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Volumn 18, Issue 21, 2012, Pages 6616-6625

Mechanistic origin of antagonist effects of usual anionic bases (OH -, CO 3 2-) as modulated by their countercations (Na +, Cs +, K +) in palladium-catalyzed Suzuki-Miyaura reactions

(3) Amatore, Christian a Jutand, Anny a Le Duc, Gaëtan a

a ECOLE NORMALE SUPÉRIEURE (France)

Author keywords

anionic bases; arylboronic acid; cations; palladium; reaction mechanisms

Indexed keywords

ANIONIC BASIS; ANTAGONIST EFFECTS; ARYLBORONIC ACIDS; COMMON-BASE; LOW CONCENTRATIONS; N ,N-DIMETHYLFORMAMIDE; PALLADIUM-CATALYZED; PRESENCE OF WATER; REACTION MECHANISM; REDUCTIVE ELIMINATION; SUZUKI-MIYAURA; SUZUKI-MIYAURA REACTION; TRANSMETALATION;

CARBONATES; CHEMICAL REACTIONS; DIMETHYLFORMAMIDE; ORGANIC SOLVENTS; PALLADIUM; POSITIVE IONS;

CESIUM;

EID: 84861110565 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201200516 Document Type: Article

Times cited : (122)

References (47)

1
- 0022334461
- A. Suzuki, Pure Appl. Chem. 1985, 57, 1749-1758
- (1985) Pure Appl. Chem. , vol.57 , pp. 1749-1758
- Suzuki, A.¹

2
- 84943950090
- A. Suzuki, Pure Appl. Chem. 1991, 63, 419-422
- (1991) Pure Appl. Chem. , vol.63 , pp. 419-422
- Suzuki, A.¹

3
- 2042507954
- N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
- (1995) Chem. Rev. , vol.95 , pp. 2457-2483
- Miyaura, N.¹ Suzuki, A.²

4
- 0000975959
- in, JAI Press, London
- N. Miyaura, in Advances in Metal-Organic Synthesis, Vol. 6: Synthesis of Biaryls via the Cross-Coupling Reaction of Arylboronic Acids, JAI Press, London, 1998, pp. 187-243
- (1998) Advances in Metal-Organic Synthesis, Vol. 6: Synthesis of Biaryls Via the Cross-Coupling Reaction of Arylboronic Acids , pp. 187-243
- Miyaura, N.¹

5
- 0346786657
- A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168
- (1999) J. Organomet. Chem. , vol.576 , pp. 147-168
- Suzuki, A.¹

6
- 0036643464
- N. Miyaura, J. Organomet. Chem. 2002, 653, 54-57
- (2002) J. Organomet. Chem. , vol.653 , pp. 54-57
- Miyaura, N.¹

7
- 39749179066
- F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron 2008, 64, 3047-3101
- (2008) Tetrahedron , vol.64 , pp. 3047-3101
- Alonso, F.¹ Beletskaya, I.P.² Yus, M.³

8
- 77954811401
- G. A. Molander, Angew. Chem. 2009, 121, 9404-9425
- (2009) Angew. Chem. , vol.121 , pp. 9404-9425
- Molander, G.A.¹

9
- 72949108920
- Angew. Chem. Int. Ed. 2009, 48, 9240-9261
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9240-9261

10
- 78650664109
- A. J. J. Lennox, G. C. Lloyd-Jones, Isr. J. Chem. 2010, 50, 664-674
- (2010) Isr. J. Chem. , vol.50 , pp. 664-674
- Lennox, A.J.J.¹ Lloyd-Jones, G.C.²

11
- 85039397112
- For a screening of bases and solvents, see
- For a screening of bases and solvents, see:, T. Watanabe, N. Miyaura, A. Suzuki, Synlett 1992, 207-210
- (1992) Synlett , pp. 207-210
- Watanabe, T.¹ Miyaura, N.² Suzuki, A.³

12
- 0029874643
- P. D. Hobbs, V. Upender, J. Liu, D. J. Pollart, D. W. Thomas, M. I. Dawson, Chem. Commun. 1996, 923-924
- (1996) Chem. Commun. , pp. 923-924
- Hobbs, P.D.¹ Upender, V.² Liu, J.³ Pollart, D.J.⁴ Thomas, D.W.⁵ Dawson, M.I.⁶

13
- 79955586117
- C. Liu, Q. Ni, F. Bao, J. Qiu, Green Chem. 2011, 13, 1260-1266.
- (2011) Green Chem. , vol.13 , pp. 1260-1266
- Liu, C.¹ Ni, Q.² Bao, F.³ Qiu, J.⁴

14
- 22844434133
- K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563
- (2005) Angew. Chem. , vol.117 , pp. 4516-4563
- Nicolaou, K.C.¹ Bulger, P.G.² Sarlah, D.³

