One carbon homologation of halides to benzyl ethers

Tetrahedron Letters

Volumn 50, Issue 21, 2009, Pages 2462-2463

  Taber, Douglass F ^a   Paquette, Craig M ^a   Reddy, P Ganapati ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AROMATIC COMPOUND; BENZYL ETHER DERIVATIVE; BROMINE DERIVATIVE; CARBON; ETHER DERIVATIVE; GRIGNARD REAGENT; HALIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; PURIFICATION; ROOM TEMPERATURE;

EID: 63749128759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.010     Document Type: Article

References (18)

1. Shimojo M., Matsumoto K., and Hatanaka M. Tetrahedron 56 (2000) 9281
2. For the one recorded example of a Grignard reagent (derived from propargyl bromide) coupling with BOM-Cl, see:. Aliev A.K., Karaev S.F., and Gasanov K.G. Nauch. Tr. Azerb. In-ta Nefti i Khimii (1979) 59
3. Several instances of enolate alkylation with BOM-Cl have been reported. Kende A.S., and Chen J. J. Am. Chem. Soc. 107 (1985) 7184
4. Lee B.H., Biswas A., and Miller M.J. J. Org. Chem. 51 (1986) 106
5. Brooks D.W., Kellogg R.P., and Cooper C.S. J. Org. Chem. 52 (1987) 192
6. Fujisawa T., Fujimura A., and Sato T. Bull. Chem. Soc. Jpn. 61 (1988) 1273
7. Corey E.J., and Yuen P.W. Tetrahedron Lett. 30 (1989) 5825
8. Soti F., Kajtar-Peredy M., Keresztury G., Incze M., Kardos-Balogh Z., and Szantay C. Tetrahedron 47 (1991) 271
9. Mata E.G., and Thomas E.J. J. Chem. Soc., Perkin Trans. 1 (1995) 785
10. Blakemore P.R., Browder C.C., Hong J., Lincoln C.M., Nagornyy P.A., Robarge L.A., Wardrop D.J., and White J.D. J. Org. Chem. 70 (2005) 5449
11. For the alkylation of the anion derived by deprotonation of a methyl pyridine with BOM-Cl, see:. Leighton P., and Sanders J.K.M. J. Chem. Soc., Perkin Trans. 1 (1987) 2385
12. For the conversion of BOM-Cl into the Grignard reagent and coupling with an electrophile, see:. Crich D., and Banerjee A. J. Am. Chem. Soc. 128 (2006) 8078
13. For a previous preparation of 2c, see:. Smith E.H., and Jeropoulos S. J. Chem. Soc., Chem. Commun. (1986) 1621
14. For a previous preparation of 2d, see:. Barluenga J., Alonso-Cires L., Campos P., and Asensio G. Synthesis (1983) 53
15. For synthetic applications of 2c, see:. Poulter C.D., and Muehlbacher M. J. Org. Chem. 53 (1988) 1026
16. Legraverend M., Boumchita H., Zerial A., Huel C., Lemaitre M., and Bisagni E. J. Med Chem. 33 (1990) 2476
17. Chan K., Ling Y.H., and Loh T. Chem. Commun. (2007) 939
18. 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methine carbons as 'd' and for methylene and quaternary carbons as 'u'.