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Volumn , Issue 44, 2008, Pages 5779-5781

Rhodium(I)-catalyzed one-pot synthesis of dialkyl ketones from methanol and alkenes through directed sp3 C-H bond activation of N-methylamine

(3) Jo, Eun Ae a Lee, Ji Hyun a Jun, Chul Ho a

a Yonsei University (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 PICOLINE; 2 AMINOPYRIDINE DERIVATIVE; ALKENE; BENZOIC ACID; IMINE; KETONE; METHANOL; METHYLAMINE; PYRIDINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHELATION; DEHYDROGENATION; HYDROGEN BOND; HYDROLYSIS;

EID: 56349129242 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b814166e Document Type: Article

Times cited : (40)

References (57)

1
- 40549088216
- Y. J. Park J.-W. Park C.-H. Jun Acc. Chem. Res. 2008 41 222
- (2008) Acc. Chem. Res. , vol.41 , pp. 222
- Park, Y.J.¹ Park, J.-W.² Jun, C.-H.³

2
- 77954611953
- P. L. Fuchs, Wiley, New York
- Handbook of Reagents for Organic Synthesis, Reagents for Direct Functionalization of C-H Bonds, ed., P. L. Fuchs,, Wiley, New York, 2007
- (2007) Handbook of Reagents for Organic Synthesis, Reagents for Direct Functionalization of C-H Bonds, Ed.

3
- 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

4
- 34250655628
- I. V. Seregin V. Gevorgyan Chem. Soc. Rev. 2007 36 1173
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1173
- Seregin, I.V.¹ Gevorgyan, V.²

5
- 33645674829
- K. Godula D. Sames Science 2006 312 67
- (2006) Science , vol.312 , pp. 67
- Godula, K.¹ Sames, D.²

6
- 0242526099
- F. Kakiuchi N. Chatani Adv. Synth. Catal. 2003 345 1077
- (2003) Adv. Synth. Catal. , vol.345 , pp. 1077
- Kakiuchi, F.¹ Chatani, N.²

7
- 0036589261
- V. Ritleng C. Sirlin M. Pfeffer Chem. Rev. 2002 102 1731
- (2002) Chem. Rev. , vol.102 , pp. 1731
- Ritleng, V.¹ Sirlin, C.² Pfeffer, M.³

8
- 0036800380
- F. Kakiuchi S. Murai Acc. Chem. Res. 2002 35 826
- (2002) Acc. Chem. Res. , vol.35 , pp. 826
- Kakiuchi, F.¹ Murai, S.²

9
- 0037198618
- J. A. Labinger J. E. Bercaw Nature 2002 417 507
- (2002) Nature , vol.417 , pp. 507
- Labinger, J.A.¹ Bercaw, J.E.²

10
- 0033119285
- B. Rybtchinski D. Milstein Angew. Chem., Int. Ed. 1999 38 870
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 870
- Rybtchinski, B.¹ Milstein, D.²

11
- 0012233552
- A. E. Shilov G. B. Shul'pin Chem. Rev. 1997 97 2879
- (1997) Chem. Rev. , vol.97 , pp. 2879
- Shilov, A.E.¹ Shul'Pin, G.B.²

12
- 34547213920
- R. T. Stemmler C. Bolm Adv. Synth. Catal. 2007 349 1185
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1185
- Stemmler, R.T.¹ Bolm, C.²

13
- 34147095358
- K. Tanaka Y. Shibata T. Suda Y. Hagiwara M. Hirano Org. Lett. 2007 9 1215
- (2007) Org. Lett. , vol.9 , pp. 1215
- Tanaka, K.¹ Shibata, Y.² Suda, T.³ Hagiwara, Y.⁴ Hirano, M.⁵

14
- 34047192363
- M. Imai M. Tanaka S. Nagumo N. Kawahara H. Suemune J. Org. Chem. 2007 72 2543
- (2007) J. Org. Chem. , vol.72 , pp. 2543
- Imai, M.¹ Tanaka, M.² Nagumo, S.³ Kawahara, N.⁴ Suemune, H.⁵

15
- 33847291824
- A. H. Roy C. P. Lenges M. Brookhart J. Am. Chem. Soc. 2007 129 2082
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 2082
- Roy, A.H.¹ Lenges, C.P.² Brookhart, M.³

