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Volumn 61, Issue 39, 2005, Pages 9349-9355

Automated batch scale-up of microwave-promoted Suzuki and Heck coupling reactions in water using ultra-low metal catalyst concentrations

(3) Arvela, Riina K a Leadbeater, Nicholas E a Collins Jr , Michael J b

a UNIVERSITY OF CONNECTICUT (United States)

b CEM Microwave Technology (United States)

Author keywords

Microwave; Suzuki; Water

Indexed keywords

ARTICLE; AUTOMATION; CATALYSIS; CATALYST; HECK REACTION; MICROWAVE RADIATION; PRIORITY JOURNAL; SCALE UP; SUZUKI REACTION;

EID: 23944509440 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/j.tet.2005.07.063 Document Type: Article

Times cited : (103)

References (62)

1
- 21744447389
- R. Gedye, F. Smith, K. Westaway, H. Ali, L. Baldisera, L. Laberge, and J. Rousell Tetrahedron Lett. 27 1986 279 282
- (1986) Tetrahedron Lett. , vol.27 , pp. 279-282
- Gedye, R.¹ Smith, F.² Westaway, K.³ Ali, H.⁴ Baldisera, L.⁵ Laberge, L.⁶ Rousell, J.⁷

2
- 40949144305
- R.J. Giguere, T.L. Bray, S.M. Duncan, and G. Majetich Tetrahedron Lett. 27 1986 4945 4948
- (1986) Tetrahedron Lett. , vol.27 , pp. 4945-4948
- Giguere, R.J.¹ Bray, T.L.² Duncan, S.M.³ Majetich, G.⁴

3
- 0141878086
- Blackwell Oxford
- A number of books on microwave-promoted synthesis have been published recently: (a) P. Lidström J.P. Tierney Microwave-Assisted Organic Synthesis 2004 Blackwell Oxford
- (2004) Microwave-Assisted Organic Synthesis
- Lidström, P.¹ Tierney, J.P.²

4
- 0011932271
- Wiley-VCH Weinheim
- A. Loupy Microwaves in Organic Synthesis 2002 Wiley-VCH Weinheim
- (2002) Microwaves in Organic Synthesis
- Loupy, A.¹

5
- 0012106816
- CEM Matthews NC
- B.L. Hayes Microwave Synthesis: Chemistry at the Speed of Light 2002 CEM Matthews NC
- (2002) Microwave Synthesis: Chemistry at the Speed of Light
- Hayes, B.L.¹

6
- 11144325118
- For a recent review see: C.O. Kappe Angew Chem., Int. Ed. 43 2004 6250 6284
- (2004) Angew Chem., Int. Ed. , vol.43 , pp. 6250-6284
- Kappe, C.O.¹

7
- 0035813244
- For other reviews on the general area of microwave-promoted organic synthesis see: (a) P. Lidström, J.P. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225 9283
- (2001) Tetrahedron , vol.57 , pp. 9225-9283
- Lidström, P.¹ Tierney, J.P.² Wathey, B.³ Westman, J.⁴

8
- 0029078472
- S. Caddick Tetrahedron 51 1995 10403 10432
- (1995) Tetrahedron , vol.51 , pp. 10403-10432
- Caddick, S.¹

9
- 14544289090
- R.K. Arvela, and N.E. Leadbeater J. Org. Chem. 70 2005 1786 1790
- (2005) J. Org. Chem. , vol.70 , pp. 1786-1790
- Arvela, R.K.¹ Leadbeater, N.E.²

10
- 11844268057
- R.K. Arvela, N.E. Leadbeater, M.S. Sangi, V.A. Williams, P. Granados, and R.S. Singer J. Org. Chem. 70 2005 161 168
- (2005) J. Org. Chem. , vol.70 , pp. 161-168
- Arvela, R.K.¹ Leadbeater, N.E.² Sangi, M.S.³ Williams, V.A.⁴ Granados, P.⁵ Singer, R.S.⁶

