SCOPUS 정보 검색 플랫폼

Volumn 89, Issue 5, 2006, Pages 936-946

Convenient synthesis of 1H-indol-1-yl boronates via palladium(0)-catalyzed borylation of bromo-1H-indoles with 'pinacolborane'

(2) Stadlwieser, Josef F a Dambaur, Markus E a

a ALTANA PHARMA AG (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; PALLADIUM; STRUCTURE (COMPOSITION); SUBSTRATES; SYNTHESIS (CHEMICAL);

BROMOINDOLE; FUNCTIONAL GROUPS; LIGAND; PINACOLBORANE;

BORON COMPOUNDS;

1 (2 METHOXYETHYL) 4 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOLE; 1 [2 (4 METHYLPIPERAZIN 1 YL)ETHYL] 5 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOLE; 1 METHYL 4 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOLE; 1 METHYL 5 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOLE; 4 {[5 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOL 1 YL]METHYL}PIPERIDINE 1 CARBALDEHYDE; 5 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2YL) 1 [TRIS(1 METHYLETHYL)SILYL] 1H INDOLE; BORANE DERIVATIVE; INDOLE DERIVATIVE; METHYL [4 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOL 1 YL]ACETATE; N,N DIMETHYL 2 [5 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H INDOL 1 YL]ETHANAMINE; PALLADIUM; PINACOLBORANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33744959541 PISSN: 0018019X EISSN: None Source Type: Journal
DOI: 10.1002/hlca.200690097 Document Type: Article

Times cited : (15)

References (40)

1
- 84889494843
- Ed. D. G. Hall, Wiley-VCH, Weinheim
- 'Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine', Ed. D. G. Hall, Wiley-VCH, Weinheim, 2005.
- (2005) Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine

2
- 0037244546
- E. Tyrrell, P. Brookes, Synthesis 2004, 469.
- (2004) Synthesis , pp. 469
- Tyrrell, E.¹ Brookes, P.²

3
- 0003995267
- Eds. E. Negishi, A. de Meijere, Wiley-Interscience, New York
- 'Handbook of Organopalladium Chemistry for Organic Synthesis', Eds. E. Negishi, A. de Meijere, Wiley-Interscience, New York, 2002.
- (2002) 'Handbook of Organopalladium Chemistry for Organic Synthesis'

4
- 0003397781
- Eds. F. Diederich, P. J. Stang, Wiley-VCH, Weinheim
- 'Metal-Catalyzed Cross-Coupling Reactions', Eds. F. Diederich, P. J. Stang, Wiley-VCH, Weinheim, 1998.
- (1998) 'Metal-Catalyzed Cross-Coupling Reactions'

5
- 3242670935
- X. Cai, V. Snieckus, Org. Lett. 2004, 6, 2293;
- (2004) Org. Lett. , vol.6 , pp. 2293
- Cai, X.¹ Snieckus, V.²

6
- 0037347760
- A. Nishida, N. Miyashita, M. Fuwa, M. Nakagawa, Heterocycles 2003, 59, 473;
- (2003) Heterocycles , vol.59 , pp. 473
- Nishida, A.¹ Miyashita, N.² Fuwa, M.³ Nakagawa, M.⁴

7
- 33744951961
- C. G. Yang, G. Lui, B. Jiang, J. Org. Chem. 2002, 53, 9392;
- (2002) J. Org. Chem. , vol.53 , pp. 9392
- Yang, C.G.¹ Lui, G.² Jiang, B.³

8
- 0037131147
- E. Vazquez, I. W. Davies, J. F. Payack, J. Org. Chem. 2002, 67, 7551;
- (2002) J. Org. Chem. , vol.67 , pp. 7551
- Vazquez, E.¹ Davies, I.W.² Payack, J.F.³

9
- 0033582758
- K.-H. Doll, J. Org. Chem. 1999, 64, 1372;
- (1999) J. Org. Chem. , vol.64 , pp. 1372
- Doll, K.-H.¹

10
- 0000271948
- C. N. Johnson, G. Stemp, N. Anand, S. C. Stephen, T. Gallagher, Synlett 1998, 1025;
- (1998) Synlett , pp. 1025
- Johnson, C.N.¹ Stemp, G.² Anand, N.³ Stephen, S.C.⁴ Gallagher, T.⁵

11
- 0001762703
- R. S. Hoerner, D. Askin, R. P. Volante, P. J. Reider, Tetrahedron Lett. 1998, 39, 3455;
- (1998) Tetrahedron Lett. , vol.39 , pp. 3455
- Hoerner, R.S.¹ Askin, D.² Volante, R.P.³ Reider, P.J.⁴

12
- 0029853205
- I. Kawasaki, M. Yamashita, S. Ohta, Chem. Pharm. Bull. 1996, 44, 1831.
- (1996) Chem. Pharm. Bull. , vol.44 , pp. 1831
- Kawasaki, I.¹ Yamashita, M.² Ohta, S.³

