 3; p 53.
44. Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, 1998; Vol. 2; p 89.
45. Sheridan, R. S. J. Phys. Org. Chem. 2010, 23, 326
46. Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 993, 93, 1583
47. Sander, W. In Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Media/Marcell Dekker: Lausanne/New York, 2002; p 1.
48. Bally, T. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 797.
49. Matzinger, S.; Bally, T. J. Phys. Chem. A 2000, 104, 3544
50. Pliego, J. R.; De Almeida, W. B.; Celebi, S.; Zhu, Z.; Platz, M. S. J. Phys.Chem. A 1999, 103, 7481
51. Zuev, P. S.; Sheridan, R. S. J. Org. Chem. 1994, 59, 2267
52. Moss, R. A. In Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Media/Marcell Dekker: Lausanne/New York, 2002; p 57.
53. Eistert, B.; Kurze, W.; Müller, G. W. Liebigs Ann. Chem 1970, 732, 1
54. Smith, R. A. G.; Knowles, J. R. J. Chem. Soc. Perkin Trans. 2 1970, 686
55. Standring, D. N.; Knowles, J. R. Biochemistry 1980, 19, 2811
56. Baird, M. S.; Bruce, M. S. J. Chem. Res. 1989, 374
57. Baird and Bruce also hold a US Patent on various heteroarylcarbenes: U.S. Patent US 5,120,861, 1992.
58. Bonneau, R.; Liu, M. T. H.; Lapouyade, R. J. Chem. Soc. Perkin Trans. 1 1989, 1547
59. Moss, R. A.; Jang, E. G.; Kim, H.-R.; Ho, G.-J.; Baird, M. S. Tetrahedron Lett. 1992, 33, 1427
60. Romashin, Y. N.; Liu, M. T. H.; Moss, R. A. Tetrahedron Lett. 1999, 40, 7163
61. Moya-Barrios, R.; Cozens, F. L.; Schepp, N. P. J. Org. Chem. 2009, 74, 1148
62. Moya-Barrios, R.; Fregeau, B. M.; Cozens, F. L. J. Org. Chem. 2009, 74, 9126
63. Itoh, T.; Takada, A.; Hirai, K.; Tomioka, H. Org. Lett. 2005, 7, 811
64. For an extensive review, see: Koga, N.; Iwamura, H. In Carbene Chemistry-From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Media/Marcell Dekker: Lausanne/New York, 2002; p 271.
65. Li, Y.; Schuster, G. B. J. Org. Chem. 1986, 51, 4460
66. Li, Y.; Schuster, G. B. J. Org. Chem. 1987, 52, 4460
67. Li, Y. Z.; Schuster, G. B. J. Org. Chem. 1987, 52, 3975
68. Omima, S. M.; Dürr, H.; Ismail, M. T.; Abdel-Wahaba, A. A. Tetrahedron Lett. 1989, 30, 1935
69. Abdel-Wahaba, A. A.; Ismail, M. T.; Omima, S. M.; Dürr, H.; Ma, Y. Liebigs Ann 1997, 1611
70. Grasse, P. B.; Brauer, B.-E.; Zupancic, J. J.; Kaufmann, K. J.; Schuster, G. B. J. Am. Chem. Soc. 1983, 105, 6833
71. Griller, D.; Hadel, L.; Nazran, A. S.; Platz, M. S.; Wong, P. C.; Savino, T. G.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 2227
72. Nadipuram, A. K.; David, W. M.; Kumar, D.; Kerwin, S. M. Org. Lett. 2002, 4, 4543
73. Kerwin, S. M.; Nadipuram, A. K. Syn. Lett 2004, 8, 1404
74. Nadipuram, A. K.; Kerwin, S. M. Tetrahedron 2006, 62, 3798
75. Nadipuram, A. K.; Kerwin, S. M. Tetrahedron Lett. 2006, 47, 353
76. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance; McGraw-Hill: New York, 1972.
77. Wasserman, E.; Snyder, L. C.; Yager, W. A. J. Chem. Phys. 1964, 41, 1763
78. Dougherty, D. A. Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; p 117.
79. Berson, J. A. In The Chemistry of the Quinonoid Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley, New York, 1988; Vol. II.