11
- 0004252595
- Blackie London
- For a general introduction to organic synthesis in water see: (a) P.A. Grieco Organic Synthesis in Water 1997 Blackie London
- (1997) Organic Synthesis in Water
- Grieco, P.A.¹

12
- 0003602022
- Kluwer Dordrecht
- C.-J. Li, and T.H. Chan Organic Reactions in Aqueous Media 1997 Kluwer Dordrecht
- (1997) Organic Reactions in Aqueous Media
- Li, C.-J.¹ Chan, T.H.²

13
- 0037361038
- For examples of post-reaction palladium removal strategies see: (a) Y. Urawa, M. Miyazawa, N. Ozeki, and K. Ogura Org. Process Res. Dev. 7 2003 191 195
- (2003) Org. Process Res. Dev. , vol.7 , pp. 191-195
- Urawa, Y.¹ Miyazawa, M.² Ozeki, N.³ Ogura, K.⁴

14
- 0031504362
- V.W. Rosso, D.A. Lust, P.J. Bernot, J.A. Grosso, S.P. Modi, A. Rusowicz, T.C. Sedergran, J.H. Simpson, S.K. Srivastava, M.J. Humora, and N.G. Anderson Org. Process Res. Dev. 1 1997 311 314
- (1997) Org. Process Res. Dev. , vol.1 , pp. 311-314
- Rosso, V.W.¹ Lust, D.A.² Bernot, P.J.³ Grosso, J.A.⁴ Modi, S.P.⁵ Rusowicz, A.⁶ Sedergran, T.C.⁷ Simpson, J.H.⁸ Srivastava, S.K.⁹ Humora, M.J.¹⁰ Anderson, N.G.¹¹

15
- 0028054343
- R.D. Larsen, A.O. King, C.Y. Chen, E.G. Corley, B.S. Foster, F.E. Roberts, C. Yang, D.R. Lieberman, R.A. Reamer, D.M. Tschaen, T.R. Verhoeven, P.J. Reider, Y.S. Lo, L.T. Rossano, A.S. Brookes, D. Meloni, J.R. Moore, and J.F. Arnett J. Org. Chem. 59 1994 6391 6394
- (1994) J. Org. Chem. , vol.59 , pp. 6391-6394
- Larsen, R.D.¹ King, A.O.² Chen, C.Y.³ Corley, E.G.⁴ Foster, B.S.⁵ Roberts, F.E.⁶ Yang, C.⁷ Lieberman, D.R.⁸ Reamer, R.A.⁹ Tschaen, D.M.¹⁰ Verhoeven, T.R.¹¹ Reider, P.J.¹² Lo, Y.S.¹³ Rossano, L.T.¹⁴ Brookes, A.S.¹⁵ Meloni, D.¹⁶ Moore, J.R.¹⁷ Arnett, J.F.¹⁸

16
- 7644241634
- For recent reviews see: (a) F. Bellina, A. Carpita, and R. Rossi Synthesis 2004 2419 2440
- (2004) Synthesis , pp. 2419-2440
- Bellina, F.¹ Carpita, A.² Rossi, R.³

17
- 0036589259
- J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
- (2002) Chem. Rev. , vol.102 , pp. 1359-1469
- Hassan, J.¹ Sévignon, M.² Gozzi, C.³ Schulz, E.⁴ Lemaire, M.⁵

18
- 0037175592
- S. Kotha, S. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633 9695
- (2002) Tetrahedron , vol.58 , pp. 9633-9695
- Kotha, S.¹ Lahiri, S.² Kashinath, D.³

19
- 0003397781
- F. Diederich P.J. Sting Wiley-VCH Weinheim
- For selected recent reviews of the Heck reaction see: (a) S. Brase, and A. de Meijere F. Diederich P.J. Sting Metal-Catalysed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim Chapter 3
- (1998) Metal-Catalysed Cross-Coupling Reactions
- Brase, S.¹ De Meijere, A.²

