Erratum to "Understanding the M-(NHC) (NHC = N-heterocyclic carbene) bond" [Coordin. Chem. Rev. 253 (2009) 687-703] (DOI:10.1016/j.ccr.2008.06.006);Understanding the M‒(NHC) (NHC = N-heterocyclic carbene) bond

Coordination Chemistry Reviews

Volumn 253, Issue 5-6, 2009, Pages 687-703

  Jacobsen, Heiko ^a   Correa, Andrea ^b   Poater, Albert ^b   Costabile, Chiara ^b   Cavallo, Luigi ^b  

^a KemKom   (United States)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

DFT methods; M single bond ligand bond; N heterocyclic carbenes; Transition metals

Indexed keywords

EID: 60649120416     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2009.04.007     Document Type: Erratum

References (168)

1. Wanzlick H.W., and Kleiner H.J. Angew. Chem. 73 (1961) 493
2. Wanzlick H.-W. Angew. Chem. Int. Ed. Engl. 1 (1962) 75
3. Öfele K. J. Organomet. Chem. 12 (1968) P42
4. Wanzlick H.W., and Schönherr H.-J. Angew. Chem. Int. Ed. Engl. 7 (1968) 141
5. Öfele K., and Herberhold M. Angew. Chem. Int. Ed. Engl. 9 (1970) 739
6. Arduengo A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361
7. Arduengo A.J., Kline M., Calabrese J.C., and Davidson F. J. Am. Chem. Soc. 113 (1991) 9704
8. Arduengo A.J., Dias H.V.R., Harlow R.L., and Kline M. J. Am. Chem. Soc. 114 (1992) 5530
9. Arduengo A.J., Davidson F., Dias H.V.R., Goerlich J.R., Khasnis D., Marshall W.J., and Prakasha T.K. J. Am. Chem. Soc. 119 (1997) 12742
10. Arduengo A.J., Goerlich J.R., and Marshall W.J. J. Am. Chem. Soc. 117 (1995) 11027
11. Weskamp T., Schattenmann W.C., Spiegler M., and Herrmann W.A. Angew. Chem. Int. Ed. 37 (1998) 2490
12. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
13. Huang J., Stevens E.D., Nolan S.P., and Peterson J.L. J. Am. Chem. Soc. 121 (1999) 2674
14. Hoveyda A.H., and Schrock R.R. Chem. Eur. J. 7 (2001) 945
15. Fürstner A. Angew. Chem. Int. Ed. 39 (2000) 3012
16. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18
17. Jafarpour L., and Nolan S.P. J. Organomet. Chem. 617-618 (2001) 17
18. Vázquez-Serrano L.D., Owens B.T., and Buriak J.M. Chem. Commun. (2002) 2518
19. Lee H.M., Jiang T., Stevens E.D., and Nolan S.P. Organometallics 20 (2001) 1255
20. Hillier A.C., Lee H.M., Stevens E.D., and Nolan S.P. Organometallics 20 (2001) 4246
21. Grasa G.A., Viciu M.S., Huang J., and Nolan S.P. J. Org. Chem. 66 (2001) 7729
22. Grasa G.A., Viciu M.S., Huang J., Zhang C., Trudell M.L., and Nolan S.P. Organometallics 21 (2002) 2866
23. Marion N., Navarro O., Mei J., Stevens E.D., Scott N.M., and Nolan S.P. J. Am. Chem. Soc. 128 (2006) 4101
24. Marion N., de Frémont P., Lemière G., Stevens E.D., Fensterbank L., Malacria M., and Nolan S.P. Chem. Commun. (2006) 2048
25. Correa A., Mario N., Fensterban L., Malacria M., Nolan S.P., and Cavallo L. Angew. Chem. Int. Ed. 47 (2008) 718
26. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951
27. Funk T.W., Berlin J.M., and Grubbs R.H. J. Am. Chem. Soc. 128 (2006) 1840
28. Seiders T.J., Ward D.W., and Grubbs R.H. Org. Lett. 3 (2001) 3225