16
- 33847234334
- X. Y. Rueda S. Castillón J. Organomet. Chem. 2007 692 1628
- (2007) J. Organomet. Chem. , vol.692 , pp. 1628
- Rueda, X.Y.¹ Castillón, S.²

17
- 33745714355
- M. C. Willis H. E. Randell-Sly R. L. Woodward S. J. McNally G. S. Currie J. Org. Chem. 2006 71 5291
- (2006) J. Org. Chem. , vol.71 , pp. 5291
- Willis, M.C.¹ Randell-Sly, H.E.² Woodward, R.L.³ McNally, S.J.⁴ Currie, G.S.⁵

18
- 33845204295
- G. L. Moxham H. E. Randell-Sly S. K. Brayshaw R. L. Woodward A. S. Weller M. C. Willis Angew. Chem., Int. Ed. 2006 45 7618
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 7618
- Moxham, G.L.¹ Randell-Sly, H.E.² Brayshaw, S.K.³ Woodward, R.L.⁴ Weller, A.S.⁵ Willis, M.C.⁶

19
- 0346500648
- M. C. Willis S. J. McNally P. J. Beswick Angew. Chem., Int. Ed. 2004 43 340
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 340
- Willis, M.C.¹ McNally, S.J.² Beswick, P.J.³

20
- 33751553536
- T. Tsuda T. Kiyoi T. Saegusa J. Org. Chem. 1990 55 2554
- (1990) J. Org. Chem. , vol.55 , pp. 2554
- Tsuda, T.¹ Kiyoi, T.² Saegusa, T.³

21
- 34250618375
- C.-H. Jun E.-A. Jo J.-W. Park Eur. J. Org. Chem. 2007 1869
- (2007) Eur. J. Org. Chem. , pp. 1869
- Jun, C.-H.¹ Jo, E.-A.² Park, J.-W.³

22
- 0037124892
- C.-H. Jun H. Lee J.-B. Hong B.-I. Kwon Angew. Chem., Int. Ed. 2002 41 2146
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2146
- Jun, C.-H.¹ Lee, H.² Hong, J.-B.³ Kwon, B.-I.⁴

23
- 0034283369
- C.-H. Jun D.-Y. Lee H. Lee J.-B. Hong Angew. Chem., Int. Ed. 2000 39 3070
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3070
- Jun, C.-H.¹ Lee, D.-Y.² Lee, H.³ Hong, J.-B.⁴

24
- 0000685510
- C.-H. Jun H. Lee J.-B. Hong J. Org. Chem. 1997 62 1200
- (1997) J. Org. Chem. , vol.62 , pp. 1200
- Jun, C.-H.¹ Lee, H.² Hong, J.-B.³

25
- 33746630451
- D.-W. Kim S.-G. Lim C.-H. Jun Org. Lett. 2006 8 2937
- (2006) Org. Lett. , vol.8 , pp. 2937
- Kim, D.-W.¹ Lim, S.-G.² Jun, C.-H.³

26
- 0346456940
- D.-H. Chang D.-Y. Lee B.-S. Hong J.-H. Choi C.-H. Jun J. Am. Chem. Soc. 2004 126 424
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 424
- Chang, D.-H.¹ Lee, D.-Y.² Hong, B.-S.³ Choi, J.-H.⁴ Jun, C.-H.⁵

27
- 0037205035
- D.-Y. Lee C. W. Moon C.-H. Jun J. Org. Chem. 2002 67 3945
- (2002) J. Org. Chem. , vol.67 , pp. 3945
- Lee, D.-Y.¹ Moon, C.W.² Jun, C.-H.³

28
- 0031905843
- C.-H. Jun C.-W. Huh S.-J. Na Angew. Chem., Int. Ed. 1998 37 145
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 145
- Jun, C.-H.¹ Huh, C.-W.² Na, S.-J.³

29
- 0037119323
- D.-Y. Lee I.-J. Kim C.-H. Jun Angew. Chem., Int. Ed. 2002 41 3031
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3031
- Lee, D.-Y.¹ Kim, I.-J.² Jun, C.-H.³