15
- 22744442306
- Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4442-4489

16
- 79951662418
- C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2011, 17, 2492-2503.
- (2011) Chem. Eur. J. , vol.17 , pp. 2492-2503
- Amatore, C.¹ Jutand, A.² Le Duc, G.³

17
- 79951832916
- B. P. Carrow, J. F. Hartwig, J. Am. Chem. Soc. 2011, 133, 2116-42119
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 2116-42119
- Carrow, B.P.¹ Hartwig, J.F.²

18
- 80053492922
- 2 on imine-palladacycle-OH, see
- 2 on imine-palladacycle-OH, see:, J. L. Serrano, L. García, J. Pérez, E. Pérez, J. García, G. Sánchez, P. Sehnal, S. De Ornellas, T. J. Williams, I. J. S. Fairlamb, Organometallics 2011, 30, 5095-5109.
- (2011) Organometallics , vol.30 , pp. 5095-5109
- Serrano, J.L.¹ García, L.² Pérez, J.³ Pérez, E.⁴ García, J.⁵ Sánchez, G.⁶ Sehnal, P.⁷ De Ornellas, S.⁸ Williams, T.J.⁹ Fairlamb, I.J.S.¹⁰

19
- 84861112253
- C. Amatore, A. Jutand, G. Le Duc, Angew. Chem. 2012, 124, 1408-1411
- (2012) Angew. Chem. , vol.124 , pp. 1408-1411
- Amatore, C.¹ Jutand, A.² Le Duc, G.³

20
- 84856491163
- Angew. Chem. Int. Ed. 2012, 51, 1379-1382.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1379-1382

21
- 0035945027
- R. A. Batey, T. D. Quach, Tetrahedron Lett. 2001, 42, 9099-9103
- (2001) Tetrahedron Lett. , vol.42 , pp. 9099-9103
- Batey, R.A.¹ Quach, T.D.²

22
- 0035825767
- G. A. Molander, T. Ito, Org. Lett. 2001, 3, 393-396
- (2001) Org. Lett. , vol.3 , pp. 393-396
- Molander, G.A.¹ Ito, T.²

23
- 0001660117
- G. A. Molander, B. Biolatto, Org. Lett. 2002, 4, 1867-1870
- (2002) Org. Lett. , vol.4 , pp. 1867-1870
- Molander, G.A.¹ Biolatto, B.²

24
- 0038362703
- G. A. Molander, B. Biolatto, J. Org. Chem. 2003, 68, 4302-4314
- (2003) J. Org. Chem. , vol.68 , pp. 4302-4314
- Molander, G.A.¹ Biolatto, B.²

25
- 26844560825
- A. K. L. Yuen, C. A. Hutton, Tetrahedron Lett. 2005, 46, 7899-7903
- (2005) Tetrahedron Lett. , vol.46 , pp. 7899-7903
- Yuen, A.K.L.¹ Hutton, C.A.²

26
- 79956071393
- M. Butters, J. N. Harvey, J. Jover, A. J. J. Lennox, G. C. Lloyd-Jones, P. M. Murray, Angew. Chem. 2010, 122, 5282-5286
- (2010) Angew. Chem. , vol.122 , pp. 5282-5286
- Butters, M.¹ Harvey, J.N.² Jover, J.³ Lennox, A.J.J.⁴ Lloyd-Jones, G.C.⁵ Murray, P.M.⁶

27
- 77954846356
- Angew. Chem. Int. Ed. 2010, 49, 5156-5160.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5156-5160

28
- 33845281635
- J.-I. Uenishi, J.-M. Beau, R. W. Armstrong, Y. Kishi, J. Am. Chem. Soc. 1987, 109, 4756-4758
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 4756-4758
- Uenishi, J.-I.¹ Beau, J.-M.² Armstrong, R.W.³ Kishi, Y.⁴

29
- 0034710467
- S. A. Frank, H. Chen, R. K. Kunz, M. J. Schnaderbeck, W. R. Roush, Org. Lett. 2000, 2, 2691-2694
- (2000) Org. Lett. , vol.2 , pp. 2691-2694
- Frank, S.A.¹ Chen, H.² Kunz, R.K.³ Schnaderbeck, M.J.⁴ Roush, W.R.⁵

30
- 0242330782
- D. A. Evans, J. T. Starr, J. Am. Chem. Soc. 2003, 125, 13531-13540
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 13531-13540
- Evans, D.A.¹ Starr, J.T.²

31
- 0042135971
- D. A. Evans, J. T. Starr, Angew. Chem. 2002, 114, 1865-1868
- (2002) Angew. Chem. , vol.114 , pp. 1865-1868
- Evans, D.A.¹ Starr, J.T.²

