Generation and intramolecular reactivity of acyl radicals from alkynylthiol esters under reducing tin-free conditions

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1313-1316

  Benati, Luisa ^a   Calestani, Gianluca ^b   Leardini, Rino ^a   Minozzi, Matteo ^a   Nanni, Daniele ^a   Spagnolo, Piero ^a   Strazzari, Samantha ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; ESTER DERIVATIVE; RADICAL; SULFUR; THIOL DERIVATIVE; THIOPHENOL DERIVATIVE; TIN;

ARTICLE; CHEMICAL BOND; CYCLIZATION; MOLECULAR DYNAMICS; SYNTHESIS;

EID: 0141740710     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034252r     Document Type: Article

References (28)

1. (a) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol 4, pp 715-777, 779-831.
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3. (c) Renaud, P.; Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001.
4. For recent reviews on the chemistry of acyl radicals and their application in synthesis, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1051. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
5. For recent reviews on the chemistry of acyl radicals and their application in synthesis, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1051. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
6. For recent reviews on the chemistry of acyl radicals and their application in synthesis, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1051. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
7. For very recent examples of the use of selenoesters in acyl radical chemistry, see: (a) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (b) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. Org. Lett. 2001, 3, 1697. (c) Bennasar, M.-L.; Roca, T.; Griera, R.; Bassa, M.; Bosch, J. J. Org. Chem. 2002, 67, 6268.
8. For very recent examples of the use of selenoesters in acyl radical chemistry, see: (a) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (b) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. Org. Lett. 2001, 3, 1697. (c) Bennasar, M.-L.; Roca, T.; Griera, R.; Bassa, M.; Bosch, J. J. Org. Chem. 2002, 67, 6268.
9. For very recent examples of the use of selenoesters in acyl radical chemistry, see: (a) Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887. (b) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. Org. Lett. 2001, 3, 1697. (c) Bennasar, M.-L.; Roca, T.; Griera, R.; Bassa, M.; Bosch, J. J. Org. Chem. 2002, 67, 6268.
10. For very recent productions of acyl radicals from acyl hydrazine precursors, see: (a) Braslau, R.; Anderson, M. O.; Rivera, F.; Jimenez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513. (b) Bath, S.; Laso, N. M.; Lopez-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204.
11. For very recent productions of acyl radicals from acyl hydrazine precursors, see: (a) Braslau, R.; Anderson, M. O.; Rivera, F.; Jimenez, A.; Haddad, T.; Axon, J. R. Tetrahedron 2002, 58, 5513. (b) Bath, S.; Laso, N. M.; Lopez-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204.
12. For a peculiar use of thiol esters in acyl radical chemistry, see: Ozaki, S.; Yoshinaga, H.; Matsui, E.; Adachi, M. J. Org. Chem. 2001, 66, 2503.
13. (a) Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566.
14. (b) Crich, D.; Hao, X. J. Org. Chem. 1997, 62, 5982.
15. Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S.; Zanardi, G. Org. Lett. 2002, 4, 3079.
16. (a) Benati, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1 1991, 2103.
17. (b) Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1 1995, 1305.
18. (c) Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818.
19. (d) Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1995, 60, 7941.
20. Thiol 11 has recently been prepared from 4-pentyn-1-ol by means of a similar three-step procedure, but no experimental details have been furnished (see: Journet, M.; Rouillard, A.; Cai, D.; Larsen, R. D. J. Org. Chem. 1997, 62, 8630); compound 11 has also been previously prepared from 1-chloro-4-pentyne through hydrolysis of the derived thiuronium salt (see: Dupuy, C.; Crozet, M. P.; Surzur, J. M. Bull. Soc. Chim. Fr. 1980, Part 2, 353).
21. Thiol 11 has recently been prepared from 4-pentyn-1-ol by means of a similar three-step procedure, but no experimental details have been furnished (see: Journet, M.; Rouillard, A.; Cai, D.; Larsen, R. D. J. Org. Chem. 1997, 62, 8630); compound 11 has also been previously prepared from 1-chloro-4-pentyne through hydrolysis of the derived thiuronium salt (see: Dupuy, C.; Crozet, M. P.; Surzur, J. M. Bull. Soc. Chim. Fr. 1980, Part 2, 353).
22. Cyclized ketones 12 and 13 were obtained by Crich in strictly comparable yields when the same aroyl radical was generated from the iodothiol ester precursor (see ref 4a).
23. Chromanone 15 was obtained by Crich in a similar yield when the same aroyl radical was generated from the iodothiol ester precursor (see ref 4a).
24. 2-Indolylacyl radicals have very recently been generated from selenoesters, aldehydes, and α-keto acids and used in intermolecular additions to alkenes (see ref 3b).
25. Amount of the resulting vinyl sulfide adduct was not diminished when an alkanethiol such as 1-butanethiol or methyl thioglycolate was used instead of benzenethiol.
26. Data of the X-ray crystallographic analysis of compound 25 are included in Supporting Information.
27. 3SiH even though sulfur-hydrogen bonds in the alkanethiols are relatively strong (see: Newcomb, M.; Glenn, A. G.; Manek, M. B. J. Org. Chem. 1989, 54, 4603. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188).
28. 3SiH even though sulfur-hydrogen bonds in the alkanethiols are relatively strong (see: Newcomb, M.; Glenn, A. G.; Manek, M. B. J. Org. Chem. 1989, 54, 4603. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188).