메뉴 건너뛰기




Volumn 11, Issue 6, 2005, Pages 1833-1853

Diaminocarbene- and Fischer-carbene complexes of palladium and nickel by oxidative insertion: Preparation, structure, and catalytic activity

Author keywords

Carbenes; Cross coupling; Homogeneous catalysis; Nickel; Palladium

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; COMPLEXATION; NICKEL COMPOUNDS; OXIDATION; PALLADIUM COMPOUNDS; REACTION KINETICS; SALTS; X RAY CRYSTALLOGRAPHY;

EID: 15044351678     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400928     Document Type: Article
Times cited : (211)

References (187)
  • 1
    • 0000504565 scopus 로고
    • a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80;
    • (1962) Angew. Chem. , vol.74 , pp. 129-134
    • Wanzlick, H.-W.1
  • 2
    • 33745926045 scopus 로고
    • a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80;
    • (1962) Angew. Chem. Int. Ed. Engl. , vol.1 , pp. 75-80
  • 4
    • 84981776828 scopus 로고
    • b) H.-W. Wanzlick, H. J. Schönherr, Angew. Chem. 1968, 80, 154; Angew. Chem. Int. Ed. Engl. 1968, 7, 141-142.
    • (1968) Angew. Chem. Int. Ed. Engl. , vol.7 , pp. 141-142
  • 13
    • 33845279754 scopus 로고
    • Arduengo's isolation of a stable NHC was predated by the isolation of a stable phosphinocarbene species by Bertrand et al. Although this latter species has been somewhat controversial as it might also be formulated as a phosphaacetylene, this discovery marks the actual start of the "stable carbene" era, cf. A. Igau, H. Grützmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1988, 110, 6463-6466.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6463-6466
    • Igau, A.1    Grützmacher, H.2    Baceiredo, A.3    Bertrand, G.4
  • 14
    • 0011217613 scopus 로고    scopus 로고
    • Reviews: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1343-1363; Angew. Chem. Int. Ed. 2002, 41, 1290-1309;
    • (2002) Angew. Chem. , vol.114 , pp. 1343-1363
    • Herrmann, W.A.1
  • 15
    • 0037090932 scopus 로고    scopus 로고
    • Reviews: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1343-1363; Angew. Chem. Int. Ed. 2002, 41, 1290-1309;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1290-1309
  • 16
    • 0000419378 scopus 로고    scopus 로고
    • b) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
    • (1997) Angew. Chem. , vol.109 , pp. 2256-2282
    • Herrmann, W.A.1    Köcher, C.2
  • 17
    • 0030660076 scopus 로고    scopus 로고
    • b) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2162-2187
  • 18
    • 0347870368 scopus 로고    scopus 로고
    • For reviews on other application of N-heterocyclic carbenes as reagents and catalysts in organic synthesis see: a) D. Enders, H. Gielen, J. Organomet. Chem. 2001, 617-618, 70-80;
    • (2001) J. Organomet. Chem. , vol.617-618 , pp. 70-80
    • Enders, D.1    Gielen, H.2
  • 21
    • 0000785058 scopus 로고    scopus 로고
    • b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
    • (2000) Angew. Chem. , vol.112 , pp. 3140-3172
    • Fürstner, A.1
  • 22
    • 0001399412 scopus 로고    scopus 로고
    • b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012-3043
  • 23
    • 0004515138 scopus 로고    scopus 로고
    • See the following for leading references on the use of metal-NHC complexes as catalysts for Suzuki reactions: a) T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 1999, 585, 348-352;
    • (1999) J. Organomet. Chem. , vol.585 , pp. 348-352
    • Weskamp, T.1    Böhm, V.P.W.2    Herrmann, W.A.3
  • 26
    • 0037090921 scopus 로고    scopus 로고
    • c) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421-1423; Angew. Chem. Int. Ed. 2002, 41, 1363-1365;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1363-1365
  • 28
    • 0042969355 scopus 로고    scopus 로고
    • d) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818-3821; Angew. Chem. Int. Ed. 2003, 42, 3690-3693;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3690-3693
  • 39
    • 4143134810 scopus 로고    scopus 로고
    • b) L. H. Gade, V. César, S. Bellemin-Laponnaz, Angew. Chem. 2004, 116, 1036-1039; Angew. Chem. Int. Ed. 2004, 43, 1014-1017;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1014-1017
  • 43
    • 33750386593 scopus 로고
    • For the generation of NHC's by α-elimination see the following references and literature therein: a) D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Chem. 1995, 107, 1119-1122; Angew. Chem. Int. Ed. Engl. 1995, 34, 1021-1023;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1021-1023
  • 45
    • 0027288006 scopus 로고
