SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 22, 2013, Pages 5807-5812

Weak arene C-h×××o hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones

(6) Huang, Zhiyan a Chen, Zuliang a Lim, Li Hui a Quang, Gia Chuong Phan a Hirao, Hajime a Zhou, Jianrong a

a Nanyang Technological University (Singapore)

Author keywords

cross coupling; hydrogen bonds; lactones; palladium

Indexed keywords

ABSOLUTE CONFIGURATION; CROSS-COUPLINGS; LACTONES; PALLADIUM CATALYST; PALLADIUM-CATALYZED ARYLATION; STEREOCENTERS; VINYLATION; WEAK FORCE;

CATALYSTS; CHEMICAL REACTIONS; ESTERS; PALLADIUM;

HYDROGEN BONDS;

LACTONE; PALLADIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND;

CATALYSIS; HYDROGEN BONDING; LACTONES; MOLECULAR STRUCTURE; PALLADIUM; VINYL COMPOUNDS;

EID: 84878102161 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201300481 Document Type: Article

Times cited : (71)

References (74)

1
- 77349104061
- F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082
- (2010) Chem. Rev. , vol.110 , pp. 1082
- Bellina, F.¹ Rossi, R.²

2
- 77953484672
- C. C. C. Johansson, T. J. Colacot, Angew. Chem. 2010, 122, 686
- (2010) Angew. Chem. , vol.122 , pp. 686
- Johansson, C.C.C.¹ Colacot, T.J.²

3
- 74849140182
- Angew. Chem. Int. Ed. 2010, 49, 676
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 676

4
- 62349105130
- A. C. B. Burtoloso, Synlett 2009, 320
- (2009) Synlett , pp. 320
- Burtoloso, A.C.B.¹

5
- 84655162040
- J. Zhou, Synlett 2012, 1
- (2012) Synlett , pp. 1
- Zhou, J.¹

6
- 0037393778
- D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234.
- (2003) Acc. Chem. Res. , vol.36 , pp. 234
- Culkin, D.A.¹ Hartwig, J.F.²

7
- 0032481653
- J. Åhman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 1918
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1918
- Åhman, J.¹ Wolfe, J.P.² Troutman, M.V.³ Palucki, M.⁴ Buchwald, S.L.⁵

8
- 38349078282
- X. Liao, Z. Weng, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 195
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 195
- Liao, X.¹ Weng, Z.² Hartwig, J.F.³

9
- 0037138675
- T. Hamada, A. Chieffi, J. Åhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1261
- Hamada, T.¹ Chieffi, A.² Åhman, J.³ Buchwald, S.L.⁴

10
- 33645023302
- G. Chen, F. Y. Kwong, H. O. Chan, W.-Y. Yu, A. S. C. Chan, Chem. Commun. 2006, 1413
- (2006) Chem. Commun. , pp. 1413
- Chen, G.¹ Kwong, F.Y.² Chan, H.O.³ Yu, W.-Y.⁴ Chan, A.S.C.⁵

11
- 80054748846
- S. Ge, J. F. Hartwig, J. Am. Chem. Soc. 2011, 133, 16330.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16330
- Ge, S.¹ Hartwig, J.F.²

12
- 73349095157
- J. García-Fortanet, S. L. Buchwald, Angew. Chem. 2008, 120, 8228
- (2008) Angew. Chem. , vol.120 , pp. 8228
- García-Fortanet, J.¹ Buchwald, S.L.²

13
- 54049148627
- Angew. Chem. Int. Ed. 2008, 47, 8108
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8108

14
- 84866932111
- P. Nareddy, L. Mantilli, L. Guénée, C. Mazet, Angew. Chem. 2012, 124, 3892
- (2012) Angew. Chem. , vol.124 , pp. 3892
- Nareddy, P.¹ Mantilli, L.² Guénée, L.³ Mazet, C.⁴

15
- 84859748126
- Angew. Chem. Int. Ed. 2012, 51, 3826.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3826

16
- 67651210439
- A. M. Taylor, R. A. Altman, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 9900
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9900
- Taylor, A.M.¹ Altman, R.A.² Buchwald, S.L.³

