SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 128, Issue 44, 2006, Pages 14306-14317

DFT study on the palladium-catalyzed allylation of primary amines by allylic alcohol

(4) Piechaczyk, Olivier a Thoumazet, Claire a Jean, Yves a Floch, Pascal Le a

a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; COMPLEXATION; MATHEMATICAL MODELS; PALLADIUM; POSITIVE IONS; PROBABILITY DENSITY FUNCTION;

ALLYLATION; ALLYLIC ALCOHOL; DECOMPLEXATION; HYDRIDOPALLADIUM COMPLEX;

AMINES;

ALCOHOL; AMINE; AMMONIUM DERIVATIVE; CARBON; CATION; LIGAND; METAL; PALLADIUM; PALLADIUM COMPLEX; PROTON;

ALLYLATION; ARTICLE; CALCULATION; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; DECOMPOSITION; DENSITY FUNCTIONAL THEORY; ELECTRON; PRECURSOR; PROTON TRANSPORT; REACTION ANALYSIS;

ALGORITHMS; ALLYL COMPOUNDS; AMINES; CARBON; CATALYSIS; LIGANDS; MODELS, THEORETICAL; NITROGEN; PALLADIUM; PROPANOLS; PROTONS; QUATERNARY AMMONIUM COMPOUNDS; THERMODYNAMICS;

EID: 33750702852 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja0621997 Document Type: Article

Times cited : (86)

References (63)

1
- 0009726999
- Atta-Ur-Rahman, Ed.; Harwood Academic Publishers: Harwood
- (a) Trost, B. M. In Advances in Natural Product Chemistry; Atta-Ur-Rahman, Ed.; Harwood Academic Publishers: Harwood, 1992; pp 19-34.
- (1992) Advances in Natural Product Chemistry , pp. 19-34
- Trost, B.M.¹

2
- 0042379988
- (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
- (2003) Chem. Rev. , vol.103 , pp. 2921-2943
- Trost, B.M.¹ Crawley, M.L.²

3
- 16244407390
- (a) Muzart, J. Tetrahedron 2005, 61, 4179-4212.
- (2005) Tetrahedron , vol.61 , pp. 4179-4212
- Muzart, J.¹

4
- 0032556663
- (b) Bricout, H.; Carpentier, J.-F.; Mortreux, A. J. Mol. Catal. A 1998, 136, 243-251.
- (1998) J. Mol. Catal. A , vol.136 , pp. 243-251
- Bricout, H.¹ Carpentier, J.-F.² Mortreux, A.³

5
- 0037176296
- (c) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 15164-15165
- Ohmura, T.¹ Hartwig, J.F.²

6
- 0000276556
- Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
- (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 585-661.
- (1991) Comprehensive Organic Synthesis , vol.4 , pp. 585-661
- Godleski, S.A.¹

7
- 0000711315
- Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
- (e) Davis, J. A. In Comprehensive Organometallic Chemistry 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 9, p 291.
- (1995) Comprehensive Organometallic Chemistry 11 , vol.9 , pp. 291
- Davis, J.A.¹

8
- 0035385137
- (f) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
- (2001) Chem. Rev. , vol.101 , pp. 2067-2096
- Trost, B.M.¹ Toste, F.D.² Pinkerton, A.B.³

9
- 6844254916
- (g) Trost, B. M.; VanVranken, D. L. Chem. Rev. 1996, 96, 395-422.
- (1996) Chem. Rev. , vol.96 , pp. 395-422
- Trost, B.M.¹ Vanvranken, D.L.²

10
- 0001312564
- (h) Trost, B. M. Acc. Chem. Res. 1980, 13, 385-393.
- (1980) Acc. Chem. Res. , vol.13 , pp. 385-393
- Trost, B.M.¹

11
- 9144258517
- (i) Garcia-Yebra, C.; Janssen, J. P.; Rominger, F.; Helmchen, G. Organometallics 2004, 23, 5459-5470.
- (2004) Organometallics , vol.23 , pp. 5459-5470
- Garcia-Yebra, C.¹ Janssen, J.P.² Rominger, F.³ Helmchen, G.⁴

12
- 0000199659
- (j) Glorius, F.; Pfaltz, A. Org. Lett. 1999, 1, 141-144.
- (1999) Org. Lett. , vol.1 , pp. 141-144
- Glorius, F.¹ Pfaltz, A.²

13
- 0033949478
- (k) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
- (2000) Acc. Chem. Res. , vol.33 , pp. 336-345
- Helmchen, G.¹ Pfaltz, A.²

14
- 0033592797
- (l) Fuji, K.; Kinoshita, N.; Tanaka, K.; Kawabata, T. Chem. Commun. 1999, 2289-2290.
- (1999) Chem. Commun. , pp. 2289-2290
- Fuji, K.¹ Kinoshita, N.² Tanaka, K.³ Kawabata, T.⁴

