Iodine-Induced Reaction Cascades for the Rapid Construction of Variously Substituted Benzothiophenes

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4377-4380

  Hessian, Karl O ^a   Flynn, Bernard L ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIOPHENE DERIVATIVE; IODINE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; STEREOCHEMISTRY;

EID: 0344496783     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035663a     Document Type: Article

References (27)

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8. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
9. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
10. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
11. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
12. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
13. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
14. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
15. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
16. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
17. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
18. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
19. For reviews see a-e: (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2193. (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 2, p 2227. (d) Cacchi, S.; Fabrizi, G. ; Goggiomani, A. Heterocycles 2002, 56, 613. (e) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432. (g) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042. (h) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035. (i) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905. (j) Yue, D.; Larock, R. C. Abstracts of Papers, 223rd ACS National Meeting; Orlando, Florida, USA, April 7-11; American Chemical Society: Washington, DC, 2002. (k) Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607. (l) Arcadi, A.; Cacchi, S.; Di Guiseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409. (m) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
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