SCOPUS 정보 검색 플랫폼

Volumn 70, Issue 6, 2005, Pages 2391-2393

Silver(I)-carbene complexes/ionic liquids: Novel N-heterocyclic carbene delivery agents for organocatalytic transformations

(4) Sentman, Alan C c Csihony, Szilárd c Waymouth, Robert M b Hedrick, James L a

a IBM ALMADEN RESEARCH CENTER (United States)

b STANFORD UNIVERSITY (United States)

c NONE

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; ESTERIFICATION; MOLECULAR WEIGHT; PYROLYSIS; REACTION KINETICS; RING OPENING POLYMERIZATION;

CARBENES; IONIC LIQUIDS; N-HETEROCYCLIC CARBENE (NHC); TRANSESTERIFICATION;

SILVER COMPOUNDS;

CARBENOID; HETEROCYCLIC COMPOUND; IMIDAZOLIDINE DERIVATIVE; POLYLACTIDE; SILVER DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; DECOMPOSITION; LIQUID; MOLECULAR WEIGHT; POLYMERIZATION; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; TEMPERATURE; TRANSESTERIFICATION;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SILVER; TEMPERATURE;

EID: 15444376280 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo048555q Document Type: Article

Times cited : (104)

References (38)

1
- 0000658780
- (a) Wanzlick, H. W.; Kleiner, H. J. Angew. Chem. 1961, 73, 493.
- (1961) Angew. Chem. , vol.73 , pp. 493
- Wanzlick, H.W.¹ Kleiner, H.J.²

2
- 0000504565
- (b) Wanzlick, H. W. Angew. Chem. 1082, 74, 129.
- (1082) Angew. Chem. , vol.74 , pp. 129
- Wanzlick, H.W.¹

3
- 84981751972
- (c) Wanzlick, H. W.; Esser, T.; Kleiner, H. J. Chem. Ber. 1863, 96, 1208.
- (1863) Chem. Ber. , vol.96 , pp. 1208
- Wanzlick, H.W.¹ Esser, T.² Kleiner, H.J.³

4
- 0001286592
- (a) Arduengo, A. J.; Dais, R. L.; Harlow, R.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 361-363
- Arduengo, A.J.¹ Dais, R.L.² Harlow, R.³ Kline, M.⁴

5
- 0000793212
- (b) Arduengo, A. J.; Dais, R. L.; Harlow, R.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 5530-5534
- Arduengo, A.J.¹ Dais, R.L.² Harlow, R.³ Kline, M.⁴

6
- 0032723198
- (c) Arduengo, A. J. Acc. Chem. Res. 1999, 32, 913-921.
- (1999) Acc. Chem. Res. , vol.32 , pp. 913-921
- Arduengo, A.J.¹

7
- 0002556212
- (d) Arduengo, A. J.; Krfczyk, R. Chem. Z. 1998, 32, 6.
- (1998) Chem. Z. , vol.32 , pp. 6
- Arduengo, A.J.¹ Krfczyk, R.²

8
- 0000122520
- For example: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750. (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162-2168. (d) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648. (e) Haung, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- (2002) Angew. Chem. , vol.114 , pp. 1342-1363
- Herrmann, W.A.¹

9
- 0037090932
- For example: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750. (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162-2168. (d) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648. (e) Haung, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1290-1309
- Herrmann, W.A.¹

10
- 0035977649
- For example: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750. (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162-2168. (d) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648. (e) Haung, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 749-750
- Sanford, M.S.¹ Ulman, M.² Grubbs, R.H.³

11
- 0000443072
- For example: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750. (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162-2168. (d) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648. (e) Haung, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- (1998) Organometallics , vol.17 , pp. 2162-2168
- Herrmann, W.A.¹ Goossen, L.J.² Spiegler, M.³

12
- 0035930791
- For example: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750. (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162-2168. (d) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648. (e) Haung, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- (2001) Chem. Commun. , pp. 2648
- Choi, T.-L.¹ Grubbs, R.H.²

13
- 0000122520
- For example: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342-1363. (b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309. (b) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750. (c) Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162-2168. (d) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648. (e) Haung, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- (1999) Organometallics , vol.18 , pp. 2370-2375
- Haung, J.¹ Schanz, H.-J.² Stevens, E.D.³ Nolan, S.P.⁴

14
- 3142640259
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (1958) J. Am. Chem. Soc. , vol.80 , pp. 3719-3726
- Breslow, R.¹

15
- 0001300938
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (1976) Angew. Chem. , vol.88 , pp. 695
- Stetter, H.¹

16
- 84982417601
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 639-647
- Stetter, H.¹

17
- 0000430035
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (1996) Helv. Chim. Acta , vol.79 , pp. 1217-1221
- Enders, D.¹ Breuer, J.H.² Teles, J.H.³

18
- 0002505045
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (1996) Helv. Chim. Acta , vol.79 , pp. 61-83
- Teles, J.¹ Melder, J.² Ebel, K.³ Enders, D.⁴ Breuer, J.H.⁵

19
- 0037019628
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 10298-10299
- Kerr, M.S.¹ Read De Alaniz, J.² Rovis, T.³

20
- 0012570714
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (2002) Angew. Chem. , vol.114 , pp. 1822-1844
- Enders, D.¹ Kallfass, U.²