29. Van Veldhuizen J.J., Garber S.B., Kingsbury J.S., and Hoveyda A.H. J. Am. Chem. Soc. 124 (2002) 4954
30. Diez-Gonzalez S., and Nolan S.P. Coord. Chem. Rev. 251 (2007) 874
31. Glorius F. Top. Organomet. Chem. 21 (2007) 1
32. Alder R.W., Blake M.E., Chaker L., Harvey J.N., Paolini F., and Schutz J. Angew. Chem. Int. Ed. 43 (2004) 5896
33. Cavallo L., Correa A., Costabile C., and Jacobsen H. J. Organomet. Chem. 690 (2005) 5407
34. Bourissou D., Guerret O., Gabbaï F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
35. Crudden C.M., and Allen D.P. Coord. Chem. Rev. 248 (2004) 2247
36. Nair V., Bindu S., and Sreekumar V. Angew. Chem. Int. Ed. 43 (2004) 5130
37. Frenking G., Solà M., and Vyboishchikov S.F. J. Organomet. Chem. 690 (2005) 6178
38. Herrmann W.A. Angew. Chem. Int. Ed. 41 (2002) 1291
39. Heinemann C., and Thiel W. Chem. Phys. Lett. 217 (1994) 11
40. Hoffmann R. J. Am. Chem. Soc. 90 (1968) 1475
41. Su M.-D., and Chu S.-Y. Chem. Phys. Lett. 308 (1999) 283
42. Arduengo 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
43. Ullah F., Bajor G., Veszpremi T., Jones P.G., and Heinicke J.W. Angew. Chem. Int. Ed. 46 (2007) 2697
44. Heinemann C., Muller T., Apeloig Y., and Schwarz H. J. Am. Chem. Soc. 118 (1996) 2023
45. Boehme C., and Frenking G. J. Am. Chem. Soc. 118 (1996) 2039
46. In: Nolan S.P. (Ed). N-heterocyclic Carbenes in Synthesis (2006), Wiley-VCH
47. Glorius F. N-heterocyclic Carbenes in Transition Metal Catalysis (2007)
48. Arduengo A.J., Krafczyk R., Arduengo A.J., and Krafczyk R. Chem. Unserer Zeit 32 (1998) 6
49. Herrmann W.A., and Kocher C. Angew. Chem. Int. Ed. Engl. 36 (1997) 2163
50. Regitz M. Angew. Chem. Int. Ed. Engl. 35 (1996) 725
51. Carter E.A., and Goddard III W.A. J. Phys. Chem. 90 (1986) 998
52. Cheng M.J., and Hu C.H. Chem. Phys. Lett. 322 (2000) 83
53. Cheng M.J., and Hu C.H. Chem. Phys. Lett. 349 (2001) 477
54. Nyulászi L., Veszprémi T., and Forró A. Phys. Chem. Chem. Phys. 2 (2000) 3127
55. Graham D.C., Cavell K.J., and Yates B.F. J. Phys. Org. Chem. 18 (2005) 298
56. Denk M.K., Hezarkhani A., and Zheng F.L. Eur. J. Inorg. Chem. (2007) 3527
57. Poater A., Ragone F., Giudice S., Costabile C., Dorta R., Nolan S.P., and Cavallo L. Organometallics 27 (2008)
58. Tolman C.A. Chem. Rev. 77 (1977) 313
59. Liu Y.F., Lindner P.E., and Lemal D.M. J. Am. Chem. Soc. 121 (1999) 10626
60. Herrmann W.A., Kocher C., Goossen L.J., and Artus G.R.J. Chem. Eur. J. 2 (1996) 1627
61. Wiberg N. Angew. Chem. Int. Ed. Engl. 7 (1968) 766
62. Ziegler T. Chem. Rev. 91 (1991) 651
63. Hillier A.C., Sommer W.J., Yong B.S., Petersen J.L., Cavallo L., and Nolan S.P. Organometallics 22 (2003) 4322
64. Hu X.L., Castro-Rodriguez I., Olsen K., and Meyer K. Organometallics 23 (2004) 755
65. 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
66. Kelly III R.A., Clavier H., Giudice S., Scott N.M., Stevens E.D., Bordner J., Samardjiev I., Hoff C.D., Cavallo L., and Nolan S.P. Organometallics 27 (2008) 202
