Stereoelectronic parameters associated with N-heterocyclic carbene (NHC) ligands: A quest for understanding

Coordination Chemistry Reviews

Volumn 251, Issue 5-6, 2007, Pages 874-883

  Díez González, Silvia ^a   Nolan, Steven P ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

Catalysis; Metal ligand bond; N Heterocyclic carbenes; Stereoelectronic; Transition metals

Indexed keywords

EID: 33846797894     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.10.004     Document Type: Review

References (140)

1. Wanzlick H.W., and Kleiner H.J. Angew. Chem. 73 (1961) 493
2. Wanzlick H.W. Angew. Chem. 74 (1962) 129
3. Wanzlick H.W., Esser F., and Kleiner H.J. Chem. Ber. 96 (1963) 1208
4. Wanzlick H.W., and Kleiner H.J. Chem. Ber. 96 (1963) 3024
5. Fischer E.O., and Maasböl A. Angew. Chem., Int. Ed. Engl. 3 (1964) 580
6. Schrock R.R. J. Am. Chem. Soc. 96 (1974) 6796
7. Wanzlick H.W., and Schönherr H.-J. Angew. Chem., Int. Ed. Engl. 7 (1968) 141
8. Öfele K. J. Organomet. Chem. 12 (1968) P42
9. Öfele K. Angew. Chem., Int. Ed. Engl. 9 (1970) 739
10. Öfele K. J. Organomet. Chem. 22 (1970) C9
11. Igau A., Grutzmacher H., Baceiredo A., and Bertrand G. J. Am. Chem. Soc. 110 (1988) 6463
12. Arduengo III A.J., Harlow R.L., and Kline M.A. J. Am. Chem. Soc. 113 (1991) 361
13. Tolman C.A. Chem. Rev. 77 (1977) 313
14. Green J.C., Scur R.G., Arnold P.L., and Cloke G.N. Chem. Commun. (1997) 1963
15. Herrmann W.A. Angew. Chem. Int. Ed. 41 (2002) 1290
16. Perry M.C., and Burgess K. Tetrahedron: Assymetry 14 (2003) 951
17. Peris E., and Crabtree R.H. Coord. Chem. Rev. 248 (2004) 2239
18. Crudden C.M., and Allen D.P. Coord. Chem. Rev. 248 (2004) 2247
19. César V., Bellemin-Laponnaz S., and Gade L.H. Chem. Soc. Rev. 33 (2004) 619
20. Díez-González S., and Nolan S.P. Annu. Rep. Prog. Chem., Sect. B 101 (2005) 171
21. Cavallo L., Correa A., Costabile C., and Jacobsen H. J. Organomet. Chem. 690 (2005) 5407
22. Teuma E., Lyon-Saunier C., Gornitzka H., Mignani G., Baceiredo A., and Bertrand G. J. Organomet. Chem. 690 (2005) 5541
23. Alder R.W., Allen P.R., Murray M., and Orpen A. Angew. Chem., Int. Ed. Engl. 35 (1996) 1121
24. Alder R.W., and Blake M.E. Chem. Commun. (1997) 1513
25. Alder R.W., Blake M.E., Chaker I., Harvey J.N., Paolini F., and Schutz J. Angew. Chem. Int. Ed. 43 (2004) 5896
26. Herrmann W.A., Öfele K., Preysing D.V., and Herdtweck E. J. Organomet. Chem. 684 (2003) 235
27. Recently Bertrand showed that the presence of a tertiary carbon center next to the carbene center allowed for the isolation of stable carbenes that could coordinate transition metals:. Lavallo V., Canac Y., Präsan g C., Donnadieu B., and Bertrand G. Angew. Chem. Int. Ed. 44 (2005) 5705
28. Lavallo V., Canac Y., DeHope A., Donnadieu B., and Bertrand G. Angew. Chem. Int. Ed. 44 (2005) 7236
29. Dixon D.A., and Arduengo III A.J. J. Phys. Chem. 95 (1991) 4180
30. Cioslowski J. Int. J. Quantum Chem., Quantum Chem. Symp. 27 (1993) 309
31. Arduengo III A.J., Bock H., Chen H., Denk M., Dixon D.A., Green J.C., Herrmann W.A., Jones N.L., Wagner M., and West R. J. Am. Chem. Soc. 116 (1994) 6641
32. Arduengo III A.J., Dias H.V.R., Dixon D.A., Harlow R.L., Klooster W.T., and Koetzle T.F. J. Am. Chem. Soc. 116 (1994) 6812