17
- 0035906503
- S. Lee, J. F. Hartwig, J. Org. Chem. 2001, 66, 3402.
- (2001) J. Org. Chem. , vol.66 , pp. 3402
- Lee, S.¹ Hartwig, J.F.²

18
- 0037051609
- D. J. Spielvogel, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 3500.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 3500
- Spielvogel, D.J.¹ Buchwald, S.L.²

19
- 79953035867
- A. E. Allen, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 4260
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 4260
- Allen, A.E.¹ Macmillan, D.W.C.²

20
- 80052330954
- J. S. Harvey, S. P. Simonovich, C. R. Jamison, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 13782
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 13782
- Harvey, J.S.¹ Simonovich, S.P.² Jamison, C.R.³ Macmillan, D.W.C.⁴

21
- 80052328305
- A. Bigot, A. E. Williamson, M. J. Gaunt, J. Am. Chem. Soc. 2011, 133, 13778
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 13778
- Bigot, A.¹ Williamson, A.E.² Gaunt, M.J.³

22
- 84861879619
- E. Skucas, D. W. C. MacMillan, J. Am. Chem. Soc. 2012, 134, 9090.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 9090
- Skucas, E.¹ Macmillan, D.W.C.²

23
- 80053492633
- Z. Huang, Z. Liu, J. Zhou, J. Am. Chem. Soc. 2011, 133, 15882.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 15882
- Huang, Z.¹ Liu, Z.² Zhou, J.³

24
- 4243794106
- E. Santaniello, P. Ferraboschi, P. Grisenti, A. Manzocchi, Chem. Rev. 1992, 92, 1071
- (1992) Chem. Rev. , vol.92 , pp. 1071
- Santaniello, E.¹ Ferraboschi, P.² Grisenti, P.³ Manzocchi, A.⁴

25
- 0000760617
- F. Theil, Chem. Rev. 1995, 95, 2203
- (1995) Chem. Rev. , vol.95 , pp. 2203
- Theil, F.¹

26
- 0141532310
- H. Pellissier, Tetrahedron 2003, 59, 8291
- (2003) Tetrahedron , vol.59 , pp. 8291
- Pellissier, H.¹

27
- 78649364101
- references therein
- T. Fischer, J. Pietruszka, Top. Curr. Chem. 2010, 297, 1, and references therein
- (2010) Top. Curr. Chem. , vol.297 , pp. 1
- Fischer, T.¹ Pietruszka, J.²

28
- 39749093400
- references therein
- R. N. Patel, Coord. Chem. Rev. 2008, 252, 659, and references therein.
- (2008) Coord. Chem. Rev. , vol.252 , pp. 659
- Patel, R.N.¹

29
- 0035861011
- Y. Chen, L. Deng, J. Am. Chem. Soc. 2001, 123, 11302
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 11302
- Chen, Y.¹ Deng, L.²

30
- 0000321590
- C. Bolm, G. Schlingloff, K. Weickhardt, Angew. Chem. 1994, 106, 1944
- (1994) Angew. Chem. , vol.106 , pp. 1944
- Bolm, C.¹ Schlingloff, G.² Weickhardt, K.³

31
- 33748234514
- Angew. Chem. Int. Ed. Engl. 1994, 33, 1848
- (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1848

32
- 38149000603
- F. Hollmann, A. Taglieber, F. Schulz, M. T. Reetz, Angew. Chem. 2007, 119, 2961
- (2007) Angew. Chem. , vol.119 , pp. 2961
- Hollmann, F.¹ Taglieber, A.² Schulz, F.³ Reetz, M.T.⁴

33
- 34347247296
- Angew. Chem. Int. Ed. 2007, 46, 2903.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 2903

34
- 69249201073
- Review
- Review:, J. T. Mohr, A. Y. Hong, B. M. Stoltz, Nat. Chem. 2009, 1, 359
- (2009) Nat. Chem. , vol.1 , pp. 359
- Mohr, J.T.¹ Hong, A.Y.² Stoltz, B.M.³

35
- 84867562360
- M. P. Carroll, H. Muller-Bunz, P. J. Guiry, Chem. Commun. 2012, 48, 11142
- (2012) Chem. Commun. , vol.48 , pp. 11142
- Carroll, M.P.¹ Muller-Bunz, H.² Guiry, P.J.³

