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Chemistry - A European Journal

Volumn 18, Issue 46, 2012, Pages 14841-14844

Copper-catalyzed three-component borylstannylation of alkynes

(3) Takemoto, Yuki a Yoshida, Hiroto a Takaki, Ken a

a HIROSHIMA UNIVERSITY (Japan)

Author keywords

alkynes; boron; copper; tin; total synthesis

Indexed keywords

ALKOXIDES; ALKYNES; CARBON-BORON BONDS; CARBON-CARBON BOND; CARBON-CARBON TRIPLE BONDS; CATALYSE; STEREO-SELECTIVE; STEREOSELECTIVE MANNER; SUZUKI-MIYAURA COUPLING; SYNTHETIC UTILITY; TAMOXIFEN; THREE-COMPONENT; THREE-COMPONENT COUPLING REACTION; THREE-STEP SYNTHESIS; TOTAL SYNTHESIS;

ACETYLENE; BORON; CARBON; CHEMICAL REACTIONS; COPPER; STEREOSELECTIVITY; TIN;

COPPER COMPOUNDS;

ALKYNE; BORON DERIVATIVE; COPPER; ORGANOTIN COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKYNES; BORON COMPOUNDS; CATALYSIS; COPPER; MOLECULAR STRUCTURE; ORGANOTIN COMPOUNDS; STEREOISOMERISM;

EID: 84868706926 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201202435 Document Type: Article

Times cited : (76)

References (64)

1
- 0001034345
- I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435
- (1999) Chem. Rev. , vol.99 , pp. 3435
- Beletskaya, I.¹ Moberg, C.²

2
- 0034245862
- M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221
- (2000) Chem. Rev. , vol.100 , pp. 3221
- Suginome, M.¹ Ito, Y.²

3
- 33745712700
- I. Beletskaya, C. Moberg, Chem. Rev. 2006, 106, 2320.
- (2006) Chem. Rev. , vol.106 , pp. 2320
- Beletskaya, I.¹ Moberg, C.²

4
- 33845374625
- B. L. Chenard, C. M. Van Zyl, J. Org. Chem. 1986, 51, 3561
- (1986) J. Org. Chem. , vol.51 , pp. 3561
- Chenard, B.L.¹ Van Zyl, C.M.²

5
- 0001497199
- T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, U. Schneider, J. Org. Chem. 1987, 52, 4868
- (1987) J. Org. Chem. , vol.52 , pp. 4868
- Mitchell, T.N.¹ Wickenkamp, R.² Amamria, A.³ Dicke, R.⁴ Schneider, U.⁵

6
- 0000288660
- M. Murakami, H. Amii, N. Takizawa, Y. Ito, Organometallics 1993, 12, 4223
- (1993) Organometallics , vol.12 , pp. 4223
- Murakami, M.¹ Amii, H.² Takizawa, N.³ Ito, Y.⁴

7
- 3042793632
- M. Murakami, T. Matsuda, K. Itami, S. Ashida, M. Terayama, Synthesis 2004, 1522.
- (2004) Synthesis , pp. 1522
- Murakami, M.¹ Matsuda, T.² Itami, K.³ Ashida, S.⁴ Terayama, M.⁵

8
- 0002087649
- M. Suginome, H. Nakamura, Y. Ito, Chem. Commun. 1996, 2777
- (1996) Chem. Commun. , pp. 2777
- Suginome, M.¹ Nakamura, H.² Ito, Y.³

9
- 0001954878
- S.-y. Onozawa, Y. Hatanaka, M. Tanaka, Chem. Commun. 1997, 1229
- (1997) Chem. Commun. , pp. 1229
- O, S.-Y.¹ Hatanaka, Y.² Tanaka, M.³

10
- 0033575411
- M. Suginome, T. Matsuda, H. Nakamura, Y. Ito, Tetrahedron 1999, 55, 8787
- (1999) Tetrahedron , vol.55 , pp. 8787
- Suginome, M.¹ Matsuda, T.² Nakamura, H.³ Ito, Y.⁴