20
- 0034249671
- I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
- (2000) Chem. Rev. , vol.100 , pp. 3009-3066
- Beletskaya, I.P.¹ Cheprakov, A.V.²

21
- 0035959456
- N.J. Whitcombe, K.K. Hii, and S.E. Gibson Tetrahedron 57 2001 7449 7476
- (2001) Tetrahedron , vol.57 , pp. 7449-7476
- Whitcombe, N.J.¹ Hii, K.K.² Gibson, S.E.³

22
- 0345732180
- For a general introduction to continuous processing see: (a) G. Jas, and A. Kirschning Chem. Eur. J. 9 2003 5708 5723
- (2003) Chem. Eur. J. , vol.9 , pp. 5708-5723
- Jas, G.¹ Kirschning, A.²

23
- 0035563923
- N.G. Anderson Org. Process Res. Dev. 5 2001 613 621
- (2001) Org. Process Res. Dev. , vol.5 , pp. 613-621
- Anderson, N.G.¹

24
- 33751158531
- T. Cablewski, A.F. Faux, and C.R. Strauss J. Org. Chem. 59 1994 3408 3412
- (1994) J. Org. Chem. , vol.59 , pp. 3408-3412
- Cablewski, T.¹ Faux, A.F.² Strauss, C.R.³

25
- 0037025725
- W.-C. Shieh, S. Dell, and O. Repiĉ Tetrahedron Lett. 43 2002 5607 5609
- (2002) Tetrahedron Lett. , vol.43 , pp. 5607-5609
- Shieh, W.-C.¹ Dell, S.² Repiĉ, O.³

26
- 23944489298
- B.M. Khadlikar, and V.R. Madyar Org. Process Res. Dev. 5 2001 451 452s
- (2001) Org. Process Res. Dev. , vol.5
- Khadlikar, B.M.¹ Madyar, V.R.²

27
- 0034712151
- K. Kazba, B.R. Chapados, J.E. Gestwicki, and J.L. McGrath J. Org. Chem. 65 2000 1210 1214
- (2000) J. Org. Chem. , vol.65 , pp. 1210-1214
- Kazba, K.¹ Chapados, B.R.² Gestwicki, J.E.³ McGrath, J.L.⁴

28
- 0342656971
- E. Esveld, F. Chemat, and J. van Haveren Chem. Eng. Technol. 23 2000 279 283
- (2000) Chem. Eng. Technol. , vol.23 , pp. 279-283
- Esveld, E.¹ Chemat, F.² Van Haveren, J.³

29
- 0034180026
- E. Esveld, F. Chemat, and J. van Haveren Chem. Eng. Technol. 23 2000 429 435
- (2000) Chem. Eng. Technol. , vol.23 , pp. 429-435
- Esveld, E.¹ Chemat, F.² Van Haveren, J.³

30
- 0035904289
- J. Marquié, G. Salmoria, M. Poux, A. Laporterie, J. Dubac, and N. Roques Ind. Eng. Chem. Res. 40 2001 4485 4490
- (2001) Ind. Eng. Chem. Res. , vol.40 , pp. 4485-4490
- Marquié, J.¹ Salmoria, G.² Poux, M.³ Laporterie, A.⁴ Dubac, J.⁵ Roques, N.⁶

31
- 0033627449
- J. Marquié, C. Laporte, A. Laporterie, J. Dubac, and J.-R. Desmurs Ind. Eng. Chem. Res. 39 2000 1124 1131
- (2000) Ind. Eng. Chem. Res. , vol.39 , pp. 1124-1131
- Marquié, J.¹ Laporte, C.² Laporterie, A.³ Dubac, J.⁴ Desmurs, J.-R.⁵

32
- 0035951524
- J. Marquié, A. Laporterie, J. Dubac, J.-R. Desmurs, and N. Roques J. Org. Chem. 66 2001 421 425
- (2001) J. Org. Chem. , vol.66 , pp. 421-425
- Marquié, J.¹ Laporterie, A.² Dubac, J.³ Desmurs, J.-R.⁴ Roques, N.⁵