30
- 0000831355
- C.-H. Jun H. Lee J.-B. Park D.-Y. Lee Org. Lett. 1999 1 2161
- (1999) Org. Lett. , vol.1 , pp. 2161
- Jun, C.-H.¹ Lee, H.² Park, J.-B.³ Lee, D.-Y.⁴

31
- 0006472135
- M. L. N. Rao M. Periasamy J. Organomet. Chem. 1998 553 91
- (1998) J. Organomet. Chem. , vol.553 , pp. 91
- Rao, M.L.N.¹ Periasamy, M.²

32
- 0004481708
- C. Narayana M. Periasamy Tetrahedron Lett. 1985 26 6361
- (1985) Tetrahedron Lett. , vol.26 , pp. 6361
- Narayana, C.¹ Periasamy, M.²

33
- 37049111527
- 2(CO)RhCl showed a comparable isolated yield (82%) of 5a under the identical reaction conditions to those in Table 1 In a separate experiment, the reaction of formaldehyde, in the form of paraformaldehyde, with 2-amino-4-picoline in the presence of benzoic acid did not give 7, but resulted in a stable aminal compound, which did not react with alkene under Rh(i) catalyst 2. For the stepwise reaction, see ESI
- V. N. Zudin G. N. Il'inich V. A. Likholobov Y. I. Yermakov J. Chem. Soc., Chem. Commun. 1984 545
- (1984) J. Chem. Soc., Chem. Commun. , pp. 545
- Zudin, V.N.¹ Il'Inich, G.N.² Likholobov, V.A.³ Yermakov, Y.I.⁴

34
- 17844398858
- A. D. Zotto W. Baratta M. Sandri G. Verardo P. Rigo Eur. J. Inorg. Chem. 2004 524
- (2004) Eur. J. Inorg. Chem. , pp. 524
- Zotto, A.D.¹ Baratta, W.² Sandri, M.³ Verardo, G.⁴ Rigo, P.⁵

35
- 2942590280
- T. Oku Y. Arita H. Tsuneki T. Ikariya J. Am. Chem. Soc. 2004 126 7368
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 7368
- Oku, T.¹ Arita, Y.² Tsuneki, H.³ Ikariya, T.⁴

36
- 0002155935
- K.-T. Huh Y. Tsuji M. Kobayashi F. Okuda Y. Watanabe Chem. Lett. 1988 449
- (1988) Chem. Lett. , pp. 449
- Huh, K.-T.¹ Tsuji, Y.² Kobayashi, M.³ Okuda, F.⁴ Watanabe, Y.⁵

37
- 33845469569
- Y. Watanabe Y. Tsuji H. Ige Y. Ohsugi T. Ohta J. Org. Chem. 1984 49 3359
- (1984) J. Org. Chem. , vol.49 , pp. 3359
- Watanabe, Y.¹ Tsuji, Y.² Ige, H.³ Ohsugi, Y.⁴ Ohta, T.⁵

38
- 43249121654
- R. Giri N. Maugel B. M. Foxman J.-Q. Yu Organometallics 2008 27 1667
- (2008) Organometallics , vol.27 , pp. 1667
- Giri, R.¹ Maugel, N.² Foxman, B.M.³ Yu, J.-Q.⁴

39
- 0000515670
- C.-H. Jun K.-Y. Chung J.-B. Hong Org. Lett. 2001 3 785
- (2001) Org. Lett. , vol.3 , pp. 785
- Jun, C.-H.¹ Chung, K.-Y.² Hong, J.-B.³

40
- 0033531615
- F. Liu A. S. Goldman Chem. Commun. 1999 655
- (1999) Chem. Commun. , pp. 655
- Liu, F.¹ Goldman, A.S.²

41
- 0001184450
- In the absence of benzoic acid (4), N-methylated compound 8 was isolated in only 7% yield. When the reaction of 8 with norbornene (1a) was carried out under the identical reaction conditions without 4, 5a was isolated in only 65% yield. Based on these results, benzoic acid can be considered as catalyst for N-methylation and/or hydrolysis of the resulting imine in Scheme 3
- N. Yoshimura I. Moritani T. Shimamura S.-I. Murahashi J. Am. Chem. Soc. 1973 95 3038
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 3038
- Yoshimura, N.¹ Moritani, I.² Shimamura, T.³ Murahashi, S.-I.⁴