11
- 58349090006
- T. Ohmura, M. Suginome, Bull. Chem. Soc. Jpn. 2009, 82, 29.
- (2009) Bull. Chem. Soc. Jpn. , vol.82 , pp. 29
- Ohmura, T.¹ Suginome, M.²

12
- 0001594065
- S.-y. Onozawa, Y. Hatanaka, T. Sakakura, S. Shimada, M. Tanaka, Organometallics 1996, 15, 5450
- (1996) Organometallics , vol.15 , pp. 5450
- O, S.-Y.¹ Hatanaka, Y.² Sakakura, T.³ Shimada, S.⁴ Tanaka, M.⁵

13
- 0034229651
- L. Weber, H. B. Wartig, H. G. Stammler, A. Stammler, B. Neumann, Organometallics 2000, 19, 2891
- (2000) Organometallics , vol.19 , pp. 2891
- Weber, L.¹ Wartig, H.B.² Stammler, H.G.³ Stammler, A.⁴ Neumann, B.⁵

14
- 77953011564
- R. R. Singidi, T. V. Ra-janBabu, Org. Lett. 2010, 12, 2622.
- (2010) Org. Lett. , vol.12 , pp. 2622
- Singidi, R.R.¹ Ra-Janbabu, T.V.²

15
- 20544450502
- (Eds: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim.
- Metal-Catalyzed Cross-Coupling Reactions, (Eds:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004.
- (2004) Metal-Catalyzed Cross-Coupling Reactions

16
- 0028039416
- R. A. Magarian, L. B. Overacre, S. Singh, K. L. Meyer, Curr. Med. Chem. 1994, 1, 61
- (1994) Curr. Med. Chem. , vol.1 , pp. 61
- Magarian, R.A.¹ Overacre, L.B.² Singh, S.³ Meyer, K.L.⁴

17
- 0037468902
- V. C. Jordan, J. Med. Chem. 2003, 46, 1081.
- (2003) J. Med. Chem. , vol.46 , pp. 1081
- Jordan, V.C.¹

18
- 0020375149
- P. C. Ruenitz, J. R. Bagley, C. M. Mokler, J. Med. Chem. 1982, 25, 1056
- (1982) J. Med. Chem. , vol.25 , pp. 1056
- Ruenitz, P.C.¹ Bagley, J.R.² Mokler, C.M.³

19
- 0037102121
- A. Howell, J. F. R. Robertson, J. Quaresma Albano, A. Aschermannova, L. Mauriac, U. R. Kleeberg, I. Vergote, B. Erikstein, A. Webster, C. Morris, J. Clin. Oncol. 2002, 20, 3396.
- (2002) J. Clin. Oncol. , vol.20 , pp. 3396
- Howell, A.¹ Robertson, J.F.R.² Quaresma Albano, J.³ Aschermannova, A.⁴ Mauriac, L.⁵ Kleeberg, U.R.⁶ Vergote, I.⁷ Erikstein, B.⁸ Webster, A.⁹ Morris, C.¹⁰

20
- 0345257213
- J. Ellmén, P. Hakulinen, A. Partanen, D. F. Hayes, Breast Cancer Res. Treat. 2003, 82, 103
- (2003) Breast Cancer Res. Treat. , vol.82 , pp. 103
- Ellmén, J.¹ Hakulinen, P.² Partanen, A.³ Hayes, D.F.⁴

21
- 8744245366
- M. Kusama, K. Miyauchi, H. Aoyama, M. Sano, M. Kimura, S. Mitsuyama, K. Komaki, H. Doihara, Breast Cancer Res. Treat. 2004, 88, 1.
- (2004) Breast Cancer Res. Treat. , vol.88 , pp. 1
- Kusama, M.¹ Miyauchi, K.² Aoyama, H.³ Sano, M.⁴ Kimura, M.⁵ Mitsuyama, S.⁶ Komaki, K.⁷ Doihara, H.⁸

