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Volumn 15, Issue 15, 2009, Pages 3823-3829

Acceleration of reductive elimination of [Ar-Pd-Csp3] by a phosphine/electron-deficient olefin ligand: A kinetic investigation

(11) Zhang, Heng a Luo, Xiancai a Wongkhan, Kittiya b Duan, Hui a Li, Qiang a Zhu, Lizheng a Wang, Jian c Batsanov, Andrei S b Howard, Judith A K b Marder, Todd B b Lei, Aiwen a,d

a WUHAN UNIVERSITY (China)

b DURHAM UNIVERSITY (United Kingdom)

c Real Time Analytics (United States)

d SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Cross coupling; Kinetics; Olefins; Palladium; Reductive elimination

Indexed keywords

C-C DOUBLE BONDS; CATALYTIC ACTIVITIES; CROSS-COUPLING; ELECTRON-DEFICIENT OLEFINS; FIRST ORDERS; HOMOGENEOUS CATALYSIS; HYDRIDE ELIMINATIONS; HYDROGEN ATOMS; KINETIC INVESTIGATIONS; NEGISHI COUPLINGS; NEGISHI CROSS COUPLINGS; OLEFIN LIGANDS; ORDERS OF MAGNITUDES; PD COMPLEXES; PD NANOPARTICLES; REDUCTIVE ELIMINATION; SELECTIVE CATALYSTS; TURN-OVER FREQUENCIES; TURN-OVER NUMBERS;

BENZENE; BENZENE REFINING; CATALYSIS; CHLORINE COMPOUNDS; HYDROGEN; LIGANDS; OLEFINS; PALLADIUM COMPOUNDS; RATE CONSTANTS; REACTION KINETICS;

PALLADIUM;

EID: 63849273180 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.200802209 Document Type: Article

Times cited : (48)

References (55)

1
- 0003397781
- 2nd ed, Wiley-VCH, Weinheim
- F. Diederich, P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004.
- (2004) Metal-Catalyzed Cross-Coupling Reactions
- Diederich, F.¹ Stang, P.J.²

2
- 0003995267
- Wiley, New York
- E.-i. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley, New York, 2002.
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis
- Negishi, E.-I.¹

3
- 0000571094
- D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203;
- (1999) Angew. Chem , vol.111 , pp. 3201-3203
- Cárdenas, D.J.¹

4
- 0040164574
- Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
- (1999) Angew. Chem. Int. Ed , vol.38 , pp. 3018-3020

5
- 3042657024
- D. J. Cárdenas, Angew. Chem. 2003, 115, 398-401;
- (2003) Angew. Chem , vol.115 , pp. 398-401
- Cárdenas, D.J.¹

6
- 0037468071
- Angew. Chem. Int. Ed. 2003, 42, 384-387.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 384-387

7
- 0034249479
- T.-Y. Luh, M.-k. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204.
- (2000) Chem. Rev , vol.100 , pp. 3187-3204
- Luh, T.-Y.¹ Leung, M.-K.² Wong, K.-T.³

8
- 3142689000
- D. A. Culkin, J. F. Hartwig, Organometallics 2004, 23, 3398-3416.
- (2004) Organometallics , vol.23 , pp. 3398-3416
- Culkin, D.A.¹ Hartwig, J.F.²

9
- 33947680107
- J. A. Casares, P. Espinet, B. Fuentes, G. Salas, J. Am. Chem. Soc. 2007, 129, 3508-3509.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 3508-3509
- Casares, J.A.¹ Espinet, P.² Fuentes, B.³ Salas, G.⁴

10
- 0037047555
- N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566.
- (2002) J. Org. Chem , vol.67 , pp. 5553-5566
- Kataoka, N.¹ Shelby, Q.² Stambuli, J.P.³ Hartwig, J.F.⁴

11
- 0032560932
- D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 9722-9723
- Old, D.W.¹ Wolfe, J.P.² Buchwald, S.L.³

12
- 1842717280
- G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818-3821;
- (2003) Angew. Chem , vol.115 , pp. 3818-3821
- Altenhoff, G.¹ Goddard, R.² Lehmann, C.W.³ Glorius, F.⁴

13
- 0042969355
- Angew. Chem. Int. Ed. 2003, 42, 3690-3693.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3690-3693

