Synthesis of indoles upon sequential reaction of 3-alkynylpyrrole-2- carboxaldehydes with iodonium ions and alkenes. Preparation of related benzofuran and benzothiophene derivatives

Advanced Synthesis and Catalysis

Volumn 347, Issue 4, 2005, Pages 526-530

  Barluenga, José ^a   Vázquez Villa, Henar ^a   Ballesteros, Alfredo ^a   González, José M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkenes; Enamines; Indoles; Iodine; Pyrroles

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; ENAMINE; ETHER DERIVATIVE; INDOLE DERIVATIVE; IODINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COLUMN CHROMATOGRAPHY; CYCLIZATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 17144386613     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404293     Document Type: Article

References (57)

1. For recent overviews on indole synthesis, see, for in7 stance: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2848-2866; c) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075; d) J. J. Li, G. W. Gribble, in: Palladium in Heterocyclic Synthesis, Pergamon, Oxford 2000, pp. 73-181; e) S. Bräse, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437.
2. For recent overviews on indole synthesis, see, for in7 stance: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2848-2866; c) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075; d) J. J. Li, G. W. Gribble, in: Palladium in Heterocyclic Synthesis, Pergamon, Oxford 2000, pp. 73-181; e) S. Bräse, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437.
3. For recent overviews on indole synthesis, see, for in7 stance: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2848-2866; c) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075; d) J. J. Li, G. W. Gribble, in: Palladium in Heterocyclic Synthesis, Pergamon, Oxford 2000, pp. 73-181; e) S. Bräse, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437.
4. For recent overviews on indole synthesis, see, for in7 stance: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2848-2866; c) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075; d) J. J. Li, G. W. Gribble, in: Palladium in Heterocyclic Synthesis, Pergamon, Oxford 2000, pp. 73-181; e) S. Bräse, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437.
5. For recent overviews on indole synthesis, see, for in7 stance: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2848-2866; c) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075; d) J. J. Li, G. W. Gribble, in: Palladium in Heterocyclic Synthesis, Pergamon, Oxford 2000, pp. 73-181; e) S. Bräse, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437.
6. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
7. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
8. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
9. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
10. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
11. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
12. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
13. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
14. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
15. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
16. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
17. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
18. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
19. For recent examples, see: a) J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168-15169; b) C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054-4055; c) J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508-2511; Angew. Chem. Int. Ed. 2003, 42, 2406-2409; d) H. Siebeneicher, I. Bytschkov, S. Doyle, Angew. Chem. 2003, 115, 3151-3153; Angew. Chem. Int. Ed. 2003, 42, 3042-3044; e) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel Angew. Chem. 2003, 115, 4392-4396; Angew. Chem. Int. Ed. 2003, 42, 4257-4260; f) K. Campos, J. C. S. Woo, S. Lee, R. D. Tillyer, Org. Lett. 2004, 6, 79-82; g) M. Amjad, D.W. Knight, Tetrahedron Lett. 2004, 45, 539-541; h) D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037-1040; i) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618; j) M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 776, 4626-4629; Angew. Chem. Int. Ed. 2004, 43, 4526-4528.
