Efficient synthesis of thioesters and amides from aldehydes by using an intermolecular radical reaction in water

Chemistry - A European Journal

Volumn 11, Issue 2, 2005, Pages 719-727

  Nambu, Hisanori ^a   Hata, Kayoko ^a   Matsugi, Masato ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Amidation; Radical reactions; Surfactants; Thioesters

Indexed keywords

ALDEHYDES; ESTERIFICATION; REACTION KINETICS; SURFACE ACTIVE AGENTS; SYNTHESIS (CHEMICAL);

AMIDATION; CETYLTRIMETHYL-AMMONIUM BROMIDE (CTAB); REACTION MIXTURES; THIOESTERS;

ESTERS;

2,2' AZOBIS[2 (2 IMIDAZOLIN 2 YL)PROPANE]; ALDEHYDE DERIVATIVE; AMIDE; BENZENE DERIVATIVE; CETRIMIDE; ESTER DERIVATIVE; PROPANE; SURFACTANT; THIOESTER; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; AMIDATION; ARTICLE; ESTERIFICATION; MOLECULAR INTERACTION; RADICAL REACTION; REACTION ANALYSIS; SOLUBILITY; SYNTHESIS;

ALDEHYDES; AMIDES; CETRIMONIUM COMPOUNDS; ESTERS; INDICATORS AND REAGENTS; SPECTROPHOTOMETRY, INFRARED; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; WATER;

EID: 12444342979     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400754     Document Type: Article

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33. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
34. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
35. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
36. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
37. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
38. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
39. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
40. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
41. Some recent reports: a) R. K. Jr., Boeckman, T. J. Clark, B. C. Shook, Org. Lett. 2002, 4, 2109-2112; b) D. A. Longbottom, A. J. Morrison, D. J. Dixon, S. V. Ley, Angew. Chem. 2002, 114, 2910-2914; Angew. Chem. Int. Ed. 2002, 41, 2786-2790; c) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895; d) D. A. Evans, H. A. Rajapakse, A. Chiu, D. Stenkamp, Angew. Chem. 2002, 114, 4755-4758; Angew. Chem. Int. Ed. 2002, 41, 4573-4576; e) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 6552-6554; f) V. K. Aggarwal, B. N. Esquivel-Zamora, J. Org. Chem. 2002, 67, 8618-8621; g) K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737-1740; h) R. Ingenito, H. Wenschuh, Org. Lett. 2003, 5, 4587-4590; i) J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151.
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82. The yields of these thioesterifications were affected by the electron density of the functional groups of aldehydes. It is reasonable to suppose that the acyl radical intermediate of the thioesterification is stabilized by electrical effects. That is, the acyl radical formed from the aliphatic aldehyde or aromatic aldehyde with an electron-releasing substituent would be stabilized by the captodative effect. On the other hand, the acyl radical formed from the aromatic aldehyde with an electron-withdrawing substituent would not be stabilized, therefore, the thioesterification with 1j and 1k did not proceed at all; cf. captodative effect: L. Stella, J. N. Harvey, in Radicals in Organic Synthesis, Vol. 1 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, pp. 360-380. (Equation Presented)
83. It is possible that this thioesterification proceeds via the nucleophilic addition of the thiyl radical to the aldehyde. Namely, the thiyl radical produced by the disulfide nucleophilically attacks the carbonyl group of the aldehyde, and then the alkoxyl radical (X) is formed. Next, the hydride radical is eliminated from the alkoxyl radical intermediate (X), and the thioesterification is achieved. If this thioesterification will proceed via this plausible reaction mechanism, the aldehydes with an electron-withdrawing substitute (1j, 1k) should be nucleophilically attacked by the thiyl radical. However, these thioesterification with 1j and 1k did not proceed at all (Table 4, entries 10, 11). In addition, the alkyl or aryl radical is more stable than the hydride radical, therefore, it is difficult that the hydride radical eliminates from the alkoxyl radical intermediate (X). Accordingly, it might be inferred from this reactivity that this thioesterification is achieved via the acyl radical intermediate (Scheme 1). (Equation Presented)
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