80. McMahon, R. J.; Abelt, C. J.; Chapman, O. L.; Johnson, J. W.; Kreil, C. L.; LeRoux, J.-P.; Mooring, A. M.; West, P. R. J. Am. Chem. Soc. 1987, 109, 2456
81. Chapman, O. L.; Sheridan, R. S.; LeRoux, J. P. J. Am. Chem. Soc. 1979, 101, 3690
82. Sander, W.; Grote, D.; Kossmann, S.; Neese, F. J. Am. Chem. Soc. 2008, 130, 4396
83. Grote, D.; Finke, C.; Kossmann, S.; Neese, F.; Sander, W. Chem.-Eur. J. 2010, 16, 4496
84. Hutton, R. S.; Roth, H. D.; Schilling, M. L. M.; Suggs, W. L. J. Am. Chem. Soc. 1981, 103, 5147
85. Hutton, R. S.; Roth, H. D. J. Am. Chem. Soc. 1982, 104, 7395
86. For a review, see: Roth, H. D.; Hutton, R. S. Tetrahedron 1985, 41, 1567
87. McLachlan, A. D. Mol. Phys. 1960, 3, 233
88. Devolder, P. Tetrahedron 1979, 35, 1307
89. Kvaskoff, D.; Bednarek, P.; George, L.; Pankajakshan, S.; Wentrup, C. J. Org. Chem. 2005, 70, 7947
90. Kvaskoff, D.; Mitschke, U.; Addicott, C.; Finnerty, J.; Bednarek, P.; Wentrup, C. Aust. J. Chem. 2009, 62, 275
91. Kvaskoff, D.; Bednarek, P.; Wentrup J. Org. Chem. 2010, 75, 1600
92. Addicott, C.; Lüerssen, H.; Kuzaj, M.; Kvaskoff, D.; Wentrup, C. J. Phys. Org. Chem. 2011, 24, 999
93. Wentrup, C. Chem. Commun. 1969, 1386
94. Crow, W. D.; Wentrup, C. Tetrahedron Lett. 1968, 6149
95. Jones, W. M.;; Brinker, U. H. In Pericyclic Reactions; Marchand, A. P.,; Lehr, R. E., Eds.; Academic Press: New York, 1977; p 110
96. Gritsan, N. P.; Platz, M. S. Adv. Phys. Org. Chem. 2001, 36, 255
97. Wentrup, C. Acc. Chem. Res. 2011, 44, 393
98. Chapman, O. L.; LeRoux, J.-P. J. Am. Chem. Soc. 1978, 100, 282
99. Chapman, O. L.; Sheridan, R. S. J. Am. Chem. Soc. 1979, 101, 3690
100. Kuzaj, M.; Luerssen, H.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 480
101. Karney, W. L.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 1378
102. Kemnitz, C. R.; Karney, W. L.; Borden, W. T. J. Am. Chem. Soc. 1998, 120, 3499
103. Karney, W. L.; Borden, W. T. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, 2001; Vol. 3, p 205.
104. Amani, J.; Musavi, S. M.; Riazikia, M. Tetrahedron 2012, 68, 2067
105. Bednarek, P.; Wentrup, C. J. Am. Chem. Soc. 2003, 125, 9083
106. Lan, N. M.; Burgard, R.; Wentrup, C. J. Org. Chem. 2004, 69, 2033
107. Shirtcliff, L. D.; McClintock, S. P.; Haley, M. M. Chem. Soc. Rev. 2008, 37, 343
108. Hoffman, R. V; Shechter, H. J. Am. Chem. Soc. 1971, 93, 5940
109. Hoffman, R. V; Orphanides, G. G.; Shechter, H. J. Am. Chem. Soc. 1978, 100, 7927
110. Hoffman, R. V; Shechter, H. J. Am. Chem. Soc. 1978, 100, 7934
111. Saito, K.; Ishihara, H.; Murase, T.; Horie, Y.; Maekawa, E. Bull. Chem. Soc. Jpn. 1987, 60, 4317
112. Baird, M. S.; Bruce, I. J. Chem. Res., Synop. 1990, 134
113. Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 1998, 120, 233
114. Moss, R. A.; Fu, X.; Ma, Y.; Sauers, R. R. Tetrahedron Lett. 2003, 44, 773
115. Sparrapan, R.; Kascheres, C.; Gambardella, M. T. P. J. Org. Chem. 1995, 60, 3975
116. Hayashi, S.-I.; Nair, M.; Houser, D. J.; Shechter, H. Tetrahedron Lett. 1979, 2961