33
- 3042682172
- N.S. Wilson, C.R. Sarko, and G.P. Roth Org. Process Res. Dev. 8 2004 535 538
- (2004) Org. Process Res. Dev. , vol.8 , pp. 535-538
- Wilson, N.S.¹ Sarko, C.R.² Roth, G.P.³

34
- 3042646131
- For a recent review of micro-reactor technology see: H. Pennemann, P. Watts, S.J. Haswell, V. Hessel, and H. Lowe Org. Process Res. Dev. 8 2004 422 439
- (2004) Org. Process Res. Dev. , vol.8 , pp. 422-439
- Pennemann, H.¹ Watts, P.² Haswell, S.J.³ Hessel, V.⁴ Lowe, H.⁵

35
- 1642503793
- P. He, S.J. Haswell, and P.D.I. Fletcher Lab Chip 4 2004 38 41
- (2004) Lab Chip , vol.4 , pp. 38-41
- He, P.¹ Haswell, S.J.² Fletcher, P.D.I.³

36
- 17744385778
- S.J. Haswell, and P.D.I. Fletcher Appl. Catal. A 274 2004 111 114
- (2004) Appl. Catal. a , vol.274 , pp. 111-114
- Haswell, S.J.¹ Fletcher, P.D.I.²

37
- 11144299620
- M. Karches, H. Takashima, and Y. Kanno Ind. Eng. Chem. Res. 43 2004 8200 8206
- (2004) Ind. Eng. Chem. Res. , vol.43 , pp. 8200-8206
- Karches, M.¹ Takashima, H.² Kanno, Y.³

38
- 0011932271
- A. Loupy Wiley-VCH Weinheim
- C.R. Strauss A. Loupy Microwaves in Organic Synthesis 2002 Wiley-VCH Weinheim 35 60
- (2002) Microwaves in Organic Synthesis , pp. 35-60
- Strauss, C.R.¹

39
- 0001391706
- K.D. Raner, C.R. Strauss, R.W. Trainor, and J.S. Thorn J. Org. Chem. 60 1995 2456 2460
- (1995) J. Org. Chem. , vol.60 , pp. 2456-2460
- Raner, K.D.¹ Strauss, C.R.² Trainor, R.W.³ Thorn, J.S.⁴

40
- 0347635266
- F. Lehmann, P. Pilotti, and K. Luthman Mol. Diversity 7 2003 145 152
- (2003) Mol. Diversity , vol.7 , pp. 145-152
- Lehmann, F.¹ Pilotti, P.² Luthman, K.³

41
- 0037462327
- S.A. Shackelford, M.B. Anderson, L.C. Christie, T. Goetzen, M.C. Guzman, M.A. Hananel, W.D. Kornreich, H. Li, V.P. Pathak, A.K. Rabinovich, R.J. Rajapakse, L.K. Truesdale, S.M. Tsank, and H.N. Vazir J. Org. Chem. 68 2003 267 275
- (2003) J. Org. Chem. , vol.68 , pp. 267-275
- Shackelford, S.A.¹ Anderson, M.B.² Christie, L.C.³ Goetzen, T.⁴ Guzman, M.C.⁵ Hananel, M.A.⁶ Kornreich, W.D.⁷ Li, H.⁸ Pathak, V.P.⁹ Rabinovich, A.K.¹⁰ Rajapakse, R.J.¹¹ Truesdale, L.K.¹² Tsank, S.M.¹³ Vazir, H.N.¹⁴

42
- 0036859616
- B.M. Khadilkar, and G.L. Rebeiro Org. Process Res. Dev. 6 2002 826 828
- (2002) Org. Process Res. Dev. , vol.6 , pp. 826-828
- Khadilkar, B.M.¹ Rebeiro, G.L.²

43
- 0036328070
- J. Fraga-Dubreuil, M.H. Famelart, and J.P. Bazureau Org. Process Res. Dev. 6 2002 374 378
- (2002) Org. Process Res. Dev. , vol.6 , pp. 374-378
- Fraga-Dubreuil, J.¹ Famelart, M.H.² Bazureau, J.P.³

