A simple one-pot procedure for the direct conversion of alcohols to azides via phosphate activation

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1959-1961

  Yu, Chengzhi ^a   Liu, Bin ^a   Hu, Longqin ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000351719     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060376     Document Type: Article

References (14)

1. (a) Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis; 1991; Pergamon Press: New York, Vol. VI, pp 76-79.
2. (b) Hanessian S. Preparative Carbohydrate Chemistry; Marcel Dekker: New York, 1997, Chapter 5, pp 90-97.
3. (a) Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679-680.
4. (b) Hughes, D. L. Org. React. 1992, 42, 358-359.
5. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1977, 60, 417-425.
6. Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 1977-1980.
7. Viaud, M. C.; Rollin, P. Synthesis 1990, 130-132.
8. Thompson, A. S.; Humphrey, G. R.; Demarco, A. M.; Mathre, D. J.; Grabowski, J. J. J. Org. Chem. 1993, 58, 5886-5888.
9. Shioriri, T.; Yamada, S. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, pp 206-207.
10. Caution: Azides especially bisazidated products are potentially explosive and should be handled with care. The procedure should be performed in a well-ventilated hood.
11. 3) data for the azide products listed in Table 1: δ ppm 11: 8.14 (d, J = 8.4 Hz, 2H), 7.60-7.52 (m. 4H), 7.39-7.29 (m 8H), 4.83 (t, J = 5.8 Hz, 1H), 3.80-3.69 (m, 1H), 3.58-3.50 (m. 1H), 1.94-1.80 (m, 2H). 1.10 (s, 9H); 12: 8.22 (dd, J= 1.8, 6.8 Hz, 2H), 7.52 (dd, J = 0.3. 6.9 Hz, 2H), 4.83 (dd. J = 4.5, 9.0 Hz, 1H), 4.60 (d, J = 69 Hz. 1H), 0.4.51 (d. J= 1.2. 6.8 Hz, 1H), 3.51-3.40 (m, 2H), 3.37 (s, 3H) 2.07-2.02 (m, 1H), 1.93-1.89 (m, 1H); 13: 7.40-7.32 (m, 4H), 4.69 (d, J = 5.9 Hz. 2H), 4.45 (s. 2H), 2.52 (t, J = 5.9 Hz, 1H); 14: 7.68 (d J = 8.0 Hz, 1H), 7.53 (t, J = 7.1 Hz. 1H), 7.38 (t, J = 7.9 Hz, 2H). 3.53 (t, J = 7.3 Hz, 2H), 3.10 (t, J = 7.3 Hz, 2H); 15: 7.69 (d, J = 7.7 Hz. 4H), 7.50-7.32 (m, 10H), 4.80 (s, 2H), 4.34 (s, 2H), 1.09 (s, 9H); 16: 7.73-7.69 (m, 4H), 7.48-7.42 (m, 6H). 3.79 (t, J = 5.9 Hz, 2H), 3.49 (t, J = 6.8 Hz, 2H), 1.85 (p, J = 6.3 Hz, 2H), 1.10 (s, 9H); 17: 7.78-7.73 (m, 4H), 7.49-7.43 (m, 6H), 3.75 (t, J = 6.1 Hz, 2H), 3.29 (t, J = 6.8 Hz, 2H), 1.69-1.55 (m, 6H), 1.14 (s, 9H); 18: 7.75-7.70 (m, 4H), 7.46-7.42 (m. 6H), 3.72 (t, J = 6.2 Hz, 2H), 3.28 (t, J = 6.9 Hz, 2H), 1.64-1.58 (m. 4H), 1.43-1.37 (m, 6H), 1.11 (s, 9H).
12. Guha, A. K.; Lee, W.; Lee, I. J. Org. Chem. 2000, 65, 12-15.
13. The mechanism of phosphoryl transfer from phosphate monoesters and diesters has been the subject of many recent investigations. See: Thatcher, G. R. J.; Luger, R. K. Adv. Phys. Org. Chem. 1989, 25, 99-103 and references therein.
14. For example, sodium cyanide might be used in place of sodium azide to convert alcohols to the corresponding chain extended nitriles in a similar "one-pot" procedure.