14
- 0345802559
- O. Navarro, R. A. Kelly III, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194-16195.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 16194-16195
- Navarro, O.¹ Kelly III, R.A.² Nolan, S.P.³

15
- 0242407300
- M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 13642-13643.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 13642-13643
- Eckhardt, M.¹ Fu, G.C.²

16
- 5644254180
- J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc. 2004, 126, 13028-13032.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 13028-13032
- Milne, J.E.¹ Buchwald, S.L.²

17
- 0032578172
- Chem. Soc. 1.998
- B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1.998, 120, 7369-7370.
- J. Am , vol.120 , pp. 7369-7370
- Hamann, B.C.¹ Hartwig, J.F.²

18
- 0033534423
- A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10-11.
- (1999) J. Org. Chem , vol.64 , pp. 10-11
- Littke, A.F.¹ Fu, G.C.²

19
- 0034812321
- C. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719-2724.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 2719-2724
- Dai, C.¹ Fu, G.C.²

20
- 24044441578
- N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Org. Lett. 2005, 7, 3805-3807.
- (2005) Org. Lett , vol.7 , pp. 3805-3807
- Hadei, N.¹ Kantchev, E.A.B.² O'Brien, C.J.³ Organ, M.G.⁴

21
- 0013319981
- A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386;
- (2002) Angew. Chem , vol.114 , pp. 4350-4386
- Littke, A.F.¹ Fu, G.C.²

22
- 0037112673
- Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 4176-4211

23
- 0000460761
- A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1967, 89, 5989-5990.
- (1967) J. Am. Chem. Soc , vol.89 , pp. 5989-5990
- Yamamoto, A.¹ Ikeda, S.²

24
- 33947291257
- T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359.
- (1971) J. Am. Chem. Soc , vol.93 , pp. 3350-3359
- Yamamoto, T.¹ Yamamoto, A.² Ikeda, S.³

25
- 0001244413
- R. Sustmann, J. Lau, Chem. Ber. 1986, 119, 2531-2541,
- (1986) Chem. Ber , vol.119 , pp. 2531-2541
- Sustmann, R.¹ Lau, J.²

26
- 0037059492
- A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79-85.
- (2002) J. Org. Chem , vol.67 , pp. 79-85
- Jensen, A.E.¹ Knochel, P.²

27
- 0036388663
- T. Yamamoto, M. AbIa, Y. Murakami, Bull. Chem. Soc. Jpn. 2002, 75, 1997-2009.
- (2002) Bull. Chem. Soc. Jpn , vol.75 , pp. 1997-2009
- Yamamoto, T.¹ AbIa, M.² Murakami, Y.³

28
- 0000221759
- R. Giovannini, T. Studemann, G. Dussin, P. Knochel, Angew. Chem. 1998, 110, 2512-2515;
- (1998) Angew. Chem , vol.110 , pp. 2512-2515
- Giovannini, R.¹ Studemann, T.² Dussin, G.³ Knochel, P.⁴

29
- 0345404157
- Angew. Chem, Int. Ed. 1998, 37, 2387-2390.
- (1998) Angew. Chem, Int. Ed , vol.37 , pp. 2387-2390

30
- 0032927129
- R. Giovannini, T. Stuedemann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem, 1999, 64, 3544-3553.
- (1999) J. Org. Chem , vol.64 , pp. 3544-3553
- Giovannini, R.¹ Stuedemann, T.² Devasagayaraj, A.³ Dussin, G.⁴ Knochel, P.⁵

31
- 21344470856
- M. A. Grundl, J. J. Kennedy-Smith, D. Trauner, Organometallics 2005, 24, 2831-2833.
- (2005) Organometallics , vol.24 , pp. 2831-2833
- Grundl, M.A.¹ Kennedy-Smith, J.J.² Trauner, D.³

32
- 24344504544
- A. Scrivanti, V. Beghetto, U. Matteoli, S. Antonaroli, A. Marini, B. Crociani, Tetrahedron 2005, 61, 9752-9758.
- (2005) Tetrahedron , vol.61 , pp. 9752-9758
- Scrivanti, A.¹ Beghetto, V.² Matteoli, U.³ Antonaroli, S.⁴ Marini, A.⁵ Crociani, B.⁶