36
- 47749084742
- C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 9246
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9246
- Cheon, C.H.¹ Yamamoto, H.²

37
- 80052083175
- C. H. Cheon, O. Kanno, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 13248
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 13248
- Cheon, C.H.¹ Kanno, O.² Toste, F.D.³

38
- 34848848323
- A. Yanagisawa, T. Touge, T. Arai, Angew. Chem. 2005, 117, 1570
- (2005) Angew. Chem. , vol.117 , pp. 1570
- Yanagisawa, A.¹ Touge, T.² Arai, T.³

39
- 16244391157
- Angew. Chem. Int. Ed. 2005, 44, 1546
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1546

40
- 80051688161
- E. M. Beck, A. M. Hyde, E. N. Jacobsen, Org. Lett. 2011, 13, 4260.
- (2011) Org. Lett. , vol.13 , pp. 4260
- Beck, E.M.¹ Hyde, A.M.² Jacobsen, E.N.³

41
- 84887321120
- SHELXL 93/97, Programs for Crystal Structure Refinement, University of Göttingen, Germany, 1993 / 1997
- G.M. Sheldrick, SHELXL 93/97, Programs for Crystal Structure Refinement, University of Göttingen, Germany, 1993 / 1997. "Generally speaking, a single phosphorus or heavier atom suffices to determine an absolute structure using Cu-K(alpha)radiation, and with accurate high-resolution low-temperature data including Friedel opposites such an atom may even suffice for Mo-K(alpha)"
- Generally Speaking, A Single Phosphorus or Heavier Atom Suffices to Determine An Absolute Structure Using Cu-K(alpha)radiation, and with Accurate High-resolution Low-temperature Data Including Friedel Opposites Such An Atom May even Suffice for Mo-K(alpha)
- Sheldrick, G.M.¹

42
- 43249092579
- H. D. Flack, G. Bernardinelli, Chirality 2008, 20, 681.
- (2008) Chirality , vol.20 , pp. 681
- Flack, H.D.¹ Bernardinelli, G.²

43
- 79952147387
- Asymmetric synthesis of arylkainic acids using rhodium-catalyzed carbene insertion (for details of the synthetic route, see the Supporting Information on page S2)
- Asymmetric synthesis of arylkainic acids using rhodium-catalyzed carbene insertion (for details of the synthetic route, see the Supporting Information on page S2):, T. Higashi, Y. Isobe, H. Ouchi, H. Suzuki, Y. Okazaki, T. Asakawa, T. Furuta, T. Wakimoto, T. Kan, Org. Lett. 2011, 13, 1089.
- (2011) Org. Lett. , vol.13 , pp. 1089
- Higashi, T.¹ Isobe, Y.² Ouchi, H.³ Suzuki, H.⁴ Okazaki, Y.⁵ Asakawa, T.⁶ Furuta, T.⁷ Wakimoto, T.⁸ Kan, T.⁹

44
- 0025188087
- K. Hashimoto, M. Horikawa, H. Shirahama, Tetrahedron Lett. 1990, 31, 7047.
- (1990) Tetrahedron Lett. , vol.31 , pp. 7047
- Hashimoto, K.¹ Horikawa, M.² Shirahama, H.³

45
- 0019770897
- U. Hacksell, L. E. Arvidsson, U. Svensson, J. L. G. Nilsson, D. Sanchez, H. Wikstroem, P. Lindberg, S. Hjorth, A. Carlsson, J. Med. Chem. 1981, 24, 1475
- (1981) J. Med. Chem. , vol.24 , pp. 1475
- Hacksell, U.¹ Arvidsson, L.E.² Svensson, U.³ Nilsson, J.L.G.⁴ Sanchez, D.⁵ Wikstroem, H.⁶ Lindberg, P.⁷ Hjorth, S.⁸ Carlsson, A.⁹

46
- 0027934781
- C. Sonesson, C.-H. Lin, L. Hansson, N. Waters, K. Svensson, A. Carlsson, M. W. Smith, H. Wikstrom, J. Med. Chem. 1994, 37, 2735
- (1994) J. Med. Chem. , vol.37 , pp. 2735
- Sonesson, C.¹ Lin, C.-H.² Hansson, L.³ Waters, N.⁴ Svensson, K.⁵ Carlsson, A.⁶ Smith, M.W.⁷ Wikstrom, H.⁸