22
- 0006995161
- T. Hata, H. Kitagawa, H. Masai, T. Kurahashi, M. Shimizu, T. Hiyama, Angew. Chem. 2001, 113, 812
- (2001) Angew. Chem. , vol.113 , pp. 812
- Hata, T.¹ Kitagawa, H.² Masai, H.³ Kurahashi, T.⁴ Shimizu, M.⁵ Hiyama, T.⁶

23
- 0035804396
- Angew. Chem. Int. Ed. 2001, 40, 790
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 790

24
- 0037025959
- T. Kurahashi, T. Hata, H. Masai, H. Kitagawa, M. Shimizu, T. Hiyama, Tetrahedron 2002, 58, 6381.
- (2002) Tetrahedron , vol.58 , pp. 6381
- Kurahashi, T.¹ Hata, T.² Masai, H.³ Kitagawa, H.⁴ Shimizu, M.⁵ Hiyama, T.⁶

25
- 84865480585
- H. Yoshida, S. Kawashima, Y. Takemoto, K. Okada, J. Ohshita, K. Takaki, Angew. Chem. 2012, 124, 239
- (2012) Angew. Chem. , vol.124 , pp. 239
- Yoshida, H.¹ Kawashima, S.² Takemoto, Y.³ Okada, K.⁴ Ohshita, J.⁵ Takaki, K.⁶

26
- 84855264175
- Angew. Chem. Int. Ed. 2012, 51, 235.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 235

27
- 74549156927
- H. Ito, Y. Kosaka, K. Nonoyama, Y. Sasaki, M. Sawamura, Angew. Chem. 2008, 120, 7534
- (2008) Angew. Chem. , vol.120 , pp. 7534
- Ito, H.¹ Kosaka, Y.² Nonoyama, K.³ Sasaki, Y.⁴ Sawamura, M.⁵

28
- 54749136535
- Angew. Chem. Int. Ed. 2008, 47, 7424
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7424

29
- 73649139021
- C. Kleeberg, L. Dang, Z. Lin, T. B. Marder, Angew. Chem. 2009, 121, 5454
- (2009) Angew. Chem. , vol.121 , pp. 5454
- Kleeberg, C.¹ Dang, L.² Lin, Z.³ Marder, T.B.⁴

30
- 70349897198
- Angew. Chem. Int. Ed. 2009, 48, 5350
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5350

31
- 77954545005
- M. Tobisu, H. Fujihara, K. Koh, N. Chatani, J. Org. Chem. 2010, 75, 4841
- (2010) J. Org. Chem. , vol.75 , pp. 4841
- Tobisu, M.¹ Fujihara, H.² Koh, K.³ Chatani, N.⁴

32
- 77951694218
- H. Ito, T. Toyoda, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 5990
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 5990
- Ito, H.¹ Toyoda, T.² Sawamura, M.³

33
- 77955834388
- C. Zhong, S. Kunii, Y. Kosaka, M. Sawamura, H. Ito, J. Am. Chem. Soc. 2010, 132, 11440
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 11440
- Zhong, C.¹ Kunii, S.² Kosaka, Y.³ Sawamura, M.⁴ Ito, H.⁵

34
- 84863290857
- C.-T. Yang, Z.-Q. Zhang, H. Tajuddin, C.-C. Wu, J. Liang, J.-H. Liu, Y. Fu, M. Czyzewska, P. G. Steel, T. B. Marder, L. Liu, Angew. Chem. 2012, 124, 543
- (2012) Angew. Chem. , vol.124 , pp. 543
- Yang, C.-T.¹ Zhang, Z.-Q.² Tajuddin, H.³ Wu, C.-C.⁴ Liang, J.⁵ Liu, J.-H.⁶ Fu, Y.⁷ Czyzewska, M.⁸ Steel, P.G.⁹ Marder, T.B.¹⁰ Liu, L.¹¹