15
- 33845378604
- (m) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046.
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 2033-2046
- Auburn, P.R.¹ Mackenzie, P.B.² Bosnich, B.³

16
- 14644412315
- (a) Tang, D. Y.; Luo, X. L.; Shen, W.; Li, M. J. Mol. Struct. (THEOCHEM) 2005, 716, 79-87.
- (2005) J. Mol. Struct. (THEOCHEM) , vol.716 , pp. 79-87
- Tang, D.Y.¹ Luo, X.L.² Shen, W.³ Li, M.⁴

17
- 0034665223
- (b) Amatore, C.; Gamez, S.; Jutand, A.; Meyer, G.; Moreno-Manas, M.; Mortal, L.; Pleixats, R. Chem.-Eur. J. 2000, 6, 3372-3376.
- (2000) Chem.-Eur. J. , vol.6 , pp. 3372-3376
- Amatore, C.¹ Gamez, S.² Jutand, A.³ Meyer, G.⁴ Moreno-Manas, M.⁵ Mortal, L.⁶ Pleixats, R.⁷

18
- 0037101666
- (c) Kollmar, M.; Steinhagen, H.; Janssen, J. P.; Goldfuss, B.; Malinovskaya, S. A.; Vazquez, J.; Rominger, F.; Helmchen, G. Chem.-Eur. J. 2002, 8, 3103-3114.
- (2002) Chem.-Eur. J. , vol.8 , pp. 3103-3114
- Kollmar, M.¹ Steinhagen, H.² Janssen, J.P.³ Goldfuss, B.⁴ Malinovskaya, S.A.⁵ Vazquez, J.⁶ Rominger, F.⁷ Helmchen, G.⁸

19
- 0035914628
- (d) Kollmar, M.; Goldfuss, B.; Reggelin, M.; Rominger, F.; Helmchen, G. Chem.-Eur. J. 2001, 7, 4913-4927.
- (2001) Chem.-Eur. J. , vol.7 , pp. 4913-4927
- Kollmar, M.¹ Goldfuss, B.² Reggelin, M.³ Rominger, F.⁴ Helmchen, G.⁵

20
- 0001758225
- (e) Dedieu, A. Chem. Rev. 2000, 100, 543-600.
- (2000) Chem. Rev. , vol.100 , pp. 543-600
- Dedieu, A.¹

21
- 0000446913
- (f) Blochl, P. E.; Togni, A. Organometallics 1996, 15, 4125-4132.
- (1996) Organometallics , vol.15 , pp. 4125-4132
- Blochl, P.E.¹ Togni, A.²

22
- 33644798263
- (g) Amatore, C.; Jutand, A.; Mensah, L.; Meyer, G.; Fiaud, J. C.; Legros, J. Y. Em. J. Org. Chem. 2006, 1185-1192.
- (2006) Em. J. Org. Chem. , pp. 1185-1192
- Amatore, C.¹ Jutand, A.² Mensah, L.³ Meyer, G.⁴ Fiaud, J.C.⁵ Legros, J.Y.⁶

23
- 0038271730
- (h) Jutand, A. Eur. J. Inorg. Chem. 2003, 2017-2040.
- (2003) Eur. J. Inorg. Chem. , pp. 2017-2040
- Jutand, A.¹

24
- 22144461766
- (a) Tamara, Y. Eur. J. Org. Chem. 2005, 2647-2656.
- (2005) Eur. J. Org. Chem. , pp. 2647-2656
- Tamara, Y.¹

25
- 0001374863
- (b) Tamara, Y. J. Organomet. Chem. 1999, 576, 215-231.
- (1999) J. Organomet. Chem. , vol.576 , pp. 215-231
- Tamara, Y.¹

26
- 0001019702
- (c) Lu, X. Y.; Jiang, X. H.; Tao, X. C. J. Organomet. Chem. 1988, 344, 109-118.
- (1988) J. Organomet. Chem. , vol.344 , pp. 109-118
- Lu, X.Y.¹ Jiang, X.H.² Tao, X.C.³

27
- 0022755664
- (d) Lu, X. Y.; Lu, L.; Sun, J. H. J. Mol. Catal. 1987, 41, 245-251.
- (1987) J. Mol. Catal. , vol.41 , pp. 245-251
- Lu, X.Y.¹ Lu, L.² Sun, J.H.³

28
- 0037130740
- Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968-10969.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 10968-10969
- Ozawa, F.¹ Okamoto, H.² Kawagishi, S.³ Yamamoto, S.⁴ Minami, T.⁵ Yoshifuji, M.⁶