67. van Lenthe E., Ehlers A.E., and Baerends E.J. J. Chem. Phys. 110 (1999) 8943
68. van Lenthe E., Baerends E.J., and Snijders J.G. J. Chem. Phys. 99 (1993) 4597
69. van Lenthe E., Baerends E.J., and Snijders J.G. J. Chem. Phys. 101 (1994) 9783
70. Fantasia S., Petersen J.L., Jacobsen H., Cavallo L., and Nolan S.P. Organometallics 26 (2007) 5880
71. Green J.C., Scurr R.G., Arnold P.L., and Cloke F.G.N. Chem. Commun. (1997) 1963
72. Frison G., and Sevin A. J. Chem. Soc., Perkin Trans. 2 (2002) 1692
73. Kuhn N., Kratz T., Blaser D., and Boese R. Chem. Ber. 128 (1995) 245
74. Kuhn N., Henkel G., Kratz T., Kreutzberg J., Boese R., and Maulitz A.H. Chem. Ber. Recl. 126 (1993) 2041
75. Arduengo A.J., Dias H.V.R., Calabrese J.C., and Davidson F. J. Am. Chem. Soc. 114 (1992) 9724
76. Li X.W., Su J.R., and Robinson G.H. Chem. Commun. (1996) 2683
77. Nakai H., Tang Y.J., Gantzel P., and Meyer K. Chem. Commun. (2003) 24
78. Boesveld W.M., Gehrhus B., Hitchcock P.B., Lappert M.F., and Schleyer P.V. Chem. Commun. (1999) 755
79. Alder R.W., Blake M.E., Bortolotti C., Bufali S., Butts C.P., Linehan E., Oliva J.M., Orpen A.G., and Quayle M.J. Chem. Commun. (1999) 241
80. Arduengo A.J., Dias H.V.R., Davidson F., and Harlow R.L. J. Organomet. Chem. 462 (1993) 13
81. Arduengo A.J., Davidson F., Krafczyk R., Marshall W.J., and Tamm M. Organometallics 17 (1998) 3375
82. Schumann H., Gottfriedsen J., Glanz M., Dechert S., and Demtschuk J. J. Organomet. Chem. 617 (2001) 588
83. Schumann H., Glanz M., Winterfeld J., Hemling H., Kuhn N., and Kratz T. Angew. Chem. Int. Ed. Engl. 33 (1994) 1733
84. Schumann H., Glanz M., Gottfriedsen J., Dechert S., and Wolff D. Pure Appl. Chem. 73 (2001) 279
85. Arduengo A.J., Tamm M., McLain S.J., Calabrese J.C., Davidson F., and Marshall W.J. J. Am. Chem. Soc. 116 (1994) 7927
86. Fischer R.D. Angew. Chem. Int. Ed. Engl. 33 (1994) 2165
87. Herrmann W.A., Runte O., and Artus G. J. Organomet. Chem. 501 (1995) C1
88. Fröhlich N., Pidun U., Stahl M., and Frenking G. Organometallics 16 (1997) 442
89. Niehues M., Erker G., Kehr G., Schwab P., Fröhlich R., Blacque O., and Berke H. Organometallics 21 (2002) 2905
90. Niehues M., Kehr G., Erker G., Wibbeling B., Fröhlich R., Blacque O., and Berke H. J. Organomet. Chem. 663 (2002) 192
91. Herrmann W.A., Öfele K., Elison M., Kuhn F.E., and Roesky P.W. J. Organomet. Chem. 480 (1994) C7
92. Nikiforov G.B., Roesky H.W., Jones P.G., Magull J., rg x.f., Ringe A., and Oswald R.B. Inorg. Chem. 47 (2008) 2171
93. Lee M.T., and Hu C.H. Organometallics 23 (2004) 976
94. Arduengo A.J., Gamper S.F., Calabrese J.C., and Davidson F. J. Am. Chem. Soc. 116 (1994) 4391
95. Slater J.S. The Calculation of Molecular Orbitals (1979), Wiley
96. Penka E.F., Schlaepfer C.W., Atanasov M., Albrecht M., and Daul C. J. Organomet. Chem. 692 (2007) 5709
97. Ray L., Shaikh M.M., and Ghosh P. Dalton Trans. (2007) 4546
98. Boehme C., and Frenking G. Organometallics 17 (1998) 5801