117. Nakatani, K.; Maekawa, S.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1995, 117, 10635
118. Nakatani, K.; Tanabe, K.; Saito, I. Tetrahedron Lett. 1997, 38, 1207
119. Nakatani, K.; Adachi, K.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1999, 121, 8221
120. Casey, C. P.; Strotman, N. A.; Guzei, I. A. Bielstein J. Org. Chem. 2005, 1, 18
121. Zhang, H.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2008, 10, 3591
122. Feng, L.; S. M. Kerwin, S. M. Tetrahedron Lett. 2003, 44, 3463
123. Lahoz, I. R.; Sicre, C.; Navarro-Vazquez, A.; Silva Lopez, C.; Cid, M.-M. Org. Lett. 2009, 11, 4802
124. Lahoz, I. R.; Lopez, C. S.; Navarro-Vazquez, A.; Cid, M.-M. J. Org. Chem. 2011, 76, 3266
125. Geuenich, D.; Hess, K.; Köhler, F.; Herges, R. Chem. Rev. 2005, 105, 3758
126. Frey, L. F.; Tillyer, R. D.; Ouellet, S. G.; Reamer, R. A.; Grabowski, E. J. J.; Reider, P. R. J. Am. Chem. Soc. 2000, 122, 1215
127. Kimball, D. B.; Weakley, T. J. R.; Haley, M. M. J. Org. Chem. 2002, 67, 6395
128. Kimball, D. B.; Hayes, A. G.; Haley, M. M. Org. Lett. 2000, 2, 3825
129. Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572
130. Shirtcliff, L. D.; Weakley, T. J. R.; Haley, M. M.; Herges, R.; Kohler, F. J. Org. Chem. 2004, 69, 6979
131. See, for example: Young, B. S.; Köhler, F.; Herges, R.; Haley, M. M. J. Org. Chem. 2011, 76, 8483
132. Albers, R.; Sander, W. Liebigs Ann./Recl. 1997, 897
133. Pharr, C. R.; Kopff, L.; Bennett, B.; Reid, S.; McMahon, R. J. J. Am. Chem. Soc. 2012, 134, 6443
134. Sander, W.; Albers, R.; Komnick, P.; Wandel, H. Liebigs Ann./Recl. 1997, 901
135. Röser, C.; Albers, R.; Sander, W. Eur. J. Org. Chem. 2001, 269
136. Khasanova, T.; Sheridan, R. S. J. Am. Chem. Soc. 2000, 122, 8585
137. Nikitina, A. F.; Sheridan, R. S. Org. Lett. 2005, 7, 4467
138. Wang, J.; Sheridan, R. S. Org. Lett. 2007, 9, 3177
139. Nikitina, A.; Sheridan, R. S. J. Am. Chem. Soc. 2002, 124, 7670
140. Baird, M. S.; Bruce, I. J. Chem. Res., Synop. 1989, 376
141. Pan, W.; Balci, M.; Shevlin, P. B. J. Am. Chem. Soc. 1997, 119, 5035
142. McKee, M. L.; Shevlin, P. B.; Zottola, M. J. Am. Chem. Soc. 2001, 123, 9418
143. Albers, R.; Sander, W. J. Org. Chem. 1997, 62, 761
144. Khasanova, T.; Sheridan, R. S. Org. Lett. 1999, 1, 1091
145. Herges, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 255
146. See also: Herges, R. J. Chem. Inf. Comput. Sci. 1994, 34, 91
147. Sun, Y.; Wong, M. W. J. Org. Chem. 1999, 64, 9170
148. Birney, D. M. J. Am. Chem. Soc. 2000, 122, 10917
149. McClintock, S. P.; Shirtcliff, L. D.; Herges, R.; Haley, M. M. J. Org. Chem. 2008, 73, 8755
150. Sander, W.; Bucher, G.; Reichel, F.; Cremer, D. J. Am. Chem. Soc. 1991, 113, 5311
151. Kreil, C. L. Ph.D. Dissertation, University of California, Los Angeles, 1983.
152. Zhang, J. Ph.D. Dissertation, University of Nevada, Reno, 2004.
153. Ghimire, R. Ph.D. Dissertation, University of Nevada, Reno, 2012.