29
- 4444360424
- Ozawa, F.; Yoshifuji, M. C. R. Chim. 2004, 7, 747-754.
- (2004) C. R. Chim. , vol.7 , pp. 747-754
- Ozawa, F.¹ Yoshifuji, M.²

30
- 15944404618
- Piechaczyk, O.; Doux, M.; Ricard, L.; Le Floch, P. Organometallics 2005, 24, 1204-1213.
- (2005) Organometallics , vol.24 , pp. 1204-1213
- Piechaczyk, O.¹ Doux, M.² Ricard, L.³ Le Floch, P.⁴

31
- 2342439178
- Ozawa, F.; Ishiyama, T.; Yamamoto, S.; Kawagishi, S.; Murakami, H.; Yoshifuji, M. Organometattics 2004, 23, 1698-1707.
- (2004) Organometattics , vol.23 , pp. 1698-1707
- Ozawa, F.¹ Ishiyama, T.² Yamamoto, S.³ Kawagishi, S.⁴ Murakami, H.⁵ Yoshifuji, M.⁶

32
- 84962361532
- (a) Takano, Y.; Houk, K. N. J. Chem. Theory Comput. 2005, 1, 70-77.
- (2005) J. Chem. Theory Comput. , vol.1 , pp. 70-77
- Takano, Y.¹ Houk, K.N.²

33
- 1642535349
- (b) Fu, Y.; Liu, L.; Li, R. C.; Liu, R.; Guo, Q. X. J. Am. Chem. Soc. 2004, 126, 814-822.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 814-822
- Fu, Y.¹ Liu, L.² Li, R.C.³ Liu, R.⁴ Guo, Q.X.⁵

34
- 0037130677
- (c) Baik, M. H.; Schauer, C. K.; Ziegler, T. J. Am. Chem. Soc. 2002, 124, 11167-11181.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 11167-11181
- Baik, M.H.¹ Schauer, C.K.² Ziegler, T.³

35
- 0037104792
- (d) Pliego, J. R.; Riveros, J. M. J. Phys. Chem. A 2002, 106, 7434-7439.
- (2002) J. Phys. Chem. A , vol.106 , pp. 7434-7439
- Pliego, J.R.¹ Riveros, J.M.²

36
- 0037042277
- (e) Lopez, X.; Schaefer, M.; Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 2002, 124, 5010-5018.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 5010-5018
- Lopez, X.¹ Schaefer, M.² Dejaegere, A.³ Karplus, M.⁴

37
- 21244498543
- (a) Nowroozi-Isfahani, T.; Musaev, D. G.; McDonald, F. E.; Morokuma, K. Organometallics 2005, 24, 2921-2929.
- (2005) Organometallics , vol.24 , pp. 2921-2929
- Nowroozi-Isfahani, T.¹ Musaev, D.G.² McDonald, F.E.³ Morokuma, K.⁴

38
- 84961973408
- (b) Marino, T.; Russo, N.; Toscano, M. J. Am. Chem. Soc. 2005, 127, 4242-4253.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4242-4253
- Marino, T.¹ Russo, N.² Toscano, M.³

39
- 84961986772
- (c) Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100-3109.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 3100-3109
- Casey, C.P.¹ Johnson, J.B.² Singer, S.W.³ Cui, Q.⁴

40
- 84962467697
- (d) Schubert, G.; Papai, I. J. Am. Chem. Soc. 2003, 125, 14847-14858.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14847-14858
- Schubert, G.¹ Papai, I.²

41
- 84962374892
- (e) Kovacs, G.; Papai, I. Organometallics 2006, 25, 820-825.
- (2006) Organometallics , vol.25 , pp. 820-825
- Kovacs, G.¹ Papai, I.²

42
- 0039785339
- Senn, H. M.; Blochl, P. E.; Togni, A. J. Am. Chem. Soc. 2000, 122, 4098-4107.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4098-4107
- Senn, H.M.¹ Blochl, P.E.² Togni, A.³

43
- 8744239436
- The assistance of molecules of water has been proposed in the literature and is supported by DFT calculations, see: Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 4085-4088.
- (2004) Org. Lett. , vol.6 , pp. 4085-4088
- Kinoshita, H.¹ Shinokubo, H.² Oshima, K.³

44
- 33244484834
- Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828-1839.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1828-1839
- Johns, A.M.¹ Utsunomiya, M.² Incarvito, C.D.³ Hartwig, J.F.⁴

45
- 0000808988
- Simoes, J. A. M.; Beauchamp, J. L. Chem. Rev. 1990, 90, 629-688.
- (1990) Chem. Rev. , vol.90 , pp. 629-688
- Simoes, J.A.M.¹ Beauchamp, J.L.²

