SCOPUS 정보 검색 플랫폼

Chemical Science

Volumn 1, Issue 3, 2010, Pages 331-336

Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate

(4) Yeung, Charles S a Zhao, Xiaodan a Borduas, Nadine a Dong, Vy M a

a UNIVERSITY OF TORONTO (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDES; ARYLATIONS; BENZAMIDES; C-C BONDS; C-H BOND; CROSS-COUPLINGS; ELECTRON-RICH; FUNCTIONALIZATIONS; OPTIMIZED REACTION CONDITIONS; PD COMPLEX; REACTION CONDITIONS; SODIUM PERSULFATE; STOICHIOMETRIC REACTIVITY;

AMIDES; CATALYSIS; PALLADIUM COMPOUNDS; SODIUM; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

EID: 78650663537 PISSN: 20416520 EISSN: 20416539 Source Type: Journal
DOI: 10.1039/c0sc00231c Document Type: Article

Times cited : (195)

References (64)

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

2
- 33747071481
- For examples of oxidative cross-coupling involving twofold C-H functionalization, see
- J.-P. Corbet G. Mignani Chem. Rev. 2006 106 2651
- (2006) Chem. Rev. , vol.106 , pp. 2651
- Corbet, J.-P.¹ Mignani, G.²

3
- 34249936878
- D. R. Stuart K. Fagnou Science 2007 316 1172
- (2007) Science , vol.316 , pp. 1172
- Stuart, D.R.¹ Fagnou, K.²

4
- 35048815950
- D. R. Stuart E. Villemure K. Fagnou J. Am. Chem. Soc. 2007 129 12072
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12072
- Stuart, D.R.¹ Villemure, E.² Fagnou, K.³

5
- 34848899222
- K. L. Hull M. S. Sanford J. Am. Chem. Soc. 2007 129 11904
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 11904
- Hull, K.L.¹ Sanford, M.S.²

6
- 67650495369
- K. L. Hull M. S. Sanford J. Am. Chem. Soc. 2009 131 9651
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9651
- Hull, K.L.¹ Sanford, M.S.²

7
- 38849126856
- B.-J. Li S.-L. Tian Z. Fang Z.-J. Shi Angew. Chem., Int. Ed. 2008 47 1115
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1115
- Li, B.-J.¹ Tian, S.-L.² Fang, Z.³ Shi, Z.-J.⁴

8
- 48749125749
- G. Brasche J. García-Fortanet S. L. Buchwald Org. Lett. 2008 10 2207
- (2008) Org. Lett. , vol.10 , pp. 2207
- Brasche, G.¹ García-Fortanet, J.² Buchwald, S.L.³

9
- 47749125841
- S. H. Cho S. J. Hwang S. Chang J. Am. Chem. Soc. 2008 130 9254
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9254
- Cho, S.H.¹ Hwang, S.J.² Chang, S.³

10
- 34547960227
- T. A. Dwight N. R. Rue D. Charyk R. Josselyn B. DeBoef Org. Lett. 2007 9 3137
- (2007) Org. Lett. , vol.9 , pp. 3137
- Dwight, T.A.¹ Rue, N.R.² Charyk, D.³ Josselyn, R.⁴ Deboef, B.⁵

11
- 43449139728
- S. Potavathri A. S. Dumas T. A. Dwight G. R. Naumiec J. M. Hammann B. DeBoef Tetrahedron Lett. 2008 49 4050
- (2008) Tetrahedron Lett. , vol.49 , pp. 4050
- Potavathri, S.¹ Dumas, A.S.² Dwight, T.A.³ Naumiec, G.R.⁴ Hammann, J.M.⁵ Deboef, B.⁶

12
- 34948824004
- J.-B. Xia S.-L. You Organometallics 2007 26 4869
- (2007) Organometallics , vol.26 , pp. 4869
- Xia, J.-B.¹ You, S.-L.²

13
- 33846396118
- For a review on other oxidative couplings, see
- R. Li L. Jiang W. Lu Organometallics 2006 25 5973
- (2006) Organometallics , vol.25 , pp. 5973
- Li, R.¹ Jiang, L.² Lu, W.³

14
- 75749099888
- For reviews on direct arylation, see
- J. A. Ashenhurst Chem. Soc. Rev. 2010 39 540
- (2010) Chem. Soc. Rev. , vol.39 , pp. 540
- Ashenhurst, J.A.¹