13
- 0037025734
- J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama, N. Miyaura, Tetrahedron Lett. 2002, 43, 5649.
- (2002) Tetrahedron Lett. , vol.43 , pp. 5649
- Takagi, J.¹ Sato, K.² Hartwig, J.F.³ Ishiyama, T.⁴ Miyaura, N.⁵

14
- 12344285902
- T. Tagata, M. Nishida, Adv. Synth. Catal. 2004, 346, 1655.
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1655
- Tagata, T.¹ Nishida, M.²

15
- 0348161559
- K. Mertins, A. Zapf, M. Beller, J. Mol. Catal., A 2004, 207, 21.
- (2004) J. Mol. Catal., A , vol.207 , pp. 21
- Mertins, K.¹ Zapf, A.² Beller, M.³

16
- 0037119304
- T. Ishiyama, J. Takagi, J. F. Hartwig, N. Miyaura, Angew. Chem., Int. Ed. 2002, 41, 3056.
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3056
- Ishiyama, T.¹ Takagi, J.² Hartwig, J.F.³ Miyaura, N.⁴

17
- 0344874124
- T. Ishiyama, Y. Nobuta, J. F. Hartwig, N. Miyaura, Chem. Commun. 2003, 2924.
- (2003) Chem. Commun. , pp. 2924
- Ishiyama, T.¹ Nobuta, Y.² Hartwig, J.F.³ Miyaura, N.⁴

18
- 3142514770
- T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508.
- (1995) J. Org. Chem. , vol.60 , pp. 7508
- Ishiyama, T.¹ Murata, M.² Miyaura, N.³

19
- 1542719075
- T. Fryatt, H. I. Pettersson, W. T. Gardipee, K. C. Bray, S. J. Green, A. M. Z. Slawin, H. D. Beall, C. J. Moody, Bioorg. Med. Chem. 2004, 12, 1667.
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 1667
- Fryatt, T.¹ Pettersson, H.I.² Gardipee, W.T.³ Bray, K.C.⁴ Green, S.J.⁵ Slawin, A.M.Z.⁶ Beall, H.D.⁷ Moody, C.J.⁸

20
- 5644290625
- K. C. Nicolaou, J. Hao, M. V. Reddy, P. B. Rao, G. Rassias, S. A. Snyder, X. Huang, D. Y.-K. Chen, W. E. Brenzovich, N. Guiseppone, P. Giannakakou, A. O'Brate, J. Am. Chem. Soc. 2004, 126, 12897.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 12897
- Nicolaou, K.C.¹ Hao, J.² Reddy, M.V.³ Rao, P.B.⁴ Rassias, G.⁵ Snyder, S.A.⁶ Huang, X.⁷ Chen, D.Y.-K.⁸ Brenzovich, W.E.⁹ Guiseppone, N.¹⁰ Giannakakou, P.¹¹ O'Brate, A.¹²

21
- 0037541199
- K. C. Nicolaou, P. B. Rao, J. Hao, M. V. Reddy, G. Rassias, X. Huang, D. Y.-K. Chen, S. A. Snyder, Angew. Chem., Int. Ed. 2003, 42, 1753.
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1753
- Nicolaou, K.C.¹ Rao, P.B.² Hao, J.³ Reddy, M.V.⁴ Rassias, G.⁵ Huang, X.⁶ Chen, D.Y.-K.⁷ Snyder, S.A.⁸

22
- 0038729563
- P. Appukkuttan, E. Van der Eycken, W. Dehaen, Synlett 2003, 1204.
- (2003) Synlett , pp. 1204
- Appukkuttan, P.¹ Van Der Eycken, E.² Dehaen, W.³

23
- 0035802895
- T. Ishiyama, K. Ishida, N. Miyaura, Tetrahedron 2001, 57, 9813.
- (2001) Tetrahedron , vol.57 , pp. 9813
- Ishiyama, T.¹ Ishida, K.² Miyaura, N.³

24
- 4644242942
- M. Prieto, E. Zurita, E. Rosa, L. Munoz, P. Lloyd-Williams, E. Giralt, J. Org. Chem. 2004, 69, 6812.
- (2004) J. Org. Chem. , vol.69 , pp. 6812
- Prieto, M.¹ Zurita, E.² Rosa, E.³ Munoz, L.⁴ Lloyd-Williams, P.⁵ Giralt, E.⁶

25
- 0025246361
- R. M. Soll, J. A. Parks, T. J. Rimele, R. J. Haeslip, A. Wojdan, G. Oshiro, D. Grimes, A. Asselin, Eur. J. Med. Chem. 1990, 25, 191.
- (1990) Eur. J. Med. Chem. , vol.25 , pp. 191
- Soll, R.M.¹ Parks, J.A.² Rimele, T.J.³ Haeslip, R.J.⁴ Wojdan, A.⁵ Oshiro, G.⁶ Grimes, D.⁷ Asselin, A.⁸