46
- 32644448992
- Le Floch, P. Coord. Chem. Rev. 2006, 250, 627-681.
- (2006) Coord. Chem. Rev. , vol.250 , pp. 627-681
- Le Floch, P.¹

47
- 37049155415
- Chatt, J.; Duncanson, L. A. J. Chem. Soc. 1953, 2939-2947.
- (1953) J. Chem. Soc. , pp. 2939-2947
- Chatt, J.¹ Duncanson, L.A.²

48
- 0041464227
- Frenking, G.; Frohlich, N. Chem. Rev. 2000, 100, 717-774.
- (2000) Chem. Rev. , vol.100 , pp. 717-774
- Frenking, G.¹ Frohlich, N.²

49
- 6144226868
- Dapprich, S.; Frenking, G. J. Phys. Chem. 1995, 99, 9352-9362.
- (1995) J. Phys. Chem. , vol.99 , pp. 9352-9362
- Dapprich, S.¹ Frenking, G.²

50
- 1842451400
- 4] has been used to convert aniline in harsher conditions, see: Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595-2597.
- (2004) J. Org. Chem. , vol.69 , pp. 2595-2597
- Kayaki, Y.¹ Koda, T.² Ikariya, T.³

51
- 3042742728
- 4 is present in the reaction medium as water scavenger (with lower reaction rates).
- (2004) J. Org. Chem. , vol.69 , pp. 4482-4486
- Murakami, H.¹ Minami, T.² Ozawa, F.³

52
- 0009485062
- Zettlitzer, M.; Tom Dieck, H.; Haupt, E. T. K.; Stamp, L. Chem. Ber. 1986, 119, 1868-1875.
- (1986) Chem. Ber. , vol.119 , pp. 1868-1875
- Zettlitzer, M.¹ Tom Dieck, H.² Haupt, E.T.K.³ Stamp, L.⁴

53
- 0035116074
- Amatore, C.; Jutand, A.; M'Barki, M. A.; Meyer, G.; Mottier, L. Eur. J. Inorg. Chem. 2001, 873-880.
- (2001) Eur. J. Inorg. Chem. , pp. 873-880
- Amatore, C.¹ Jutand, A.² M'Barki, M.A.³ Meyer, G.⁴ Mottier, L.⁵

54
- 0141704726
- Gaussian, Inc.: Pitsburgh, PA
- Frisch, M. J.; et al. Gaussian 03, revision B.04; Gaussian, Inc.: Pitsburgh, PA, 2003.
- (2003) Gaussian 03, Revision B.04
- Frisch, M.J.¹

55
- 0000189651
- Becke, A. D. J. J. Phys. Chem. 1993, 98, 5648-5662.
- (1993) J. Phys. Chem. , vol.98 , pp. 5648-5662
- Becke, A.D.J.¹

56
- 33645898818
- Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244-13249.
- (1992) Phys. Rev. B , vol.45 , pp. 13244-13249
- Perdew, J.P.¹ Wang, Y.²

57
- 27344448074
- Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
- (1985) J. Chem. Phys. , vol.82 , pp. 299-310
- Hay, P.J.¹ Wadt, W.R.²

58
- 43949164303
- Ehlers, A. W.; Bohme, M.; Dapprich, S.; Gobbi, A.; Hollwarth, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111-114.
- (1993) Chem. Phys. Lett. , vol.208 , pp. 111-114
- Ehlers, A.W.¹ Bohme, M.² Dapprich, S.³ Gobbi, A.⁴ Hollwarth, A.⁵ Jonas, V.⁶ Kohler, K.F.⁷ Stegmann, R.⁸ Veldkamp, A.⁹ Frenking, G.¹⁰

59
- 2442521209
- (a) Barone, V.; Improta, R.; Rega, N. Theor. Chem. Ace. 2004, 111, 237-245.
- (2004) Theor. Chem. Ace. , vol.111 , pp. 237-245
- Barone, V.¹ Improta, R.² Rega, N.³

60
- 84961986752
- (b) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54.
- (2002) J. Chem. Phys. , vol.117 , pp. 43-54
- Cossi, M.¹ Scalmani, G.² Rega, N.³ Barone, V.⁴

61
- 84962359221
- (c) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
- (1996) Chem. Phys. Lett. , vol.255 , pp. 327-335
- Cossi, M.¹ Barone, V.² Cammi, R.³ Tomasi, J.⁴

62
- 84946893847
- (d) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
- (1981) Chem. Phys. , vol.55 , pp. 117-129
- Miertus, S.¹ Scrocco, E.² Tomasi, J.³

63
- 0042041206
- Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024-10035.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 10024-10035
- Rappe, A.K.¹ Casewit, C.J.² Colwell, K.S.³ Goddard, W.A.⁴ Skiff, W.M.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.