15
- 33846918696
- D. Alberico M. E. Scott M. Lautens Chem. Rev. 2007 107 174
- (2007) Chem. Rev. , vol.107 , pp. 174
- Alberico, D.¹ Scott, M.E.² Lautens, M.³

16
- 42949122199
- B.-J. Li S.-D. Yang Z.-J. Shi Synlett 2008 949
- (2008) Synlett , pp. 949
- Li, B.-J.¹ Yang, S.-D.² Shi, Z.-J.³

17
- 72449170089
- L. Ackermann R. Vicente A. R. Kapdi Angew. Chem., Int. Ed. 2009 48 9792
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 9792
- Ackermann, L.¹ Vicente, R.² Kapdi, A.R.³

18
- 69249101991
- G. P. McGlacken L. M. Batemann Chem. Soc. Rev. 2009 38 2447
- (2009) Chem. Soc. Rev. , vol.38 , pp. 2447
- McGlacken, G.P.¹ Batemann, L.M.²

19
- 77952579093
- For examples of C-H functionalization of phenylacetic acid derivatives, see
- X. Zhao C. S. Yeung V. M. Dong J. Am. Chem. Soc. 2010 132 5837
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 5837
- Zhao, X.¹ Yeung, C.S.² Dong, V.M.³

20
- 58849130239
- D.-H. Wang T.-S. Mei J.-Q. Yu J. Am. Chem. Soc. 2008 130 17676
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 17676
- Wang, D.-H.¹ Mei, T.-S.² Yu, J.-Q.³

21
- 54849420705
- R. Giri J.-Q. Yu J. Am. Chem. Soc. 2008 130 14082
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14082
- Giri, R.¹ Yu, J.-Q.²

22
- 54849436434
- For selected accounts on the bioactivity of phenylacetic acid derivatives, see
- M. Wasa J.-Q. Yu J. Am. Chem. Soc. 2008 130 14058
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14058
- Wasa, M.¹ Yu, J.-Q.²

23
- 0028802943
- W. R. Hudgins S. Shack C. E. Myers D. Samid Biochem. Pharmacol. 1995 50 1273
- (1995) Biochem. Pharmacol. , vol.50 , pp. 1273
- Hudgins, W.R.¹ Shack, S.² Myers, C.E.³ Samid, D.⁴

24
- 0028356445
- H. Martínez-Blanco A. Reglero J. M. Luengo J. Ind. Microbiol. 1994 13 144
- (1994) J. Ind. Microbiol. , vol.13 , pp. 144
- Martínez-Blanco, H.¹ Reglero, A.² Luengo, J.M.³

25
- 84982375981
- V. K. Chamberlain R. L. Wain Ann. Appl. Biol. 1971 69 65
- (1971) Ann. Appl. Biol. , vol.69 , pp. 65
- Chamberlain, V.K.¹ Wain, R.L.²

26
- 0014150513
- For phenylacetamide derivatives, see
- R. M. Muir T. Fujita C. Hansch Plant Physiol. 1967 42 1519
- (1967) Plant Physiol. , vol.42 , pp. 1519
- Muir, R.M.¹ Fujita, T.² Hansch, C.³

27
- 0011705796
- J. G. Samaritoni L. Arndt T. J. Bruce J. E. Dripps J. Gifford C. J. Hatton W. H. Hendrix J. R. Schoonover G. W. Johnson V. B. Hegde S. Thornburgh J. Agric. Food Chem. 1997 45 1920
- (1997) J. Agric. Food Chem. , vol.45 , pp. 1920
- Samaritoni, J.G.¹ Arndt, L.² Bruce, T.J.³ Dripps, J.E.⁴ Gifford, J.⁵ Hatton, C.J.⁶ Hendrix, W.H.⁷ Schoonover, J.R.⁸ Johnson, G.W.⁹ Hegde, V.B.¹⁰ Thornburgh, S.¹¹

28
- 0019138436
- For a review on directed ortho-metallation, see
- P. K. Yonan R. L. Novotney C. M. Woo K. A. Prodan F. M. Hershenson J. Med. Chem. 1980 23 1102
- (1980) J. Med. Chem. , vol.23 , pp. 1102
- Yonan, P.K.¹ Novotney, R.L.² Woo, C.M.³ Prodan, K.A.⁴ Hershenson, F.M.⁵

