Palladium(0)-catalyzed tandem cyclization of allenenes

Angewandte Chemie - International Edition

Volumn 42, Issue 23, 2003, Pages 2647-2650

  Ohno, Hiroaki ^a   Miyamura, Kumiko ^a   Takeoka, Yusuke ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Allenes; Cyclization; Domino reactions; Heterocycles; Palladium

Indexed keywords

CATALYSIS; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS;

TANDEM CYCLIZATION;

OLEFINS;

ALKENE; ALLENE DERIVATIVE; HETEROCYCLIC COMPOUND; IODINE DERIVATIVE; PALLADIUM; POTASSIUM CARBONATE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038451472     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351011     Document Type: Article

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52. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
53. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
54. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
55. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
56. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
57. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
58. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
59. For other cyclizations of allenenes, allenynes, or bisallenes, see: a) H. Urabe, T. Takeda, D. Hideura, F. Sato, J. Am. Chem. Soc. 1997, 119, 11295-11305; b) K. M. Brummond, J. Lu, J. Am. Chem. Soc. 1999, 121, 5087-5088; c) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349; d) C. H. Oh, S. H. Jung, C. Y. Rhim, Tetrahedron Lett. 2001, 42, 8669 -8671; e) S.-K. Kang, Y.-H. Ha, D.-H. Kim, Y. Lim, J. Jung, Chem. Commun. 2001, 1306-1307; f) Q. Shen, G. B. Hammond, J. Am. Chem. Soc. 2002, 124, 6534-6535; g) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758; h) S.-K. Kang, B.-S. Ko, D.-M. Lee, Tetrahedron Lett. 2002, 43, 6693-6696; i) K. M. Brummond, H. Chen, P. Sill, L. You, J. Am. Chem. Soc. 2002, 124, 15186-15187.
60. A palladium(II)-catalyzed domino cyclization of allenynes in the presence of LiBr under oxygen at atmospheric pressure was recently reported: B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Eur. J. 2002, 8, 1719-1729.
61. a) H. Ohno, A. Toda, S. Oishi, T. Tanaka, Y. Takemoto, N. Fujii, T. Ibuka, Tetrahedron Lett. 2000, 41, 5131-5134;
62. b) H. Ohno, K. Miyamura, T. Tanaka, S. Oishi, A. Toda, Y. Takemoto, N. Fujii, T. Ibuka, J. Org. Chem. 2002, 67, 1359-1367.
63. Confirmation of the stereochemistry of the cyclized products was based on NOE analysis (see the Supporting Information).
64. The reaction of the unsubstituted allenene (R = H) led to a complex mixture of unidentified products.
65. R. F. Heck, Acc. Chem. Res. 1979, 12, 146-151.
66. 2 mechanism can occur in limited cases. See, for example: a) J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956-5957; b) I. Schwarz, M. Braun, Chem. Eur. J. 1999, 5, 2300-2305, and references therein.
67. 2 mechanism can occur in limited cases. See, for example: a) J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956-5957; b) I. Schwarz, M. Braun, Chem. Eur. J. 1999, 5, 2300-2305, and references therein.