33. Arduengo III A.J., Dias H.V.R., Harlow R.L., and Kline M. J. Am. Chem. Soc. 114 (1992) 5530
34. Heinemann C., Müller T., Apeloig Y., and Schwarz H. J. Am. Chem. Soc. 118 (1996) 2023
35. Boehme C., and Frenking G. J. Am. Chem. Soc. 118 (1996) 2039
36. Lehmann J.F., Urquhart S.G., Ennios L.E., Hitchcock A.P., Hatano K., Gupta S., and Denk M.K. Organometallics 18 (1999) 1862
37. Minkin V.I., Glukhovtsev M.N., and Simkin B.Y. Aromacity and Antiaromacity (1994), J. Wiley & Sons, New York
38. Wanzlick H.W. Angew. Chem., Int. Ed. Engl. 1 (1962) 75
39. Schönberr H.-J., and Wanzlick H.-W. Chem. Ber. 103 (1970) 1037
40. Arduengo III A.J., Goerlich J.R., and Marshall W.J. J. Am. Chem. Soc. 117 (1995) 11027
41. Huang J., Stevens E.D., Nolan S.P., and Petersen J.L. J. Am. Chem. Soc. 121 (1999) 2674
42. Scholl M., Trnka T.M., Morgan J.P., and Grubbs R.H. Tetrahedron Lett. 40 (1999) 2247
43. Jafarpour L., and Nolan S.P. Organometallics 19 (2000) 2055
44. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
45. Schrock R.R., Murdzeck J., Bazan G.C., Robbins J., DiMare M., and O'Regan M. J. Am. Chem. Soc. 112 (1990) 3875
46. Schwab P., France M.B., and Ziller J.W. Angew. Chem., Int. Ed. Engl. 34 (1995) 2039
47. Schwab P., Grubbs R.H., and Ziller R.H. J. Am. Chem. Soc. 118 (1996) 100
48. Huang J., Schanz H.-J., Stevens E.D., and Nolan S.P. Organometallics 18 (1999) 2370
49. Luo L., and Nolan S.P. Organometallics 13 (1994) 4781
50. Reactions were suitable for calorimetric investigations since they proceeded rapidly and quantitatively as monitored by NMR spectroscopy.
51. Hillier A.C., Sommer W.J., Yong B.S., Petersen J.L., Cavallo L., and Nolan S.P. Organometallics 22 (2003) 4322
52. Dias E.L., Nguyen S.T., and Grubbs R.H. J. Am. Chem. Soc. 119 (1997) 3887
53. Ullman M., and Grubbs R.H. Organometallics 17 (1998) 2484
54. Adlhart C., Hinderling C., Baumann H., and Chen P. J. Am. Chem. Soc. 122 (2000) 8204
55. Adlhart C., Volland M.A.O., Hofmann P., and Chen P. Helv. Chim. Acta 83 (2000) 2192
56. Adlhart C., and Chen P. Helv. Chim. Acta 83 (2000) 3306
57. Cavallo L. J. Am. Chem. Soc. 124 (2002) 8965
58. Adlhart C., and Chen P. J. Am. Chem. Soc. 126 (2004) 3496
59. b.
60. Alder R.W., Allen P.R., and Williams S.J. J. Chem. Soc., Chem. Commun. (1995) 1267
61. Kim Y.-J., and Streitwieser A. J. Am. Chem. Soc. 124 (2002) 5757 For a study on the basicity of phosphino(silyl)carbenes see: D. Martin, O. Illa, A. Baceiredo, G. Bertrand, R.M. Ortuño, V. Branchadell, J. Org. Chem. 70 (2005) 5671-5677
62. Magill A.M., Cavell K.J., and Yates B.F. J. Am. Chem. Soc. 126 (2004) 8717
63. Alder R.W., Allen P.R., Murray M., and Orpen A.G. Angew. Chem., Int. Ed. Engl. 35 (1996) 1121
64. Denk K., Sirsch P., and Herrmann W.A. J. Organomet. Chem. 649 (2002) 219
65. Rahman M.M., Liu H.-Y., Eriks K., Prock A., and Giering W.P. Organometallics 8 (1989) 1
66. For representative examples see:. Milne J.E., and Buchwald S.L. J. Am. Chem. Soc. 126 (2004) 13028
67. Shen Q., Shekhar S., Stambuli J.P., and Hartwig J.F. Angew. Chem. Int. Ed. 44 (2005) 1371
68. Huang J., Stevens E.D., and Nolan S.P. Organometallics 19 (2000) 1194
69. Perrin L., Clot E., Eisenstein O., Loch J., and Crabtree R.H. Inorg. Chem. 40 (2001) 5806