29
- 0000385213
- TFA facilitates formation of Pd(ii) σ-aryl intermediates from direct electrophilic palladation of benzene; our results suggest that TFA can also promote directing group assisted C-H bond functionalizations by cyclopalladation. See
- M. P. Sibi V. Snieckus J. Org. Chem. 1983 48 1935
- (1983) J. Org. Chem. , vol.48 , pp. 1935
- Sibi, M.P.¹ Snieckus, V.²

30
- 0034677867
- Ref. 2k 2-Arylacetamides bearing no free N-H bonds, such as 2-phenyl-1-(pyrrolidin-1-yl)ethanone (1r), did not undergo the desired oxidative arylation For examples of C-H functionalization of benzamides, see
- C. Jia D. Piao J. Oyamada W. Lu T. Kitamura Y. Fujiwara Science 2000 287 1992
- (2000) Science , vol.287 , pp. 1992
- Jia, C.¹ Piao, D.² Oyamada, J.³ Lu, W.⁴ Kitamura, T.⁵ Fujiwara, Y.⁶

31
- 0034620911
- Y. Kametani T. Satoh M. Miura M. Nomura Tetrahedron Lett. 2000 41 2655
- (2000) Tetrahedron Lett. , vol.41 , pp. 2655
- Kametani, Y.¹ Satoh, T.² Miura, M.³ Nomura, M.⁴

32
- 33750309483
- For examples of intramolecular oxidative arylations, see
- D. Shabashov O. Daugulis Org. Lett. 2006 8 4947
- (2006) Org. Lett. , vol.8 , pp. 4947
- Shabashov, D.¹ Daugulis, O.²

33
- 46849109148
- B. Liégault D. Lee M. P. Huestis D. R. Stuart K. Fagnou J. Org. Chem. 2008 73 5022
- (2008) J. Org. Chem. , vol.73 , pp. 5022
- Liégault, B.¹ Lee, D.² Huestis, M.P.³ Stuart, D.R.⁴ Fagnou, K.⁵

34
- 67649576709
- T. Watanabe S. Oishi N. Fujii H. Ohno J. Org. Chem. 2009 74 4720
- (2009) J. Org. Chem. , vol.74 , pp. 4720
- Watanabe, T.¹ Oishi, S.² Fujii, N.³ Ohno, H.⁴

35
- 70349227133
- V. Sridharan M. A. Martín J. C. Menéndez Eur. J. Org. Chem. 2009 4614
- (2009) Eur. J. Org. Chem. , pp. 4614
- Sridharan, V.¹ Martín, M.A.² Menéndez, J.C.³

36
- 0032818056
- Ref. 2h For a review on palladacycles, see
- H. Hagelin J. D. Oslob B. Åkermark Chem.-Eur. J. 1999 5 2413
- (1999) Chem.-Eur. J. , vol.5 , pp. 2413
- Hagelin, H.¹ Oslob, J.D.² Åkermark, B.³

37
- 21944441002
- N-Arylbenzamides bearing free N-H bonds, such as N-phenylbenzamide (1aa), did not undergo the desired oxidative arylation. The presence of an OMe group on the anilide portion was not tolerated, in contrast to the efficient phenylation of 1m (Table 3, entry 10, 99%) For reports on isolation of N-methylcrinasiadine (2ad), see
- J. Dupont C. S. Consorti J. Spencer Chem. Rev. 2005 105 2527
- (2005) Chem. Rev. , vol.105 , pp. 2527
- Dupont, J.¹ Consorti, C.S.² Spencer, J.³

38
- 0029008603
- W. Doepke H. P. Lam E. Gruendemann M. Bartoszek S. Flatau Pharmazie 1995 50 511
- (1995) Pharmazie , vol.50 , pp. 511
- Doepke, W.¹ Lam, H.P.² Gruendemann, E.³ Bartoszek, M.⁴ Flatau, S.⁵

39
- 0001405535
- For total syntheses of N-methylcrinasiadine (2ad), see
- R. Suau A. I. Gómez R. Rico Phytochemistry 1990 29 1710
- (1990) Phytochemistry , vol.29 , pp. 1710
- Suau, R.¹ Gómez, A.I.² Rico, R.³