    • For the generation of NHC by reductive desulfurization see the following references and literature therein: a) N. Kuhn, T. Kratz, Synthesis 1993, 561-562;
    • (1993) Synthesis , pp. 561-562
    • Kuhn, N.1    Kratz, T.2
  • 47
    • 15044359716 scopus 로고    scopus 로고
    • note
    • For the use of electron rich olefins as carbene sources see ref. [3].
  • 51
    • 15044356096 scopus 로고    scopus 로고
    • c) W. Kirmse, Angew. Chem. 2004, 116, 1799-1801; Angew. Chem. Int. Ed. 2004, 43, 1767-1769.
    • (2004) Angew. Chem. , vol.116 , pp. 1799-1801
    • Kirmse, W.1
  • 52
    • 3242700914 scopus 로고    scopus 로고
    • c) W. Kirmse, Angew. Chem. 2004, 116, 1799-1801; Angew. Chem. Int. Ed. 2004, 43, 1767-1769.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1767-1769
  • 58
    • 0001602606 scopus 로고    scopus 로고
    • a) The pronounced σ-donation capacity of NHC's in combination with their poor π-acceptor properties is considered to be one of the major advantages of this class of ancillary ligands. Therefore it is of particular interest to note that the acyclic diaminocarbene F is an even stronger σ-donor than its cyclic counterparts, cf. R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211-1213; Angew. Chem. Int. Ed. Engl. 1996, 35, 1121-1123;
    • (1996) Angew. Chem. , vol.108 , pp. 1211-1213
    • Alder, R.W.1    Allen, P.R.2    Murray, M.3    Orpen, A.G.4
  • 59
    • 33748242162 scopus 로고    scopus 로고
    • a) The pronounced σ-donation capacity of NHC's in combination with their poor π-acceptor properties is considered to be one of the major advantages of this class of ancillary ligands. Therefore it is of particular interest to note that the acyclic diaminocarbene F is an even stronger σ-donor than its cyclic counterparts, cf. R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211-1213; Angew. Chem. Int. Ed. Engl. 1996, 35, 1121-1123;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1121-1123
  • 68
    • 84943057575 scopus 로고
    • For other methods allowing for the formation of metal complexes bearing non-cyclic (di)aminocarbene ligands see for example: a) K. Öfele, C. G. Kreiter, Chem. Ber. 1972, 105, 529-540;
    • (1972) Chem. Ber. , vol.105 , pp. 529-540
    • Öfele, K.1    Kreiter, C.G.2
  • 84
    • 0035925184 scopus 로고    scopus 로고
    • For recent examples for the formation of metal-carbene complexes by oxidative insertion into the C-H bond of imidazolium salts see: a) D. S. McGuinness, K. J. Cavell, B. F. Yates, Chem. Commun. 2001, 355-356;
    • (2001) Chem. Commun. , pp. 355-356
    • McGuinness, D.S.1    Cavell, K.J.2    Yates, B.F.3
  • 88
    • 2942545879 scopus 로고    scopus 로고
    • d) N. D. Clement, K. J. Cavell, C. Jones, C. J. Elsevier, Angew. Chem. 2004, 116, 1297-1299; Angew. Chem. Int. Ed. 2004, 43, 1277-1279;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1277-1279
  • 98
    • 0142048782 scopus 로고
    • a) W. Petz, Angew. Chem. 1975, 87, 288; Angew. Chem. Int. Ed. Engl. 1975, 14, 367;
    • (1975) Angew. Chem. , vol.87 , pp. 288
    • Petz, W.1
  • 99
    • 84982355728 scopus 로고
    • a) W. Petz, Angew. Chem. 1975, 87, 288; Angew. Chem. Int. Ed. Engl. 1975, 14, 367;
    • (1975) Angew. Chem. Int. Ed. Engl. , vol.14 , pp. 367
  • 109
    • 0000655751 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • a) W. Kantlehner, in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 485-599;
    • (1991) Comprehensive Organic Synthesis, Vol. 6 , vol.6 , pp. 485-599
    • Kantlehner, W.1
  • 110
    • 0003418644 scopus 로고
    • Iminium salts in organic chemistry, Part 2
    • Wiley, New York
    • b) Iminium Salts in Organic Chemistry, Part 2 (Eds.: H. Böhme, H. G. Viehe), Adv. Org. Chem., Vol. 9, Wiley, New York, 1979.
    • (1979) Adv. Org. Chem., Vol. 9 , vol.9
    • Böhme, H.1    Viehe, H.G.2
  • 121
    • 15044345405 scopus 로고    scopus 로고
    • note
    • For the structure and further details see ref. [24].
  • 122
    • 37049141200 scopus 로고
    • 3)(NHC)] prepared during this study are cis configured likely reflects their higher thermodynamic stability as compared to the trans-counterparts, cf. B. Cetinkaya, E. Cetinkaya, M. F. Lappert, J. Chem. Soc. Dalton Trans. 1973, 906-912.
    • (1973) J. Chem. Soc. Dalton Trans. , pp. 906-912
    • Cetinkaya, B.1    Cetinkaya, E.2    Lappert, M.F.3
  • 126
    • 0037453328 scopus 로고    scopus 로고
    • For recent reviews on the preparation and use of enantiopure NHC's and metal-NHC complexes see ref. [7] and the following: M. C. Perry, K. Burgess, Tetrahedron: Asymmetry 2003, 14, 951-961.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 951-961