33
- 33846077486
- D. B. G. Williams, M. L. Shaw, Tetrahedron 2007, 63, 1624-1629.
- (2007) Tetrahedron , vol.63 , pp. 1624-1629
- Williams, D.B.G.¹ Shaw, M.L.²

34
- 33845228401
- I. J. S. Fairlamb, A. R. Kapdi, A. F. Lee, G. P. McGlacken, F. Weissburger, A. H. M. de Vries, L. Schmieder-van de Vondervoort, Chem. Eur. J. 2006, 12, 8750- 8761.
- (2006) Chem. Eur. J , vol.12 , pp. 8750-8761
- Fairlamb, I.J.S.¹ Kapdi, A.R.² Lee, A.F.³ McGlacken, G.P.⁴ Weissburger, F.⁵ de Vries, A.H.M.⁶ Schmieder-van de Vondervoort, L.⁷

35
- 10144222904
- I. J. S. Fairlamb, A.R. Kapdi, A.F. Lee, Org. Lett. 2004, 6, 4435-4438.
- (2004) Org. Lett , vol.6 , pp. 4435-4438
- Fairlamb, I.J.S.¹ Kapdi, A.R.² Lee, A.F.³

36
- 33645887524
- Y. Mace, A. R. Kapdi, I. J. S. Fairlamb, A. Jutand, Organometallics 2006, 25, 1795-1800.
- (2006) Organometallics , vol.25 , pp. 1795-1800
- Mace, Y.¹ Kapdi, A.R.² Fairlamb, I.J.S.³ Jutand, A.⁴

37
- 53549088307
- I. J. S. Fairlamb, Org. Biomol. Chem. 2008, 6, 3645-3656.
- (2008) Org. Biomol. Chem , vol.6 , pp. 3645-3656
- Fairlamb, I.J.S.¹

38
- 63049121670
- P. S. Pregosin, Chem. Commun. 2008, 4875-4884.
- (2008) Chem. Commun , pp. 4875-4884
- Pregosin, P.S.¹

39
- 35948988432
- X. Luo, H. Zhang, H. Duan, Q. Liu, L. Zhu, T. Zhang, A. Lei, Org. Lett. 2007, 9, 4571-4574.
- (2007) Org. Lett , vol.9 , pp. 4571-4574
- Luo, X.¹ Zhang, H.² Duan, H.³ Liu, Q.⁴ Zhu, L.⁵ Zhang, T.⁶ Lei, A.⁷

40
- 63849324902
- CCDC 701728 (3) and 701729 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via 3: C54H42Cl 2O2P2PdCH2Cl2, Mr=1131.97, T= 120 K, monoclinic, space group P21/n, a, 9.0882(8, b=25.761(2, c= 11.379(1) Å, β= 106.49(1)°, V=2554.4(4) Å3, Z=2, ρcalcd= 1.472 g cm-3, μ= 0.78 mm-1, 34743 reflections with 20=60°, 7423 unique, Rint=0.033, R(F)=0.040 [6286 data with I=Iσ(I, wR(F2)=0.113 all data, Crystal data for 4: C54H42O2P 2Pd·0.5 CH2Cl2
- 2) = 0.065 (all data).

41
- 4043062197
- M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 1559-1563.
- (2004) Chem. Commun , pp. 1559-1563
- Reetz, M.T.¹ de Vries, J.G.²

42
- 37249037855
- I. J. S. Fairlamb, S. Grant, P. McCormack, J. Whittall, Dalton Trans. 2007, 859-865.
- (2007) Dalton Trans , pp. 859-865
- Fairlamb, I.J.S.¹ Grant, S.² McCormack, P.³ Whittall, J.⁴

43
- 0032787242
- G. P. F. Van Strijdonck, M. D. K. Boele, P. C. J. Kamer, J. G. de Vries, P. W. N. M. Van Leeuwen, Eur. J. Inorg. Chem. 1999, 1073-1076.
- (1999) Eur. J. Inorg. Chem , pp. 1073-1076
- Van Strijdonck, G.P.F.¹ Boele, M.D.K.² Kamer, P.C.J.³ de Vries, J.G.⁴ Van Leeuwen, P.W.N.M.⁵

44
- 33846213170
- I. J. S. .Fairlamb, R. J. K. Taylor, J. L. Serrano, G. Sanchez, New J. Chem. 2006, 30, 1695-1704.
- I. J. S. .Fairlamb, R. J. K. Taylor, J. L. Serrano, G. Sanchez, New J. Chem. 2006, 30, 1695-1704.