40
- 33846077515
- R. Sanz Y. Fernandez M. P. Castroviejo A. Perez F. J. Fananas Eur. J. Org. Chem. 2007 62
- (2007) Eur. J. Org. Chem. , pp. 62
- Sanz, R.¹ Fernandez, Y.² Castroviejo, M.P.³ Perez, A.⁴ Fananas, F.J.⁵

41
- 36148956710
- G. Cahiez A. Moyeux J. Buendia C. Duplais J. Am. Chem. Soc. 2007 129 13788
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 13788
- Cahiez, G.¹ Moyeux, A.² Buendia, J.³ Duplais, C.⁴

42
- 23244438907
- T. Harayama Y. Kawata C. Nagura T. Sato T. Miyagoe H. Abe Y. Takeuchi Tetrahedron Lett. 2005 46 6091
- (2005) Tetrahedron Lett. , vol.46 , pp. 6091
- Harayama, T.¹ Kawata, Y.² Nagura, C.³ Sato, T.⁴ Miyagoe, T.⁵ Abe, H.⁶ Takeuchi, Y.⁷

43
- 19544373479
- G. Cahiez C. Chaboche F. Mahuteau-Betzer M. Ahr Org. Lett. 2005 7 1943
- (2005) Org. Lett. , vol.7 , pp. 1943
- Cahiez, G.¹ Chaboche, C.² Mahuteau-Betzer, F.³ Ahr, M.⁴

44
- 37049067873
- M. G. Banwell B. D. Bissett S. Busato C. J. Cowden D. C. R. Hockless J. W. Holman R. W. Read A. W. Wu J. Chem. Soc., Chem. Commun. 1995 2551
- (1995) J. Chem. Soc., Chem. Commun. , pp. 2551
- Banwell, M.G.¹ Bissett, B.D.² Busato, S.³ Cowden, C.J.⁴ Hockless, D.C.R.⁵ Holman, J.W.⁶ Read, R.W.⁷ Wu, A.W.⁸

45
- 0000983917
- M. G. Banwell C. J. Cowden Aust. J. Chem. 1994 47 2235
- (1994) Aust. J. Chem. , vol.47 , pp. 2235
- Banwell, M.G.¹ Cowden, C.J.²

46
- 0025880852
- W. R. Bowman H. Heaney B. M. Jordan Tetrahedron 1991 47 10119
- (1991) Tetrahedron , vol.47 , pp. 10119
- Bowman, W.R.¹ Heaney, H.² Jordan, B.M.³

47
- 37049097406
- J. Grimshaw R. Hamilton J. Trocha-Grimshaw J. Chem. Soc., Perkin Trans. 1 1982 229
- (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 229
- Grimshaw, J.¹ Hamilton, R.² Trocha-Grimshaw, J.³

48
- 0017863106
- R. K.-Y. Zee-Cheng S.-J. Yan C. C. Cheng J. Med. Chem. 1978 21 199
- (1978) J. Med. Chem. , vol.21 , pp. 199
- Zee-Cheng, R.K.-Y.¹ Yan, S.-J.² Cheng, C.C.³

49
- 84984158911
- A. Mondon K. Krohn Chem. Ber. 1972 105 3726
- (1972) Chem. Ber. , vol.105 , pp. 3726
- Mondon, A.¹ Krohn, K.²

50
- 37049169132
- The internuclear distance between the two Pd atoms in was determined to be 2.9233(9) Å and 2.9515(9) Å for the two independent molecules in the asymmetric unit, while for 3b, the bond distance was 2.8779(5) Å. In comparison to other Pd complexes bearing bridging trifluoroacetate ligands, our bimetallic Pd complex 3 exhibits slightly shorter Pd-Pd bonds
- H. S. Forrest R. D. Haworth A. R. Pinder T. S. Stevens J. Chem. Soc. 1949 1311
- (1949) J. Chem. Soc. , vol.3 , pp. 1311
- Forrest, H.S.¹ Haworth, R.D.² Pinder, A.R.³ Stevens, T.S.⁴

51
- 1842739324
- P. L. Ruddock D. J. Williams P. B. Reese Steroids 2004 69 193
- (2004) Steroids , vol.69 , pp. 193
- Ruddock, P.L.¹ Williams, D.J.² Reese, P.B.³