99. Vyboishchikov S.F., and Frenking G. Chem. Eur. J. 4 (1998) 1428
100. Dapprich S., and Frenking G. J. Phys. Chem. 99 (1995) 9352
101. Schwerdtfeger P., Boyd P.D.W., Burrell A.K., Robinson W.T., and Taylor M.J. Inorg. Chem. 29 (1990) 3593
102. Pekka P. Angew. Chem. Int. Ed. 43 (2004) 4412
103. Pyykko P., and Runeberg N. Chem. Asian J. 1 (2006) 623
104. Gorin D.J., and Toste F.D. Nature 446 (2007) 395
105. Samantaray M.K., Katiyar V., Roy D., Pang K., Nanavati H., Stephen R., Sunoj R.B., and Ghosh P. Eur. J. Inorg. Chem. (2006) 2975
106. Ray L., Shaikh M.M., and Ghosh P. Inorg. Chem. 47 (2008) 230
107. Samantaray M.K., Pang K., Shaikh M.M., and Ghosh P. Inorg. Chem. 47 (2008) 4153
108. Hayes J.M., Viciano M., Peris E., Ujaque G., and Lledos A. Organometallics 26 (2007) 6170
109. Ho V.M., Watson L.A., Huffman J.C., and Caulton K.G. New J. Chem. 27 (2003) 1446
110. Garrison J.C., Simons R.S., Kofron W.G., Tessier C.A., and Youngs W.J. Chem. Commun. (2001) 1780
111. Tulloch A.A.D., Danopoulos A.A., Kleinhenz S., Light M.E., Hursthouse M.B., and Eastham G. Organometallics 20 (2001) 2027
112. Hu X.L., Tang Y.J., Gantzel P., and Meyer K. Organometallics 22 (2003) 612
113. Shukla P., Johnson J.A., Vidovic D., Cowley A.H., and Abernethy C.D. Chem. Commun. (2004) 360
114. Abernethy C.D., Codd G.M., Spicer M.D., and Taylor M.K. J. Am. Chem. Soc. 125 (2003) 1128
115. Jacobsen H., Correa A., Costabile C., and Cavallo L. J. Organomet. Chem. 691 (2006) 4350
116. Tonner R., Heydenrych G., and Frenking G. Chem. Asian J. 2 (2007) 1555
117. Tafipolsky M., Scherer W., Öfele K., Artus G., Pedersen B., Herrmann W.A., and McGrady G.S. J. Am. Chem. Soc. 124 (2002) 5865
118. Mercs L., Labat G., Neels A., Ehlers A., and Albrecht M. Organometallics 25 (2006) 5648
119. Lever A.B.P. Inorg. Chem. 30 (1991) 1980
120. Lever A.B.P. Inorg. Chem. 29 (1990) 1271
121. Sanderson M.D., Kamplain J.W., and Bielawski C.W. J. Am. Chem. Soc. 128 (2006) 16514
122. Khramov D.M., Lynch V.M., and Bielawski C.W. Organometallics 26 (2007) 6042
123. Termaten A.T., Schakel M., Ehlers A.W., Lutz M., Spek A.L., and Lammertsma K. Chem. Eur. J. 9 (2003) 3577
124. Nemcsok D., Wichmann K., and Frenking G. Organometallics 23 (2004) 3640
125. Dorta R., Stevens E.D., and Nolan S.P. J. Am. Chem. Soc. 126 (2004) 5054
126. Scott N.M., Dorta R., Stevens E.D., Correa A., Cavallo L., and Nolan S.P. J. Am. Chem. Soc. 127 (2005) 3516
127. Guerra C.F., Handgraaf J.W., Baerends E.J., and Bickelhaupt F.M. J. Comput. Chem. 25 (2004) 189
128. Jacobsen H. J. Organomet. Chem. 690 (2005) 6068
129. Samantaray M.K., Roy D., Patra A., Stephen R., Saikh M., Sunoj R.B., and Ghosh P. J. Organomet. Chem. 691 (2006) 3797
130. Gagliardi L., and Cramer C.J. Inorg. Chem. 45 (2006) 9442
131. Kausamo A., Tuononen H.M., Krahulic K.E., and Roesler R. Inorg. Chem. 47 (2008) 1145
132. Cases M., Frenking G., Duran M., and Solà M. Organometallics 21 (2002) 4182
133. Morokuma K. J. Chem. Phys. 55 (1971) 1236
134. Ziegler T., and Rauk A. Theor. Chim. Acta 46 (1977) 1
