DTBB-catalysed lithiation of chlorinated benzylic chlorides, alcohols, thiols or amines

Tetrahedron

Volumn 54, Issue 9, 1998, Pages 1853-1866

  Gómez, Cecilia ^a   Huerta, Fernando F ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; BENZYL CHLORIDE; BIPHENYL DERIVATIVE; LITHIUM; THIOL DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHLORINATION; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032568036     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10402-1     Document Type: Article

References (19)

1. 1. See, for instance: Wakefield, B. J. Organolithium Methods, Academic Press: London, 1988.
2. 2. (a) Akiyama, S.; Hooz, J. Tetrahedron Lett. 1973, 4115-4118.
3. (b) Schlenk, W.; Holtz, J. Ber. Dtsch. Chem. Ger. 1917, 50, 262-274.
4. (c) Guijarro, D.; Mancheño, B.; Yus, M. Tetrahedron 1992, 48, 4593-4600.
5. 3. (a) For a monograph, see: Blomberg, C. The Barbier Reaction and Related One-step Processes; Springer-Verlag: Berlin, 1993.
6. (b) Alonso, F.; Yus, M. Recent Res. Devel. Org. Chem., in press.
7. 4. (a) See reference 3a pp. 79 and 83.
8. (b) For a recent paper on the use of 2-bromobenzyl bromide for benzylic coupling by bromine/lithium exchange, see: Warren, S.; Wyatt, P.; McPartlin, M.; Woodroffe, T. Tetrahedron Lett. 1996, 37, 5609-5612.
9. 5. (a) For the first account on this reaction, see: Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For a recent review, see: Yus, M. Chem. Soc. Rev. 1996, 155-161.
10. 5. (a) For the first account on this reaction, see: Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400. For a recent review, see: Yus, M. Chem. Soc. Rev. 1996, 155-161.
11. 6. For the last paper on this topic from our laboratory, see: Guijarro, A.; Yus, M. Tetrahedron 1996, 52, 1797-1810.
12. 7. For a preliminary communication, see: Gómez, C.; Huerta, F. F.; Yus, M. Tetrahedron Lett. 1997, 38, 687-690.
13. 8. For the preparation of the equivalent magnesiated o-derivative (1-magnesacyclobutabenzene), see: de Boer, H. J. R.; Akkerman, O. S.; Bickelhaupt, F. Organometal. Synth. 1988, 4, 396-398.
14. 9. Under the reaction condition (-50°C), the nuclear Cl/Li exchange works very slowly, so for short reaction times (ca. 20 min), no aromatic lithiation was observed; we never found reaction products in which the electrophile was attached to the aromatic ring for the two-step process. See, also: Guijarro, A.; Ramón, D. J.; Yus, M. Tetrahedron 1993, 49, 469-482.
15. rd edn.; Pergamon Press: Oxford, 1988.
16. 11. For this product was not possible to obtain the corresponding HRMS due to its decomposition.
17. + signal.
18. 13. When amines 6 were used as starting materials, an acidic-basic work-up gave essentially pure products 8.
19. 14. Almena, J. ; Foubelo, F. ; Yus, M. Tetrahedron 1995, 51, 3351-3364.