70. Chianese A.R., Li X., Jarzen M.C., Faller J.W., and Crabtree R.H. Organometallics 22 (2003) 1663
71. Öfele K., Herrmann W.A., Mihalios D., Elison M., Herdtweck E., Scherer W., and Mink J. J. Organomet. Chem. 459 (1993) 177
72. Herrmann W.A., Goossen L.J., Artus G.R.J., and Köcher C. Organometallics 16 (1997) 2472
73. Dorta R., Stevens E.D., Hoff C.D., and Nolan S.P. J. Am. Chem. Soc. 125 (2003) 10490
74. Dorta R., Stevens E.D., Scott N.M., Costabile C., Cavallo L., Hoff C.D., and Nolan S.P. J. Am. Chem. Soc. 127 (2005) 2485
75. Tolman C.A. J. Am. Chem. Soc. 92 (1970) 2953
76. Chianese A.R., Kovacevic A., Zeglis B.M., Faller J.W., and Crabtree R.H. Organometallics 23 (2004) 2461
77. Petz W., Weller F., Uddin J., and Frenking G. Organometallics 18 (1999) 619
78. Krahulic K.E., Enright G.D., Parvez M., and Roesler R. J. Am. Chem. Soc. 127 (2005) 4142
79. Präsang C., Donnadieu B., and Bertrand G. J. Am. Chem. Soc. 127 (2005) 10182
80. Arduengo III A.J., and Krafczyk R. Chem Z. 32 (1998) 6
81. Huang J., Haar C.M., Nolan S.P., Marshall W.J., and Moloy K.G. J. Am. Chem. Soc. 120 (1998) 7806
82. Clement N.D., Cavell K.J., Jones C., and Elseiver C.J. Angew. Chem. Int. Ed. 43 (2004) 1277
83. Schaub T., and Radius U. Chem. Eur. J. 11 (2005) 5024
84. Viciu M.S., Navarro O., Germaneau R.F., Kelly III R.A., Sommer W., Marion N., Stevens E.D., Cavallo L., and Nolan S.P. Organometallics 23 (2004) 1629
85. Marion N., Navarro O., Mei J., Stevens E.D., Scott N.M., and Nolan S.P. J. Am. Chem. Soc. 128 (2006) 4101
86. Simms R.W., Drewitt M.J., and Baird M.C. Organometallics 21 (2002) 2958
87. Chen A.C., Ren L., Decken A., and Crudden C.M. Organometallics 19 (2000) 3459
88. Allen D.P., Crudden C.M., Calhoun L.A., and Wang R. J. Organomet. Chem. 689 (2004) 3203
89. See also:. Lebel H., Janes M.K., Charette A.B., and Nolan S.P. J. Am. Chem. Soc. 126 (2004) 5046
90. Öfele K., and Kreiter C.G. Chem. Ber. 105 (1972) 529
91. Öfele K., and Herberhold M. Z. Naturforsch. 28 (1973) 306
92. Tafipolsky M., Scherer W., Öfele K., Artus G., Pedersen B., Herrmann W.A., and McGrady G.S. J. Am. Chem. Soc. 124 (2002) 5865
93. Frison G., and Sevin A. J. Chem. Soc., Perkin Trans. 2 (2002) 1692
94. Arduengo III A.J., Dias H.V.R., Davidson F., and Harlow R.L. J. Organomet. Chem. 462 (1993) 13
95. Schumann H., Gottfriedsen J., Glanz M., Dechert S., and Demtschuk J. J. Organomet. Chem. 617-618 (2001) 588
96. Kuhn N., Henkel G., Kratz T., Kreutzberg J., Boese R., and Maulitz A.H. Chem. Ber. 126 (1993) 2041
97. Wacker A., Pritzkow H., and Siebert W. Eur. J. Inorg. Chem. (1998) 843
98. Arduengo III A.J., Dias H.V.R., Calabrese J.C., and Davidson F. J. Am. Chem. Soc. 114 (1992) 9724
99. Li X.-W., Su J., and Robinson G.H. Chem. Commun. (1996) 2683
100. Nakai H., Tang Y.J., Gantzel P., and Meyer K. Chem. Commun. (2003) 24
101. Kuhn N., Kratz T., Bläser D., and Boese R. Chem. Ber. 128 (1995) 245
102. Schäfer A., Weidenbruch M., Saak W., and Pohl S. J. Chem. Soc., Chem. Commun. (1995) 1157
103. Boesveld W.M., Gehrhus B., Hitchcock P.B., Lappert M.F., and von R. Scheleyer P. Chem. Commun. (1999) 755
104. Arduengo III A.J., Tamm M., McLain S.J., Calabrese C.J., Davidson F., and Marshall W.J. J. Am. Chem. Soc. 116 (1994) 7927