44
- 0034345903
- J. Cleophax, M. Liagre, A. Loupy, and A. Petit Org. Process Res. Dev. 4 2000 498 504
- (2000) Org. Process Res. Dev. , vol.4 , pp. 498-504
- Cleophax, J.¹ Liagre, M.² Loupy, A.³ Petit, A.⁴

45
- 0032355224
- B. Perio, M.-J. Dozias, and J. Hamelin Org. Process Res. Dev. 2 1998 428 430
- (1998) Org. Process Res. Dev. , vol.2 , pp. 428-430
- Perio, B.¹ Dozias, M.-J.² Hamelin, J.³

46
- 0141922655
- A. Stadler, B.H. Yousefi, D. Dallinger, P. Walla, E. Van der Eycken, N. Kaval, and C.O. Kappe Org. Process Res. Dev. 7 2003 707 716
- (2003) Org. Process Res. Dev. , vol.7 , pp. 707-716
- Stadler, A.¹ Yousefi, B.H.² Dallinger, D.³ Walla, P.⁴ Van Der Eycken, E.⁵ Kaval, N.⁶ Kappe, C.O.⁷

47
- 0037090556
- A. Stadler, S. Pichler, G. Horeis, and C.O. Kappe Tetrahedron 58 2002 3177 3183
- (2002) Tetrahedron , vol.58 , pp. 3177-3183
- Stadler, A.¹ Pichler, S.² Horeis, G.³ Kappe, C.O.⁴

48
- 12344277532
- J. Alcázar, G. Diels, and B. Schoentjes QSAR Comb. Sci. 23 2004 906 910
- (2004) QSAR Comb. Sci. , vol.23 , pp. 906-910
- Alcázar, J.¹ Diels, G.² Schoentjes, B.³

49
- 11144357278
- T.E. Jacks, D.T. Belmont, C.A. Briggs, N.M. Horne, G.D. Kanter, G.L. Karrick, J.J. Krikke, R.J. McCabe, J.G. Mustakis, T.N. Nanninga, G.S. Risedorph, R.E. Seamans, R. Skeean, D.D. Winkle, and T.M. Zennie Org. Process Res. Dev. 8 2004 201 212
- (2004) Org. Process Res. Dev. , vol.8 , pp. 201-212
- Jacks, T.E.¹ Belmont, D.T.² Briggs, C.A.³ Horne, N.M.⁴ Kanter, G.D.⁵ Karrick, G.L.⁶ Krikke, J.J.⁷ McCabe, R.J.⁸ Mustakis, J.G.⁹ Nanninga, T.N.¹⁰ Risedorph, G.S.¹¹ Seamans, R.E.¹² Skeean, R.¹³ Winkle, D.D.¹⁴ Zennie, T.M.¹⁵

50
- 0038722891
- M.F. Lipton, M.A. Mauragis, M.T. Maloney, M.F. Veley, D.W. VanderBor, J.J. Newby, R.B. Appell, and E.D. Daugs Org. Process Res. Dev. 7 2003 385 392
- (2003) Org. Process Res. Dev. , vol.7 , pp. 385-392
- Lipton, M.F.¹ Mauragis, M.A.² Maloney, M.T.³ Veley, M.F.⁴ Vanderbor, D.W.⁵ Newby, J.J.⁶ Appell, R.B.⁷ Daugs, E.D.⁸

51
- 0036219578
- Y. Mori, M Nakamura, T. Wakabayash, K. Mori, and S. Kobayashi Synlett 2002 601 603
- (2002) Synlett , pp. 601-603
- Mori, Y.¹ Nakamura, M.² Wakabayash, T.³ Mori, K.⁴ Kobayashi, S.⁵