21
- 0036263823
- For example: (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726. (b) Stetter, H. Angew. Chem. 1976, 88, 695. (c) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647. (d) Enders, D.; Breuer, J. H.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217-1221. (e) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61-83. (f) Kerr, M. S.; Read De Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. (g) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822-1844. (h) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745;
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1743-1745
- Enders, D.¹ Kallfass, U.²

22
- 0037065680
- (a) Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 12, 914-915.
- (2002) J. Am. Chem. Soc. , vol.12 , pp. 914-915
- Connor, E.F.¹ Nyce, G.W.² Myers, M.³ Möck, A.⁴ Hedrick, J.L.⁵

23
- 0000926963
- (b) Grasa, G. A.; Kissling R. M.; Nolan S. P. Org. Lett. 2002, 4, 3583-3586.
- (2002) Org. Lett. , vol.4 , pp. 3583-3586
- Grasa, G.A.¹ Kissling, R.M.² Nolan, S.P.³

24
- 0037433492
- Nyce, G. W.; Glauser, T.; Connor, E. F.; Möck, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046-3056.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3046-3056
- Nyce, G.W.¹ Glauser, T.² Connor, E.F.³ Möck, A.⁴ Waymouth, R.M.⁵ Hedrick, J.L.⁶

25
- 33748638041
- (a) Cetinkaya, B.; Cetinkaya, E.; Chamizo, J. A.; Hitchcock, P. B.; Jasim, H. A.; Kücükbay, H.; Lappert, M. F. J. Chem. Soc., Perkin Trans. 1 1998, 2047-2054.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2047-2054
- Cetinkaya, B.¹ Cetinkaya, E.² Chamizo, J.A.³ Hitchcock, P.B.⁴ Jasim, H.A.⁵ Kücükbay, H.⁶ Lappert, M.F.⁷

26
- 84981751972
- (b) Wanzlick, H. W.; Esser, F.; Kleiner, H. J. Chem. Ber. 1963, 1208-1212.
- (1963) J. Chem. Ber. , pp. 1208-1212
- Wanzlick, H.W.¹ Esser, F.² Kleiner, H.³

27
- 0037420362
- (c) Trnka, T. A.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 12, 2546.
- (2003) J. Am. Chem. Soc. , vol.12 , pp. 2546
- Trnka, T.A.¹ Morgan, J.P.² Sanford, M.S.³ Wilhelm, T.E.⁴ Scholl, M.⁵ Choi, T.-L.⁶ Ding, S.⁷ Day, M.W.⁸ Grubbs, R.H.⁹

28
- 0033598258
- (d) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
- (1999) Org. Lett. , vol.1 , pp. 953
- Scholl, M.¹ Ding, S.² Lee, C.W.³ Grubbs, R.H.⁴

29
- 4444278874
- (e) Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem. Eur. J. 2004, 10, 4073-4079.
- (2004) Chem. Eur. J. , vol.10 , pp. 4073-4079
- Nyce, G.W.¹ Csihony, S.² Waymouth, R.M.³ Hedrick, J.L.⁴

30
- 0001618250
- (a) Arduengo, A. J.; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. Organometallics 1993, 12, 3405.
- (1993) Organometallics , vol.12 , pp. 3405
- Arduengo, A.J.¹ Dias, H.V.R.² Calabrese, J.C.³ Davidson, F.⁴

31
- 0000004671
- (b) Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972.
- (1998) Organometallics , vol.17 , pp. 972
- Wang, H.M.J.¹ Lin, I.J.B.²

32
- 0002978116
- (c) Tulloch, A. A. D.; Danopoulos, A. D.; Winston, S.; Kleinhenz, S.; Eastham, G. Dalton Trans. 2000, 24, 4499-4056.
- (2000) Dalton Trans. , vol.24 , pp. 4499-14056
- Tulloch, A.A.D.¹ Danopoulos, A.D.² Winston, S.³ Kleinhenz, S.⁴ Eastham, G.⁵

33
- 0035968385
- Pytkowicz, J.; Roland, S.; Mangeney, P. Tetrahedron: Asymmetry 2001, 12, 2087-2089
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 2087-2089
- Pytkowicz, J.¹ Roland, S.² Mangeney, P.³

34
- 84866203947
- Kuhn, N.; Bohnen, H.; Henkel, G. Z. Naturforsch. 1994, 49b, 1473-1480.
- (1994) Z. Naturforsch. , vol.49 B , pp. 1473-1480
- Kuhn, N.¹ Bohnen, H.² Henkel, G.³

35
- 84982456836
- Schlösser, W.; Regitz, M. Chem. Ber. 1974, 107, 1931.
- (1974) Chem. Ber. , vol.107 , pp. 1931
- Schlösser, W.¹ Regitz, M.²

36
- 0000913836
- (a) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587-3590.
- (2002) Org. Lett. , vol.4 , pp. 3587-3590
- Nyce, G.W.¹ Lamboy, J.A.² Connor, E.F.³ Waymouth, R.M.⁴ Hedrick, J.L.⁵

37
- 0242500893
- (b) Grasa G. A.; Guveli T.; Singh R.; Nolan S. P. J. Org. Chem. 2003, 68, 2812-2819.
- (2003) J. Org. Chem. , vol.68 , pp. 2812-2819
- Grasa, G.A.¹ Guveli, T.² Singh, R.³ Nolan, S.P.⁴

38
- 15444364816
- note
- Elemental analysis has proven difficult to obtain for the silver complexes. Evidence of compound purity is given by NMR and MS data in the Supporting Information.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.