105. Schumann H., Glanz M., Winterfeld J., Hemling H., Kuhn N., and Kratz T. Angew. Chem., Int. Ed. Engl. 33 (1994) 1733
106. Fischer R.D. Angew. Chem., Int. Ed. Engl. 33 (1994) 2165
107. Schumann H., Glanz M., Gottfriedsen J., Dechert S., and Wolff D. Pure Appl. Chem. 73 (2001) 279
108. Arduengo III A.J., Davidson F., Krafczyk R., Marshall W.J., and Tamm M. Organometallics 17 (1998) 3375
109. Mungur S.A., Liddle S.T., Wilson C., Sarsfield M.J., and Arnold P.L. Chem. Commun. (2004) 2738
110. Fenton D.E. In: Wilkinson G., Gillard R.D., and McCleverty J.A. (Eds). Comprehensive Coordination Chemistry (1987), Pergamon, Oxford (chapter 23)
111. Herrmann W.A., Runte O., and Artus G. J. Organomet. Chem. 501 (1995) C1
112. Fröhlich N., Pidun U., Stahl M., and Frenking G. Organometallics 16 (1997) 442
113. Herrmann W.A., Gerstberger G., and Spiegler M. Organometallics 16 (1997) 2209
114. Green J.C., Scurr R.G., Arnold P.L., and Cloke F.G.N. Chem. Commun. (1997) 1963
115. Boehme C., and Frenking G. Organometallics 17 (1998) 5801
116. Niehues M., Erker G., Kehr G., Schwab P., and Fröhlich R. Organometallics 21 (2002) 2905
117. Lee M.-T., and Hu C.-H. Organometallics 23 (2004) 976
118. Saravanakumar S., Kindermann M.K., Heinicke J., and Köckerling M. Chem. Commun. (2006) 640
119. For selected reports, see:. Arduengo III A.J., Gamper S.F., Calabrese J.C., and Davidson F. J. Am. Chem. Soc. 116 (1994) 4391
120. Boehme C., and Frenking G. Organometallics 17 (1998) 5801
121. Gérard H., Clot E., and Eisenstein O. New. J. Chem. 23 (1999) 495
122. Huang J., Schanz H.-J., Stevens E.D., and Nolan S.P. Inorg. Chem. 39 (2000) 1042
123. McGuinness D.S., Saendig N., Yates B.F., and Cavell K.J. J. Am. Chem. Soc. 123 (2001) 4029
124. Jazzar R.F.R., Macgregor S.A., Mahon M.F., Richards S.P., and Whittlesey M.K. J. Am. Chem. Soc. 124 (2002) 4944
125. Deuvel D.V. Organometallics 21 (2002) 4303
126. Termaten A.T., Schakel M., Ehlers A.W., Lutz M., Spek A.L., and Lammertsma K. Chem. Eur. J. 9 (2003) 3577
127. Sübner M., and Plenio H. Chem. Commun. (2005) 5417
128. Clarke M.J., and Taube H. J. Am. Chem. Soc. 97 (1975) 1397
129. Abernethy C.D., Codd G.M., Spicer M.D., and Taylor M.K. J. Am. Chem. Soc. 125 (2003) 1128
130. Kapp J., Schade C., El-Nahasa A.M., and von R. Schleyer P. Angew. Chem., Int. Ed. Engl. 35 (1996) 2236
131. Shukla P., Johnson J.A., Vidovic D., Cowley A.H., and Abernethy C.D. Chem. Commun. (2004) 360
132. Garrison J.C., Simons R.S., Kofron W.G., Tessier C.A., and Youngs W.J. Chem. Commun. (2001) 1780
133. Tulloch A.A.D., Danopoulos A.A., Kleinhenz S., Light M.E., Hursthouse M.B., and Eastham G. Organometallics 20 (2001) 2027
134. Hu X., Tang Y., Gantzel P., and Meyer K. Organometallics 22 (2003) 612
135. Nemcsok D., Wichmann K., and Frenking G. Organometallics 23 (2004) 3640
136. Lein M., Szabó A., Kovács A., and Frenking G. Faraday Discuss. 124 (2003) 365
137. Oldham W.J., Oldham S.M., Scott B.L., Abney K.D., Smith W.H., and Costa D.A. Chem. Commun. (2001) 1348
138. Nakai H., Hu X., Zakharov L.N., Rheingold A.L., and Meyer K. Inorg. Chem. 43 (2004) 855
139. Dorta R., Stevens E.D., and Nolan S.P. J. Am. Chem. Soc. 126 (2004) 5054
140. Scott N.M., Dorta R., Stevens E.D., Correa A., Cavallo L., and Nolan S.P. J. Am. Chem. Soc. 127 (2005) 3516