135. Ziegler T., and Rauk A. Inorg. Chem. 18 (1979) 1558
136. Ziegler T. NATO ASI C 378 (1992) 367
137. Bickelhaupt F.M., and Baerends E.J. Rev. Comp. Chem. 15 (2000) 1
138. Jacobsen H., and Ziegler T. Comment. Inorg. Chem. 17 (1995) 301
139. Jacobsen H., and Ziegler T. J. Am. Chem. Soc. 116 (1994) 3667
140. Martinho Simões J.A., and Beauchamp J.L. Chem. Rev. 90 (1990) 629
141. Rosa A., Ricciardi G., and Baerends E.J. J. Phys. Chem. A 110 (2006) 5180
142. Kitaura K., and Morokuma K. Int. J. Quantum Chem. 10 (1976) 325
143. Fujimoto H., Osamura Y., and Minato J. J. Am. Chem. Soc. 100 (1978) 2954
144. van den Hoek P.J., Kleyn A.W., and Baerends E.J. Comments At. Mol. Phys. 23 (1989) 93
145. Ziegler T., Tschinke V., and Becke A. J. Am. Chem. Soc. 109 (1987) 1351
146. Ziegler T., Tschinke V., and Ursenbach C. J. Am. Chem. Soc. 109 (1987) 4825
147. Bagus P.S., Herrmann K., and Bauschlicher Jr. C.W. J. Chem. Phys. 80 (1984) 4378
148. Bagus P.S., and Illas F. J. Chem. Phys. 96 (1992) 8962
149. Kraatz H.-B., Jacobsen H., Ziegler T., and Boorman P.M. Organometallics 12 (1993) 76
150. Jacobsen H., and Fink M.J. Inorg. Chim. Acta 360 (2007) 3511
151. Jacobsen H., Berke H., Doring S., Kehr G., Erker G., Fröhlich R., and Meyer O. Organometallics 18 (1999) 1724
152. Herrmann W.A., Schutz J., Frey G.D., and Herdtweck E. Organometallics 25 (2006) 2437
153. Mankad N.P., Gray T.G., Laitar D.S., and Sadighi J.P. Organometallics 23 (2004) 1191
154. Ramnial T., Abernethy C.D., Spicer M.D., McKenzie I.D., Gay I.D., and Clyburne J.A.C. Inorg. Chem. 42 (2003) 1391
155. Bohler C., Stein D., Donati N., and Grutzmacher H. New J. Chem. 26 (2002) 1291
156. Laitar D.S., Muller P., Gray T.G., and Sadighi J.P. Organometallics 24 (2005) 4503
157. Baker M.V., Barnard P.J., Brayshaw S.K., Hickey J.L., Skelton B.W., and White A.H. Dalton Trans. (2005) 37
158. Caddick S., Cloke F.G.N., Hitchcock P.B., and Lewis A.K.D. Angew. Chem. Int. Ed. 43 (2004) 5824
159. Jackstell R., Andreu M.G., Frisch A., Selvakumar K., Zapf A., Klein H., Spannenberg A., Rottger D., Briel O., Karch R., and Beller M. Angew. Chem. Int. Ed. 41 (2002) 986
160. Dorta R., Stevens E.D., Hoff C.D., and Nolan S.P. J. Am. Chem. Soc. 125 (2003) 10490
161. Markò I.E., Sterin S., Buisine O., Mignani R., Branlard P., Tinant B., and Declercq J.P. Science 298 (2002) 204
162. Huttner G., and Gartzke W. Chem. Ber. 105 (1972) 2714
163. Abdur-Rashid K., Fedorkiw T., Lough A.J., and Morris R.H. Organometallics 23 (2004) 86
164. Herrmann W.A., Elison M., Fischer J., Kocher C., and Artus G.R.J. Chem. Eur. J. 2 (1996) 772
165. Yamaguchi Y., Oda R., Sado K., Kobayashi K., Minato M., and Ito T. Bull. Chem. Soc. Jpn. 76 (2003) 991
166. Herrmann W.A., Goossen L.J., Artus G.R.J., and Kocher C. Organometallics 16 (1997) 2472
167. Niehues M., Kehr G., Fröhlich R., and Erker G. Zeitschrift fur Naturforschung B 58 (2003) 1005
168. Goldman A.S., and Krogh-Jespersen K. J. Am. Chem. Soc. 118 (1996) 12159