20. For recent contributions, see: a) M. Beller, C. Breindl, T. H. Riermeier, A. Tillack, J. Org. Chem. 2001, 66, 1403-1412; b) J. Siu, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2004, 2, 160-167; for a regioselective modification of indole to obtain derivatives of the benzene moiety, see: c) C. G. Hartung, A. Fecher, B. Chapell, V. Snieckus, Org. Lett. 2003, 5, 1899-1902.
21. For recent contributions, see: a) M. Beller, C. Breindl, T. H. Riermeier, A. Tillack, J. Org. Chem. 2001, 66, 1403-1412; b) J. Siu, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2004, 2, 160-167; for a regioselective modification of indole to obtain derivatives of the benzene moiety, see: c) C. G. Hartung, A. Fecher, B. Chapell, V. Snieckus, Org. Lett. 2003, 5, 1899-1902.
22. For recent contributions, see: a) M. Beller, C. Breindl, T. H. Riermeier, A. Tillack, J. Org. Chem. 2001, 66, 1403-1412; b) J. Siu, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2004, 2, 160-167; for a regioselective modification of indole to obtain derivatives of the benzene moiety, see: c) C. G. Hartung, A. Fecher, B. Chapell, V. Snieckus, Org. Lett. 2003, 5, 1899-1902.
23. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
24. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
25. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
26. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
27. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
28. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
29. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
30. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
31. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
32. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
33. For early work, see, for instance: a) Y. Ito, K. Kobayashi, T. Saegusa, J. Am. Chem. Soc. 1977, 99, 3532-3534; b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31-32; c) J.-B. Baudin, S. A. Julia, Tetrahedron Lett. 1986, 27, 837-840; d) G. Bartoli, M. Bosco, R. Dalpozzo, G. Palmieri, E. Mercantoni, J. Chem. Soc. Perkin Trans. 1, 1991, 2757-2761; e) G. M. Carrera, Jr., G. S. Sheppard, Synlett 1994, 93-94; f) L.-M. Yang, C.-F Chen, K.-H. Lee, Bioorg. Med. Chem. Lett. 1995, 5, 465-468; g) H. D. H. Showalter, L. Sun, A. D. Sercel, R. T. Winters, W. A. Denny, B. D. Palmer, J. Org. Chem. 1996, 61, 1155-1158; h) Y. Aoyagi, T. Mizusaki, A. Ohta, Tetrahedron Lett. 1996, 37, 9203-9206; i) J. Ezquerra, C. Pedregal, C. Lamas, J. Barluenga, M. Pérez, M. A. García-Martín, J. M. González, J. Org. Chem. 1996, 61, 5804-5812; j) B. C. Söderberg, J. A. Shriver, J. Org. Chem. 1997, 62, 5838-5845; k) F. E. Ziegler, M. Y. Berlin, Tetrahedron Lett. 1998, 39, 2455-2458.
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51. For recent examples of different transformations involving transfer of iodonium ions from this reagent, see: a) G. Espuña, G. Arsequell, G. Valencia, J. Barluenga, J. M. Álvarez-Gutiérrez, A. Ballesteros, J. M. Gonzalez, Angew. Chem. 2004, 116, 329-333; Angew. Chem. Int. Ed. 2004, 43, 325-329; b) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, J. Am. Chem. Soc. 2004, 126, 3416-3417.
52. For recent examples of different transformations involving transfer of iodonium ions from this reagent, see: a) G. Espuña, G. Arsequell, G. Valencia, J. Barluenga, J. M. Álvarez-Gutiérrez, A. Ballesteros, J. M. Gonzalez, Angew. Chem. 2004, 116, 329-333; Angew. Chem. Int. Ed. 2004, 43, 325-329; b) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, J. Am. Chem. Soc. 2004, 126, 3416-3417.
53. For recent examples of different transformations involving transfer of iodonium ions from this reagent, see: a) G. Espuña, G. Arsequell, G. Valencia, J. Barluenga, J. M. Álvarez-Gutiérrez, A. Ballesteros, J. M. Gonzalez, Angew. Chem. 2004, 116, 329-333; Angew. Chem. Int. Ed. 2004, 43, 325-329; b) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, J. Am. Chem. Soc. 2004, 126, 3416-3417.
54. At present, other alternatives such as the reaction of A and the alkene to access C directly cannot be firmly ruled out. Further work is in progress to attempt to ascertain this process.
55. Adapted from L. W. Knight, J. W. Huffman, M. L. Isherwood Synlett 2003, 1993-1996.
56. Recently, after our initial disclosure of the key iodonium-triggered transformation, it was shown that for a related preparation of naphthalenes, iodine could be alternatively used as iodonium donor: D. Yue, N. D. Cà, R. C. Larock, Org. Lett. 2004, 6, 1581-1584.
57. Trace amounts of a compound, likely arising from a crotonic-type condensation process between the enamine and the aldehyde, were also present in the crude reaction mixture.