47
- 0029155711
- L. O. Hansson, N. Waters, S. Holm, C. Sonesson, J. Med. Chem. 1995, 38, 3121.
- (1995) J. Med. Chem. , vol.38 , pp. 3121
- Hansson, L.O.¹ Waters, N.² Holm, S.³ Sonesson, C.⁴

48
- 0035905052
- P.-Q. Huang, X. Zheng, X.-M. Deng, Tetrahedron Lett. 2001, 42, 9039.
- (2001) Tetrahedron Lett. , vol.42 , pp. 9039
- Huang, P.-Q.¹ Zheng, X.² Deng, X.-M.³

49
- 33746895149
- A. Pasternak, D. Marino, P. P. Vicario, J. M. Ayala, M. A. Cascierri, W. Parsons, S. G. Mills, M. MacCoss, L. Yang, J. Med. Chem. 2006, 49, 4801.
- (2006) J. Med. Chem. , vol.49 , pp. 4801
- Pasternak, A.¹ Marino, D.² Vicario, P.P.³ Ayala, J.M.⁴ Cascierri, M.A.⁵ Parsons, W.⁶ Mills, S.G.⁷ Maccoss, M.⁸ Yang, L.⁹

50
- 54149105742
- S.-B. Yang, F.-F. Gan, G.-J. Chen, P.-F. Xu, Synlett 2008, 2532.
- (2008) Synlett , pp. 2532
- Yang, S.-B.¹ Gan, F.-F.² Chen, G.-J.³ Xu, P.-F.⁴

51
- 0037768557
- P. Kočovský, Š. Vyskočil, I. Císařová, J. Sejbal, I. Tišlerová, M. Smrčina, G. C. Lloyd-Jones, S. C. Stephen, C. P. Butts, M. Murray, V. Langer, J. Am. Chem. Soc. 1999, 121, 7714
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 7714
- Kočovský, P.¹ Vyskočil, Š.² Císař ová, I.³ Sejbal, J.⁴ Tišlerová, I.⁵ Smrčina, M.⁶ Lloyd-Jones, G.C.⁷ Stephen, S.C.⁸ Butts, C.P.⁹ Murray, M.¹⁰ Langer, V.¹¹

52
- 0037138687
- J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1162
- Yin, J.¹ Rainka, M.P.² Zhang, X.-X.³ Buchwald, S.L.⁴

53
- 0348252349
- P. Dotta, P. G. A. Kumar, P. S. Pregosin, A. Albinati, S. Rizzato, Organometallics 2003, 22, 5345
- (2003) Organometallics , vol.22 , pp. 5345
- Dotta, P.¹ Kumar, P.G.A.² Pregosin, P.S.³ Albinati, A.⁴ Rizzato, S.⁵

54
- 4544372693
- S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907
- (2004) Angew. Chem. , vol.116 , pp. 1907
- Walker, S.D.¹ Barder, T.E.² Martinelli, J.R.³ Buchwald, S.L.⁴

55
- 3042654141
- Angew. Chem. Int. Ed. 2004, 43, 1871.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1871

56
- 81755182712
- A previous computational study reported direct C-C reductive elimination from Oenolates using a Josiphos ligand. No details of the calculation was given
- A previous computational study reported direct C-C reductive elimination from Oenolates using a Josiphos ligand. No details of the calculation was given:, K. Kobayashi, Y. Yamamoto, N. Miyaura, Organometallics 2011, 30, 6323.
- (2011) Organometallics , vol.30 , pp. 6323
- Kobayashi, K.¹ Yamamoto, Y.² Miyaura, N.³

57
- 0000216832
- G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441
- (1996) Acc. Chem. Res. , vol.29 , pp. 441
- Desiraju, G.R.¹

58
- 0346055206
- S. J. Grabowski, J. Phys. Org. Chem. 2004, 17, 18
- (2004) J. Phys. Org. Chem. , vol.17 , pp. 18
- Grabowski, S.J.¹