32
- 0036260285
- Angew. Chem. Int. Ed. 2002, 41, 1787-1790.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1787-1790

33
- 49149125488
- For the elucidation of the mechanism of catalytic reactions by means of electrochemistry, see
- For the elucidation of the mechanism of catalytic reactions by means of electrochemistry, see:, A. Jutand, Chem. Rev. 2008, 108, 2300-2347.
- (2008) Chem. Rev. , vol.108 , pp. 2300-2347
- Jutand, A.¹

34
- 0003764465
- Wiley, New York
- B. E. Douglas, D. H. N. McDaniel, J. J. Alexander, Concepts and Models of Inorganic Chemistry, Wiley, New York, 1994
- (1994) Concepts and Models of Inorganic Chemistry
- Douglas, B.E.¹ McDaniel, D.H.N.² Alexander, J.J.³

35
- 0003125762
- L. Ma, F. M. Siu, C. W. Tsang, Chem. Phys. Lett. 2000, 322, 65-72.
- (2000) Chem. Phys. Lett. , vol.322 , pp. 65-72
- Ma, L.¹ Siu, F.M.² Tsang, C.W.³

36
- 84947151032
- N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513-519
- (1981) Synth. Commun. , vol.11 , pp. 513-519
- Miyaura, N.¹ Yanagi, T.² Suzuki, A.³

37
- 0000795317
- G. B. Smith, G. C. Dezeny, D. L. Hughes, A. O. King, T. R. Verhoeven, J. Org. Chem. 1994, 59, 8151-8156
- (1994) J. Org. Chem. , vol.59 , pp. 8151-8156
- Smith, G.B.¹ Dezeny, G.C.² Hughes, D.L.³ King, A.O.⁴ Verhoeven, T.R.⁵

38
- 84961981202
- C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6829-6836
- Adamo, C.¹ Amatore, C.² Ciofini, I.³ Jutand, A.⁴ Lakmini, H.⁵

39
- 0034127063
- II species, see
- II species, see:, C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321
- (2000) Acc. Chem. Res. , vol.33 , pp. 314-321
- Amatore, C.¹ Jutand, A.²

40
- 0032483724
- 10 complexes, see:, and
- 10 complexes, see:, R. Giovannini, P. Knochel, J. Am. Chem. Soc. 1998, 120, 11186-11187 and
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11186-11187
- Giovannini, R.¹ Knochel, P.²

41
- 84856453425
- G. Jarvis, I. J. S. Fairlamb, Curr. Org. Chem. 2011, 15, 3175-3196.
- (2011) Curr. Org. Chem. , vol.15 , pp. 3175-3196
- Jarvis, G.¹ Fairlamb, I.J.S.²

42
- 4344665807
- C. Meyers, B. U. W. Maes, K. T. J. Loones, G. Bal, G. L. F. Lemière, R. A. Dommisse, J. Org. Chem. 2004, 69, 6010-6017.
- (2004) J. Org. Chem. , vol.69 , pp. 6010-6017
- Meyers, C.¹ Maes, B.U.W.² Loones, K.T.J.³ Bal, G.⁴ Lemière, G.L.F.⁵ Dommisse, R.A.⁶

43
- 0000852316
- C. Amatore, A. Jutand, M. A. M'Barki, Organometallics 1992, 11, 3009-3013
- (1992) Organometallics , vol.11 , pp. 3009-3013
- Amatore, C.¹ Jutand, A.² M'Barki, M.A.³

44
- 0001589134
- X/OAc=0.3 (X=I), 0.10 (X=Br), 0.04 (X=Cl) in DMF at 27 °C
- X/OAc=0.3 (X=I), 0.10 (X=Br), 0.04 (X=Cl) in DMF at 27 °C.
- (1995) Organometallics , vol.14 , pp. 5605-5614
- Amatore, C.¹ Carré, E.² Jutand, A.³ M'Barki, M.A.⁴ Meyer, G.⁵

45
- 33745520399
- E. Ferrer Flegeau, M. E. Popkin, M. F. Greaney, Org. Lett. 2006, 8, 2495-2498.
- (2006) Org. Lett. , vol.8 , pp. 2495-2498
- Ferrer Flegeau, E.¹ Popkin, M.E.² Greaney, M.F.³

46
- 78650301260
- G. A. Molander, S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc. 2010, 132, 17701-17703
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 17701-17703
- Molander, G.A.¹ Trice, S.L.J.² Dreher, S.D.³

47
- 80052131662
- 2O, see
- 2O, see:, A. F. Schmidt, A. A. Kurokhtina, E. V. Larina, Russ. J. Gen. Chem. 2011, 81, 1573-1574
- (2011) Russ. J. Gen. Chem. , vol.81 , pp. 1573-1574
- Schmidt, A.F.¹ Kurokhtina, A.A.² Larina, E.V.³

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