Highly efficient catalytic synthesis of substituted allenes using indium

Angewandte Chemie - International Edition

Volumn 41, Issue 20, 2002, Pages 3901-3903

  Lee, Kooyeon ^a   Seomoon, Dong ^a   Lee, Phil Ho ^a  

^a Kangwon National University   (South Korea)

Author keywords

Allenes; Cross coupling; Indium; Palladium

Indexed keywords

BROMINE COMPOUNDS; CHEMICAL REACTIONS; INDIUM COMPOUNDS; PALLADIUM;

CHEMOSELECTIVITY;

CATALYSIS;

ALLENE DERIVATIVE; INDIUM; PALLADIUM;

ARTICLE; CATALYSIS; PRODUCTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037131448     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021018)41:20<3901::AID-ANIE3901>3.0.CO;2-S     Document Type: Article

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54. For some previously reported examples of indium-mediated cross-coupling reactions, see: a) R. Nomura, S.-I. Miyazaki, H. Matsuda, J. Am. Chem. Soc. 1992, 114, 2738; b) I. Perez, J.P. Sestelo, L.A. Sarandeses, Org. Lett. 1999, 1, 1267; c) D. Gelman, H. Schumann, J. Blum, Tetrahedron Lett. 2000, 41, 7555; d) I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155; e) T. Hirashita, H. Yamamura, M. Kawai, S. Araki, Chem. Commun. 2001, 387; f) K. Takami, H. Yorimitsu, H. Shnokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 1997; g) P. H. Lee, S.-Y. Sung, K. Lee, Org. Lett. 2001, 3, 3201.
55. For some previously reported examples of indium-mediated cross-coupling reactions, see: a) R. Nomura, S.-I. Miyazaki, H. Matsuda, J. Am. Chem. Soc. 1992, 114, 2738; b) I. Perez, J.P. Sestelo, L.A. Sarandeses, Org. Lett. 1999, 1, 1267; c) D. Gelman, H. Schumann, J. Blum, Tetrahedron Lett. 2000, 41, 7555; d) I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155; e) T. Hirashita, H. Yamamura, M. Kawai, S. Araki, Chem. Commun. 2001, 387; f) K. Takami, H. Yorimitsu, H. Shnokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 1997; g) P. H. Lee, S.-Y. Sung, K. Lee, Org. Lett. 2001, 3, 3201.
56. For some previously reported examples of indium-mediated cross-coupling reactions, see: a) R. Nomura, S.-I. Miyazaki, H. Matsuda, J. Am. Chem. Soc. 1992, 114, 2738; b) I. Perez, J.P. Sestelo, L.A. Sarandeses, Org. Lett. 1999, 1, 1267; c) D. Gelman, H. Schumann, J. Blum, Tetrahedron Lett. 2000, 41, 7555; d) I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155; e) T. Hirashita, H. Yamamura, M. Kawai, S. Araki, Chem. Commun. 2001, 387; f) K. Takami, H. Yorimitsu, H. Shnokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 1997; g) P. H. Lee, S.-Y. Sung, K. Lee, Org. Lett. 2001, 3, 3201.
57. For some previously reported examples of indium-mediated cross-coupling reactions, see: a) R. Nomura, S.-I. Miyazaki, H. Matsuda, J. Am. Chem. Soc. 1992, 114, 2738; b) I. Perez, J.P. Sestelo, L.A. Sarandeses, Org. Lett. 1999, 1, 1267; c) D. Gelman, H. Schumann, J. Blum, Tetrahedron Lett. 2000, 41, 7555; d) I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155; e) T. Hirashita, H. Yamamura, M. Kawai, S. Araki, Chem. Commun. 2001, 387; f) K. Takami, H. Yorimitsu, H. Shnokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 1997; g) P. H. Lee, S.-Y. Sung, K. Lee, Org. Lett. 2001, 3, 3201.
58. For some previously reported examples of indium-mediated cross-coupling reactions, see: a) R. Nomura, S.-I. Miyazaki, H. Matsuda, J. Am. Chem. Soc. 1992, 114, 2738; b) I. Perez, J.P. Sestelo, L.A. Sarandeses, Org. Lett. 1999, 1, 1267; c) D. Gelman, H. Schumann, J. Blum, Tetrahedron Lett. 2000, 41, 7555; d) I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155; e) T. Hirashita, H. Yamamura, M. Kawai, S. Araki, Chem. Commun. 2001, 387; f) K. Takami, H. Yorimitsu, H. Shnokubo, S. Matsubara, K. Oshima, Org. Lett. 2001, 3, 1997; g) P. H. Lee, S.-Y. Sung, K. Lee, Org. Lett. 2001, 3, 3201.
59. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.
60. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.
61. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.
62. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.
63. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.
64. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.
65. 7]DMF, 25°C) spectrum of the allenylindium reagent shows signals at σ = 210.15, 71.80, 61.44. a) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; b) M. B. Isaac, T.-K. Chan, Chem. Commun. 1995, 1003; c) X.-H. Yi, C.-J. Li, Chem. Commun. 1998, 449; d) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; e) X.-H. Yi, Y. Meng, X.-G. Hua, C.-J. Li, J. Org. Chem. 1998, 63, 7472; f) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214; g) B. Alcaide, P. Almendros, C. Aragoncillo, Org. Lett. 2000, 2, 1411.