59
- 0002915748
- T. Steiner, Angew. Chem. 2002, 114, 50
- (2002) Angew. Chem. , vol.114 , pp. 50
- Steiner, T.¹

60
- 33746278019
- Angew. Chem. Int. Ed. 2002, 41, 48
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 48

61
- 0031081961
- M. C. Wahl, M. Sundaralingam, Trends Biochem. Sci. 1997, 22, 97
- (1997) Trends Biochem. Sci. , vol.22 , pp. 97
- Wahl, M.C.¹ Sundaralingam, M.²

62
- 3042533519
- R. K. Castellano, Curr. Org. Chem. 2004, 8, 845
- (2004) Curr. Org. Chem. , vol.8 , pp. 845
- Castellano, R.K.¹

63
- 37849045152
- V. Nanda, A. Schmiedekamp, Proteins Struct. Funct. Bioinf. 2008, 70, 489
- (2008) Proteins Struct. Funct. Bioinf. , vol.70 , pp. 489
- Nanda, V.¹ Schmiedekamp, A.²

64
- 0034679011
- R. Vargas, J. Garza, D. A. Dixon, B. P. Hay, J. Am. Chem. Soc. 2000, 122, 4750.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4750
- Vargas, R.¹ Garza, J.² Dixon, D.A.³ Hay, B.P.⁴

65
- 33644554472
- Arene CH×××O hydrogen bonding was implicated for controlling the E/Z ratio in Wittig reactions of triphenylphosphine ylides
- Arene CH×××O hydrogen bonding was implicated for controlling the E/Z ratio in Wittig reactions of triphenylphosphine ylides:, R. L. Robiette, J. Richardson, V. K. Aggarwal, J. N. Harvey, J. Am. Chem. Soc. 2006, 128, 2394.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2394
- Robiette, R.L.¹ Richardson, J.² Aggarwal, V.K.³ Harvey, J.N.⁴

66
- 0035822774
- E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321
- (2001) Chem. Commun. , pp. 1321
- Corey, E.J.¹ Lee, T.W.²

67
- 34447559627
- H. Yamamoto, Tetrahedron 2007, 63, 8377
- (2007) Tetrahedron , vol.63 , pp. 8377
- Yamamoto, H.¹

68
- 60849101360
- M. N. Paddon-Row, C. D. Anderson, K. N. Houk, J. Org. Chem. 2009, 74, 861
- (2009) J. Org. Chem. , vol.74 , pp. 861
- Paddon-Row, M.N.¹ Anderson, C.D.² Houk, K.N.³

69
- 79960969206
- T. S. Thakur, M. T. Kirchner, D. Bläser, R. Boese, G. R. Desiraju, Phys. Chem. Chem. Phys. 2011, 13, 14076.
- (2011) Phys. Chem. Chem. Phys. , vol.13 , pp. 14076
- Thakur, T.S.¹ Kirchner, M.T.² Bläser, D.³ Boese, R.⁴ Desiraju, G.R.⁵

70
- 0038514123
- D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 6388
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 6388
- Ryu, D.H.¹ Corey, E.J.²

71
- 17644414916
- D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 5384
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 5384
- Ryu, D.H.¹ Corey, E.J.²

72
- 79951965435
- N. Y. M. Omar, N. A. Rahman, S. M. Zain, Bull. Chem. Soc. Jpn. 2011, 84, 196.
- (2011) Bull. Chem. Soc. Jpn. , vol.84 , pp. 196
- Omar, N.Y.M.¹ Rahman, N.A.² Zain, S.M.³

73
- 25844432337
- J. Solà, A. Riera, X. Verdaguer, M. A. Maestro, J. Am. Chem. Soc. 2005, 127, 13629.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 13629
- Solà, J.¹ Riera, A.² Verdaguer, X.³ Maestro, M.A.⁴

74
- 77952359180
- DFT calculations revealed CH×××O interactions between the phosphine methide CH bonds and the ketone carbonyl:, and
- DFT calculations revealed CH×××O interactions between the phosphine methide CH bonds and the ketone carbonyl:, S. L. Shi, L. W. Xu, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 6638 and
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6638
- Shi, S.L.¹ Xu, L.W.² Oisaki, K.³ Kanai, M.⁴ Shibasaki, M.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.