    • Perry, M.C.1    Burgess, K.2
  • 127
    • 15044346362 scopus 로고    scopus 로고
    • note
    • For related complexes prepared by conventional ligand exchange methodology see ref. [19c].
  • 130
    • 15044350590 scopus 로고    scopus 로고
    • See ref. [18b]
    • a) See ref. [18b];
  • 132
    • 15044344213 scopus 로고    scopus 로고
    • note
    • c) very recently, the half life of this species in THF solution was determined to be "a few hours at 0°C", cf. ref. [17b].
  • 139
    • 0037176243 scopus 로고    scopus 로고
    • Correction
    • f) J. Louie, J. E. Gibby, M. V. Farnworth, T. N. Tekavec, J. Am. Chem. Soc. 2002, 124, 15188-15189; correction: J. Am. Chem. Soc. 2004, 126, 8590;
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8590
  • 140
    • 15044361327 scopus 로고    scopus 로고
    • g) G. Zuo, J. Louie, Angew. Chem. 2004, 116, 2327-2329; Angew. Chem. Int. Ed. 2004, 43, 2277-2279;
    • (2004) Angew. Chem. , vol.116 , pp. 2327-2329
    • Zuo, G.1    Louie, J.2
  • 141
    • 4544385916 scopus 로고    scopus 로고
    • g) G. Zuo, J. Louie, Angew. Chem. 2004, 116, 2327-2329; Angew. Chem. Int. Ed. 2004, 43, 2277-2279;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2277-2279
  • 148
    • 4344692348 scopus 로고    scopus 로고
    • Cross-coupling reactions. A practical guide
    • Springer, Berlin
    • b) Cross-Coupling Reactions. A Practical Guide (Ed.: N. Miyaura), Top. Curr. Chem., Vol. 219, Springer, Berlin, 2002;
    • (2002) Top. Curr. Chem., Vol. 219 , vol.219
    • Miyaura, N.1
  • 152
    • 0000279636 scopus 로고
    • b) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
    • (1994) Angew. Chem. , vol.106 , pp. 2473-2506
    • De Meijere, A.1    Meyer, F.E.2
  • 153
    • 0001217660 scopus 로고
    • b) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2379-2411
  • 154
    • 0000602884 scopus 로고
    • See the following for leading references on the use of metal-NHC complexes as catalysts for Heck reactions: a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605; Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374;
    • (1995) Angew. Chem. , vol.107 , pp. 2602-2605
    • Herrmann, W.A.1    Elison, M.2    Fischer, J.3    Köcher, C.4    Artus, G.R.J.5
  • 155
    • 33749349096 scopus 로고
    • See the following for leading references on the use of metal-NHC complexes as catalysts for Heck reactions: a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605; Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2371-2374
  • 166
    • 0000897978 scopus 로고    scopus 로고
    • b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
    • (1998) Angew. Chem. , vol.110 , pp. 2154-2177
    • Hartwig, J.F.1
  • 167
    • 0032541260 scopus 로고    scopus 로고
    • b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2046-2067
  • 170
    • 0001152076 scopus 로고    scopus 로고
    • See the following for leading references on the use of metal-NHC complexes as catalysts for amination reactions: a) J. Huang, G. Grasa, S. P. Nolan, Org. Lett. 1999, 1, 1307-1309;
    • (1999) Org. Lett. , vol.1 , pp. 1307-1309
    • Huang, J.1    Grasa, G.2    Nolan, S.P.3
  • 174
    • 8444233339 scopus 로고    scopus 로고
    • It is likely that monoligated Pd species constitute the actual active catalysts in situ; monoligation is favored by increased steric bulk of the ligand. For a more detailed discussion see the following review and the literature therein: M. Miura, Angew. Chem. 2004, 116, 2251-2253; Angew. Chem. Int. Ed. 2004, 43, 2201-2203.
    • (2004) Angew. Chem. , vol.116 , pp. 2251-2253
    • Miura, M.1
  • 175
    • 3242659154 scopus 로고    scopus 로고
    • It is likely that monoligated Pd species constitute the actual active catalysts in situ; monoligation is favored by increased steric bulk of the ligand. For a more detailed discussion see the following review and the literature therein: M. Miura, Angew. Chem. 2004, 116, 2251-2253; Angew. Chem. Int. Ed. 2004, 43, 2201-2203.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2201-2203
  • 177
    • 0033610452 scopus 로고    scopus 로고
    • For Kumada cross-coupling reactions using metal-NHC catalysts see: a) J. Huang, S. P. Nolan, J. Am. Chem. Soc. 1999, 121, 9889-9890;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9889-9890
    • Huang, J.1    Nolan, S.P.2
  • 179
    • 0037484660 scopus 로고    scopus 로고
    • b) V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. 2000, 112, 1672-1674; Angew. Chem. Int. Ed. 2000, 39, 1602-1604;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1602-1604


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.