Halobenzyl ethers as protecting groups for organic synthesis [18]

Journal of the American Chemical Society

Volumn 122, Issue 29, 2000, Pages 7148-7149

  Plante, Obadiah J ^a   Buchwald, Stephen L ^a   Seeberger, Peter H ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; ETHER DERIVATIVE; HALIDE;

AMINATION; CATALYSIS; CHEMICAL REACTION; HALOGENATION; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034718086     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0008665     Document Type: Letter

References (14)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1999.
2. Yan, L.; Kahne, D. E. Synlett 1995, 523-524.
3. Jobron, L.; Hindsgaul, O. J. Am. Chem. Soc. 1999, 121, 5835-5836.
4. Initial studies with PBB, PCB in peptide synthesis: Yamashiro, D. J. Org. Chem. 1977, 42, 523-525. PCB in oligosaccharide synthesis: Pohl, N. L.; Kiessling, L. L. Tetrahedron Lett. 1997, 38, 6985-6988.
5. Initial studies with PBB, PCB in peptide synthesis: Yamashiro, D. J. Org. Chem. 1977, 42, 523-525. PCB in oligosaccharide synthesis: Pohl, N. L.; Kiessling, L. L. Tetrahedron Lett. 1997, 38, 6985-6988.
6. (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
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8. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
9. Cost analysis of substituted benzyl halides: 4-chlorobenzyl chloride ($0.10/g), 4-bromobenzyl bromide ($0.70/g), 4-iodobenzyl bromide ($10/g).
10. Wolfe, J. P.; Tomori, H.; Yin, I.; Sadighi, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
11. The coupling with n-hexylamine resulted in the formation of a significant amount of the bis-arylation product.
12. Please see Supporting Information for details of the preparation of 10 and 19-24.
13. Mayer, T. G.; Kratzer, B.; Schmidt, R. R. Angew. Chem., Int. Ed. 1994, 33, 2177-2180.
14. Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211-214.