42
- 33746302757
- M. Tobisu N. Chatani Angew. Chem., Int. Ed. 2006 45 1683
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1683
- Tobisu, M.¹ Chatani, N.²

43
- 33750509858
- J.-Q. Yu R. Giri X. Chen Org. Biomol. Chem. 2006 4 4041
- (2006) Org. Biomol. Chem. , vol.4 , pp. 4041
- Yu, J.-Q.¹ Giri, R.² Chen, X.³

44
- 19744365933
- D. Kalyani N. R. Deprez L. V. Desai M. S. Sanford J. Am. Chem. Soc. 2005 127 7330
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 7330
- Kalyani, D.¹ Deprez, N.R.² Desai, L.V.³ Sanford, M.S.⁴

45
- 24044442880
- D. Shabashov O. Daugulis Org. Lett. 2005 7 3657
- (2005) Org. Lett. , vol.7 , pp. 3657
- Shabashov, D.¹ Daugulis, O.²

46
- 5644288492
- F. Kakiuchi K. Tsuchiya M. Matsumoto E. Mizushima N. Chatani J. Am. Chem. Soc. 2004 126 12792
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 12792
- Kakiuchi, F.¹ Tsuchiya, K.² Matsumoto, M.³ Mizushima, E.⁴ Chatani, N.⁵

47
- 0034678111
- H. Chen S. Schlecht T. C. Semple J. F. Hartwig Science 2000 287 1995
- (2000) Science , vol.287 , pp. 1995
- Chen, H.¹ Schlecht, S.² Semple, T.C.³ Hartwig, J.F.⁴

48
- 34250769398
- K. R. Campos Chem. Soc. Rev. 2007 36 1069
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1069
- Campos, K.R.¹

49
- 34249778089
- S. B. Herzon J. F. Hartwig J. Am. Chem. Soc. 2007 129 6690
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6690
- Herzon, S.B.¹ Hartwig, J.F.²

50
- 27544488753
- S.-I. Murahashi N. Komiya H. Terai Angew. Chem., Int. Ed. 2005 44 6931
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6931
- Murahashi, S.-I.¹ Komiya, N.² Terai, H.³

51
- 3543057683
- L. V. Desai K. L. Hull M. S. Sanford J. Am. Chem. Soc. 2004 126 9542
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 9542
- Desai, L.V.¹ Hull, K.L.² Sanford, M.S.³

52
- 0035823825
- N. Chatani T. Asaumi S. Yorimitsu T. Ikeda F. Kakiuchi S. Murai J. Am. Chem. Soc. 2001 123 10935
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 10935
- Chatani, N.¹ Asaumi, T.² Yorimitsu, S.³ Ikeda, T.⁴ Kakiuchi, F.⁵ Murai, S.⁶

53
- 0034722947
- N. Chatani T. Asaumi T. Ikeda S. Yorimitsu Y. Ishii F. Kakiuchi S. Murai J. Am. Chem. Soc. 2000 122 12882
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 12882
- Chatani, N.¹ Asaumi, T.² Ikeda, T.³ Yorimitsu, S.⁴ Ishii, Y.⁵ Kakiuchi, F.⁶ Murai, S.⁷

54
- 0003111171
- C.-H. Jun D.-C. Hwang S.-J. Na Chem. Commun. 1998 1405
- (1998) Chem. Commun. , pp. 1405
- Jun, C.-H.¹ Hwang, D.-C.² Na, S.-J.³

55
- 0000626605
- 2O. See, for example:
- W. A. Nugent D. W. Ovenall S. J. Holmes Organometallics 1983 2 161
- (1983) Organometallics , vol.2 , pp. 161
- Nugent, W.A.¹ Ovenall, D.W.² Holmes, S.J.³

56
- 84962432234
- G. Kovács G. Schubert F. Joó I. Pápai Organometallics 2005 24 3059
- (2005) Organometallics , vol.24 , pp. 3059
- Kovács, G.¹ Schubert, G.² Joó, F.³ Pápai, I.⁴

57
- 8344272116
- B. J. Frost C. A. Mebi Organometallics 2004 23 5317
- (2004) Organometallics , vol.23 , pp. 5317
- Frost, B.J.¹ Mebi, C.A.²

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