52
- 33645484732
- D.D. Winkle, and K.M. Schaab Org. Process Res. Dev. 5 2001 50 451
- (2001) Org. Process Res. Dev. , vol.5 , pp. 50-451
- Winkle, D.D.¹ Schaab, K.M.²

53
- 0035533025
- S. Caron, S.S. Massett, D.E. Bogle, M.J. Castaldi, and T.F. Braish Org. Process Res. Dev. 5 2001 254 256
- (2001) Org. Process Res. Dev. , vol.5 , pp. 254-256
- Caron, S.¹ Massett, S.S.² Bogle, D.E.³ Castaldi, M.J.⁴ Braish, T.F.⁵

54
- 0034345892
- T.J.N. Watson, S.W. Horgan, R.S. Shah, R.A. Farr, R.A. Schnettler, C.R. Nevill Jr., F.J. Weiberth, E.W. Huber, B.M. Baron, M.E. Webster, R.K. Mishra, B.L. Harrison, P.L. Nyce, C.L. Rand, and C.T. Goralski Org. Process Res. Dev. 4 2000 477 487
- (2000) Org. Process Res. Dev. , vol.4 , pp. 477-487
- Watson, T.J.N.¹ Horgan, S.W.² Shah, R.S.³ Farr, R.A.⁴ Schnettler, R.A.⁵ Nevill Jr., C.R.⁶ Weiberth, F.J.⁷ Huber, E.W.⁸ Baron, B.M.⁹ Webster, M.E.¹⁰ Mishra, R.K.¹¹ Harrison, B.L.¹² Nyce, P.L.¹³ Rand, C.L.¹⁴ Goralski, C.T.¹⁵

55
- 0033438776
- D.S. Ennis, J. McManus, W. Wood Kaczmar, J. Richardson, G.E. Smith, and A. Carstairs Org. Process Res. Dev. 3 1999 248 252
- (1999) Org. Process Res. Dev. , vol.3 , pp. 248-252
- Ennis, D.S.¹ McManus, J.² Wood Kaczmar, W.³ Richardson, J.⁴ Smith, G.E.⁵ Carstairs, A.⁶

56
- 3042595331
- S. Liu, T. Fukuyama, M. Sato, and I. Ryu Org. Process Res. Dev. 8 2004 477 481
- (2004) Org. Process Res. Dev. , vol.8 , pp. 477-481
- Liu, S.¹ Fukuyama, T.² Sato, M.³ Ryu, I.⁴

57
- 0036859130
- D. Ainge, and L.-M. Vaz Org. Process Res. Dev. 6 2002 811 813
- (2002) Org. Process Res. Dev. , vol.6 , pp. 811-813
- Ainge, D.¹ Vaz, L.-M.²

58
- 0036003916
- J.W. Raggon, and W.M. Snyder Org. Process Res. Dev. 6 2002 67 69
- (2002) Org. Process Res. Dev. , vol.6 , pp. 67-69
- Raggon, J.W.¹ Snyder, W.M.²

59
- 0000249122
- A. Zapf, and M. Beller Top. Catal. 19 2002 101 109
- (2002) Top. Catal. , vol.19 , pp. 101-109
- Zapf, A.¹ Beller, M.²

60
- 0037570115
- F.C. Gorth, M. Rucker, M. Eckhardt, and R. Bruckner Eur. J. Org. Chem. 2000 2605 2611
- (2000) Eur. J. Org. Chem. , pp. 2605-2611
- Gorth, F.C.¹ Rucker, M.² Eckhardt, M.³ Bruckner, R.⁴

61
- 0032366684
- D.C. Waite, and C.P. Mason Org. Process Res. Dev. 2 1998 116 120
- (1998) Org. Process Res. Dev. , vol.2 , pp. 116-120
- Waite, D.C.¹ Mason, C.P.²

62
- 0027131242
- P.R. Bovy, and J.G. Rico Tetrahedron Lett. 34 1993 8015 8018
- (1993) Tetrahedron Lett. , vol.34 , pp. 8015-8018
- Bovy, P.R.¹ Rico, J.G.²

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