45
- 0141856236
- A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285-3288.
- (2003) Org. Lett , vol.5 , pp. 3285-3288
- de Vries, A.H.M.¹ Mulders, J.M.C.A.² Mommers, J.H.M.³ Henderickx, H.J.W.⁴ de Vries, J.G.⁵

46
- 63849134091
- While Pd NPs are also known to be effective catalysts for this transformation,[42] both the clear first-order dependence on [Pd] and the results of PPh3 inhibition experiments (see text and Supporting Information for details) ruled them out as being active species in the present case
- 3 inhibition experiments (see text and Supporting Information for details) ruled them out as being active species in the present case.

47
- 55249103938
- J. Liu, Y. Deng, H. Wang, H. Zhang, G. Yu, H. Zhang, Q. Li, T. B. Marder, Z. Yang, A. Lei, Org. Lett. 2008, 10, 2661-2664.
- (2008) Org. Lett , vol.10 , pp. 2661-2664
- Liu, J.¹ Deng, Y.² Wang, H.³ Zhang, H.⁴ Yu, G.⁵ Zhang, H.⁶ Li, Q.⁷ Marder, T.B.⁸ Yang, Z.⁹ Lei, A.¹⁰

48
- 33745506850
- J. S. Mathew, M. Klussmann, H. Iwamura, F. Valera, A. Futran, E. A. C. Emanuelsson, D. G. Blackmond, J. Org. Chem. 2006, 71, 4711-4722.
- (2006) J. Org. Chem , vol.71 , pp. 4711-4722
- Mathew, J.S.¹ Klussmann, M.² Iwamura, H.³ Valera, F.⁴ Futran, A.⁵ Emanuelsson, E.A.C.⁶ Blackmond, D.G.⁷

49
- 33746248151
- D. G. Blackmond, Angew. Chem. 2005, 117, 4374-4393;
- (2005) Angew. Chem , vol.117 , pp. 4374-4393
- Blackmond, D.G.¹

50
- 22744443220
- Angew. Chem. Int. Ed. 2005, 44, 4302-4320.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4302-4320

51
- 63849331920
- Hartwig reported reductive elimination involving an electronic-rich aryl group, and Espinet employed an electron-poor aryl group. Although the substrates in our system, which involved an electronpoor aryl group, were different from theirs, the data still indicate the dramatic accelerating effect on reductive elimination
- Hartwig reported reductive elimination involving an electronic-rich aryl group, and Espinet employed an electron-poor aryl group. Although the substrates in our system, which involved an electronpoor aryl group, were different from theirs, the data still indicate the dramatic accelerating effect on reductive elimination.

52
- 2342604431
- G. Rothenberg, S. C. Cruz, G. P. F. Van Strijdonck, H.C.J. Hoefsloot, Adv. Synth. Catal. 2004, 346, 467-473.
- (2004) Adv. Synth. Catal , vol.346 , pp. 467-473
- Rothenberg, G.¹ Cruz, S.C.² Van Strijdonck, G.P.F.³ Hoefsloot, H.C.J.⁴

53
- 24144481245
- C. S. Consorti, F. R. Flores, J. Dupont, J. Am. Chem. Soc. 2005, 127, 12054-12065.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 12054-12065
- Consorti, C.S.¹ Flores, F.R.² Dupont, J.³

54
- 0029902679
- P. Kuzmic, Anal. Biochem. 1996, 237, 260-273.
- (1996) Anal. Biochem , vol.237 , pp. 260-273
- Kuzmic, P.¹

55
- 55549097483
- W. Shi, Y. Luo, X. Luo, L. Chao, H. Zhang, J. Wang, A. Lei, J. Am. Chem. Soc. 2008, 130, 14713-14720.
- (2008) J. Am. Chem. Soc , vol.130 , pp. 14713-14720
- Shi, W.¹ Luo, Y.² Luo, X.³ Chao, L.⁴ Zhang, H.⁵ Wang, J.⁶ Lei, A.⁷

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