26
- 0024206919
- P. J. Beswick, C. S. Greenwood, T. J. Mowlem, G. Nechwatal, D. A. Widdowson, Tetrahedron 1988, 44, 7325.
- (1988) Tetrahedron , vol.44 , pp. 7325
- Beswick, P.J.¹ Greenwood, C.S.² Mowlem, T.J.³ Nechwatal, G.⁴ Widdowson, D.A.⁵

27
- 20444468561
- H. Ohno, K. Miyamura, T. Mizutani, Y. Kadoh, Y. Takeoka, H. Hamaguchi, T. Tanaka, Chem.-Eur. J. 2005, 11, 3728.
- (2005) Chem.-Eur. J. , vol.11 , pp. 3728
- Ohno, H.¹ Miyamura, K.² Mizutani, T.³ Kadoh, Y.⁴ Takeoka, Y.⁵ Hamaguchi, H.⁶ Tanaka, T.⁷

28
- 25444435181
- J. Baudoux, A. J. Blake, N. S. Simkins, Org. Lett. 2005, 7, 4087.
- (2005) Org. Lett. , vol.7 , pp. 4087
- Baudoux, J.¹ Blake, A.J.² Simkins, N.S.³

29
- 10744230198
- M. Isaac, M. Slassi, T. Xin, J. Arora, A. O'Brian, L. Edwards, N. MacLean, J. Wilson, L. Demschyshin, P. Labrie, A. Naismith, S. Maddaford, D. Papac, S. Harrison, H. Wang, S. Draper, A. Tehim, Bioorg. Med. Chem. Lett. 2003, 13, 4409.
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 4409
- Isaac, M.¹ Slassi, M.² Xin, T.³ Arora, J.⁴ O'Brian, A.⁵ Edwards, L.⁶ MacLean, N.⁷ Wilson, J.⁸ Demschyshin, L.⁹ Labrie, P.¹⁰ Naismith, A.¹¹ Maddaford, S.¹² Papac, D.¹³ Harrison, S.¹⁴ Wang, H.¹⁵ Draper, S.¹⁶ Tehim, A.¹⁷

30
- 0032544472
- K. M. Jos Brands, U.-H. Dolling, R. B. Jobson, G. Marchesini, R. A. Reamer, J. M. Williams, J. Org. Chem. 1998, 63, 6721.
- (1998) J. Org. Chem. , vol.63 , pp. 6721
- Jos Brands, K.M.¹ Dolling, U.-H.² Jobson, R.B.³ Marchesini, G.⁴ Reamer, R.A.⁵ Williams, J.M.⁶

31
- 0033958547
- M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164.
- (2000) J. Org. Chem. , vol.65 , pp. 164
- Murata, M.¹ Oyama, T.² Watanabe, S.³ Masuda, Y.⁴

32
- 0001766644
- M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem. 1997, 62, 6458.
- (1997) J. Org. Chem. , vol.62 , pp. 6458
- Murata, M.¹ Watanabe, S.² Masuda, Y.³

33
- 0000659668
- A. Fürstner, G. Seidel, Org. Lett. 2002, 4, 541.
- (2002) Org. Lett. , vol.4 , pp. 541
- Fürstner, A.¹ Seidel, G.²

34
- 16844367937
- T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685;
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4685
- Barder, T.E.¹ Walker, S.D.² Martinelli, J.R.³ Buchwald, S.L.⁴

35
- 5644254180
- J. E. Mine, S. L. Buchwald, J. Am. Chem. Soc. 2004, 126, 13028;
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 13028
- Mine, J.E.¹ Buchwald, S.L.²

36
- 0141843609
- H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818;
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11818
- Nguyen, H.N.¹ Huang, X.² Buchwald, S.L.³

37
- 0032747809
- J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550;
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9550
- Wolfe, J.P.¹ Singer, R.A.² Yang, B.H.³ Buchwald, S.L.⁴

38
- 0032560932
- D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1988, 120, 9722.
- (1988) J. Am. Chem. Soc. , vol.120 , pp. 9722
- Old, D.W.¹ Wolfe, J.P.² Buchwald, S.L.³

39
- 0345686421
- C. Christophersen, M. Bergtrup, S. Ebdrup, H. Petersen, P. Vedsø, J. Org. Chem. 2003, 68, 9513.
- (2003) J. Org. Chem. , vol.68 , pp. 9513
- Christophersen, C.¹ Bergtrup, M.² Ebdrup, S.³ Petersen, H.⁴ Vedsø, P.⁵

40
- 0034731579
- O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2000, 65, 9268.
- (2000) J. Org. Chem. , vol.65 , pp. 9268
- Baudoin, O.¹ Guénard, D.² Guéritte, F.³

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