35
- 84855464257
- Angew. Chem. Int. Ed. 2012, 51, 528.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 528

36
- 56449084526
- J. Takaya, S. Tadami, K. Ukai, N. Iwasawa, Org. Lett. 2008, 10, 2697
- (2008) Org. Lett. , vol.10 , pp. 2697
- Takaya, J.¹ Tadami, S.² Ukai, K.³ Iwasawa, N.⁴

37
- 58149385034
- T. Ohishi, M. Nishiura, Z. Hou, Angew. Chem. 2008, 120, 5876
- (2008) Angew. Chem. , vol.120 , pp. 5876
- Ohishi, T.¹ Nishiura, M.² Hou, Z.³

38
- 53549095988
- Angew. Chem. Int. Ed. 2008, 47, 5792
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5792

39
- 84855434545
- C.-T. Yang, Z.-Q. Zhang, T.-C. Liu, L. Liu, Angew. Chem. 2011, 123, 3990
- (2011) Angew. Chem. , vol.123 , pp. 3990
- Yang, C.-T.¹ Zhang, Z.-Q.² Liu, T.-C.³ Liu, L.⁴

40
- 79954593181
- Angew. Chem. Int. Ed. 2011, 50, 3904
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 3904

41
- 79953019676
- T. Fujihara, T. Xu, K. Semba, J. Terao, Y. Tsuji, Angew. Chem. 2011, 123, 543
- (2011) Angew. Chem. , vol.123 , pp. 543
- Fujihara, T.¹ Xu, T.² Semba, K.³ Terao, J.⁴ Tsuji, Y.⁵

42
- 78650882267
- Angew. Chem. Int. Ed. 2011, 50, 523.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 523

43
- 0006272242
- K. Takahashi, T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47
- (2001) J. Organomet. Chem. , vol.625 , pp. 47
- Takahashi, K.¹ Ishiyama, T.² Miyaura, N.³

44
- 38849175563
- J.-E. Lee, J. Kwon, J. Yun, Chem. Commun. 2008, 733
- (2008) Chem. Commun. , pp. 733
- Lee, J.-E.¹ Kwon, J.² Yun, J.³

45
- 73249139284
- Y. Lee, H. Jang, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 18234
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 18234
- Lee, Y.¹ Jang, H.² Hoveyda, A.H.³

46
- 74549168596
- H.-R. Kim, I.-G. Jung, K. Yoo, K. Jang, E.-S. Lee, J. Yun, S.-U. Son, Chem. Commun. 2010, 46, 758
- (2010) Chem. Commun. , vol.46 , pp. 758
- Kim, H.-R.¹ Jung, I.-G.² Yoo, K.³ Jang, K.⁴ Lee, E.-S.⁵ Yun, J.⁶ Son, S.-U.⁷

47
- 79951866660
- H.-R. Kim, J. Yun, Chem. Commun. 2011, 47, 2943
- (2011) Chem. Commun. , vol.47 , pp. 2943
- Kim, H.-R.¹ Yun, J.²

48
- 84855417172
- Y. Sasaki, Y. Horita, C. Zhong, M. Sawamura, H. Ito, Angew. Chem. 2011, 123, 2830
- (2011) Angew. Chem. , vol.123 , pp. 2830
- Sasaki, Y.¹ Horita, Y.² Zhong, C.³ Sawamura, M.⁴ Ito, H.⁵

49
- 79952520006
- for the Cu-catalyzed synthesis of allenylboranes, see
- Angew. Chem. Int. Ed. 2011, 50, 2778; for the Cu-catalyzed synthesis of allenylboranes, see
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2778

50
- 56749169368
- for the Cu-catalyzed diborylation of alkynes, see ref. [10].
- H. Ito, Y. Sasaki, M. Sawamura, J. Am. Chem. Soc. 2008, 130, 15774; for the Cu-catalyzed diborylation of alkynes, see ref. [10].
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 15774
- Ito, H.¹ Sasaki, Y.² Sawamura, M.³