52
- 0142186856
- T. A. Stromnova D. V. Paschenko L. I. Boganova M. V. Daineko S. B. Katser A. V. Chukarov L. G. Kuz'mina J. A. K. Howard Inorg. Chim. Acta 2003 350 283
- (2003) Inorg. Chim. Acta , vol.350 , pp. 283
- Stromnova, T.A.¹ Paschenko, D.V.² Boganova, L.I.³ Daineko, M.V.⁴ Katser, S.B.⁵ Chukarov, A.V.⁶ Kuz'Mina, L.G.⁷ Howard, J.A.K.⁸

53
- 0034733075
- I. Schwarz J. Rust C. W. Lehmann M. Braun J. Organomet. Chem. 2000 605 109
- (2000) J. Organomet. Chem. , vol.605 , pp. 109
- Schwarz, I.¹ Rust, J.² Lehmann, C.W.³ Braun, M.⁴

54
- 0001901617
- For a Pd·TFA complex exhibiting a similar Pd-Pd bond distance, see: Ref. 4
- R. Goddard C. Krüger R. Mynott M. Neumann G. Wilke J. Organomet. Chem. 1993 454 C20
- (1993) J. Organomet. Chem. , vol.454 , pp. 20
- Goddard, R.¹ Krüger, C.² Mynott, R.³ Neumann, M.⁴ Wilke, G.⁵

55
- 0034347116
- T. A. Stromnova S. T. Orlova D. N. Kazyul'kin I. P. Stolyarov I. L. Eremenko Russ. Chem. Bull. 2000 49 150
- (2000) Russ. Chem. Bull. , vol.49 , pp. 150
- Stromnova, T.A.¹ Orlova, S.T.² Kazyul'Kin, D.N.³ Stolyarov, I.P.⁴ Eremenko, I.L.⁵

56
- 35648976608
- For seminal work on high oxidation state bimetallic Pd species, see
- P. K. Killian C. J. Bruell C. Liang M. C. Marley Soil Sediment Contam. 2007 16 523
- (2007) Soil Sediment Contam. , vol.16 , pp. 523
- Killian, P.K.¹ Bruell, C.J.² Liang, C.³ Marley, M.C.⁴

57
- 67949109328
- D. C. Powers T. Ritter Nat. Chem. 2009 1 302
- (2009) Nat. Chem. , vol.1 , pp. 302
- Powers, D.C.¹ Ritter, T.²

58
- 72249115788
- D. C. Powers M. A. L. Geibel J. E. M. N. Klein T. Ritter J. Am. Chem. Soc. 2009 131 17050
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 17050
- Powers, D.C.¹ Geibel, M.A.L.² Klein, J.E.M.N.³ Ritter, T.⁴

59
- 68249136644
- For a review on Pd(ii/iv) catalysis, see
- N. R. Deprez M. S. Sanford J. Am. Chem. Soc. 2009 131 11234
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 11234
- Deprez, N.R.¹ Sanford, M.S.²

60
- 75749111062
- L.-M. Xu B.-J. Li Z. Yang Z.-J. Shi Chem. Soc. Rev. 2010 39 712
- (2010) Chem. Soc. Rev. , vol.39 , pp. 712
- Xu, L.-M.¹ Li, B.-J.² Yang, Z.³ Shi, Z.-J.⁴

61
- 33646456189
- L. V. Desai H. A. Malik M. S. Sanford Org. Lett. 2006 8 1141
- (2006) Org. Lett. , vol.8 , pp. 1141
- Desai, L.V.¹ Malik, H.A.² Sanford, M.S.³

62
- 45249095830
- G.-W. Wang T.-T. Yuan X.-L. Wu J. Org. Chem. 2008 73 4717
- (2008) J. Org. Chem. , vol.73 , pp. 4717
- Wang, G.-W.¹ Yuan, T.-T.² Wu, X.-L.³

63
- 67650507268
- C. F. Rosewall P. A. Sibbald D. V. Liskin F. E. Michael J. Am. Chem. Soc. 2009 131 9488
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9488
- Rosewall, C.F.¹ Sibbald, P.A.² Liskin, D.V.³ Michael, F.E.⁴

64
- 70350662846
- P. A. Sibbald C. F. Rosewall R. D. Swartz F. E. Michael J. Am. Chem. Soc. 2009 131 15945
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 15945
- Sibbald, P.A.¹ Rosewall, C.F.² Swartz, R.D.³ Michael, F.E.⁴

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