51
- 79957681266
- H. Jang, A. R. Zhugalin, Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 7859
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7859
- Jang, H.¹ Zhugalin, A.R.² Lee, Y.³ Hoveyda, A.H.⁴

52
- 84859319096
- see also ref. [13].
- K. Semba, T. Fujihara, J. Terao, Y. Tsuji, Chem. Eur. J. 2012, 18, 4179; see also ref. [13].
- (2012) Chem. Eur. J. , vol.18 , pp. 4179
- Semba, K.¹ Fujihara, T.² Terao, J.³ Tsuji, Y.⁴

53
- 41749083047
- For a computational study, see.
- For a computational study, see:, L. Dang, H. Zhao, Z. Lin, T. B. Marder, Organometallics 2008, 27, 1178.
- (2008) Organometallics , vol.27 , pp. 1178
- Dang, L.¹ Zhao, H.² Lin, Z.³ Marder, T.B.⁴

54
- 77954556988
- A. M. Whittaker, R. P. Rucker, G. Lalic, Org. Lett. 2010, 12, 3216
- (2010) Org. Lett. , vol.12 , pp. 3216
- Whittaker, A.M.¹ Rucker, R.P.² Lalic, G.³

55
- 77956317762
- see also refs. [12a-c].
- R. Shintani, K. Takatsu, T. Hayashi, Chem. Commun. 2010, 46, 6822; see also refs. [12a-c].
- (2010) Chem. Commun. , vol.46 , pp. 6822
- Shintani, R.¹ Takatsu, K.² Hayashi, T.³

56
- 77949410450
- K.-S. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 2898
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2898
- Lee, K.-S.¹ Hoveyda, A.H.²

57
- 79955368007
- D. J. Vyas, R. Fröhlich, M. Oestreich, Org. Lett. 2011, 13, 2094
- (2011) Org. Lett. , vol.13 , pp. 2094
- Vyas, D.J.¹ Fröhlich, R.² Oestreich, M.³

58
- 79551704043
- P. Wang, X.-L. Yeo, T.-P. Loh, J. Am. Chem. Soc. 2011, 133, 1254.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 1254
- Wang, P.¹ Yeo, X.-L.² Loh, T.-P.³

59
- 0345293203
- K. Itami, T. Kamei, J.-i. Yoshida, J. Am. Chem. Soc. 2003, 125, 14670
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14670
- Itami, K.¹ Kamei, T.² Y, J.-I.³

60
- 24744458162
- M. Shimizu, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc. 2005, 127, 12506
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 12506
- Shimizu, M.¹ Nakamaki, C.² Shimono, K.³ Schelper, M.⁴ Kurahashi, T.⁵ Hiyama, T.⁶

61
- 35548966067
- Y. Nishihara, M. Miyasaka, M. Okamoto, H. Takahashi, E. Inoue, K. Tanemura, K. Takagi, J. Am. Chem. Soc. 2007, 129, 12634
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12634
- Nishihara, Y.¹ Miyasaka, M.² Okamoto, M.³ Takahashi, H.⁴ Inoue, E.⁵ Tanemura, K.⁶ Takagi, K.⁷

62
- 72449130907
- N. Ishida, Y. Shimamoto, M. Murakami, Org. Lett. 2009, 11, 5434
- (2009) Org. Lett. , vol.11 , pp. 5434
- Ishida, N.¹ Shimamoto, Y.² Murakami, M.³

63
- 84865799519
- Z. He, S. Kirchberg, R. Fröhlich, A. Studer, Angew. Chem. 2012, 124, 3759
- (2012) Angew. Chem. , vol.124 , pp. 3759
- He, Z.¹ Kirchberg, S.² Fröhlich, R.³ Studer, A.⁴

64
- 84859524880
- Angew. Chem. Int. Ed. 2012, 51, 3699.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 3699

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