Synthesis of 3-hydroxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate as a versatile intermediate in preparative organic chemistry

Synthesis of 3-hydroxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate as a versatile intermediate in preparative organic chemistry

Moreira, Bárbara V.; Raminelli, Cristiano

Abstract:

Owing to the considerable importance of benzyne as highly reactive intermediate in organic chemistry, with applications in total syntheses and in preparations of functional materials, we intend to synthesize the 3-hydroxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (6), envisioning the employment of such aryne precursor in reactions of insertion into sigma bonds, in cycloaddition reactions and in the total synthesis of bioactive natural products.

Owing to the considerable importance of benzyne as highly reactive intermediate in organic chemistry, with applications in total syntheses and in preparations of functional materials, we intend to synthesize the 3-hydroxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (6), envisioning the employment of such aryne precursor in reactions of insertion into sigma bonds, in cycloaddition reactions and in the total synthesis of bioactive natural products.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201391593549

Referências bibliográficas

• [1] 1 (a) Tadross, P. M.; Stoltz B. M. Chem. Rev. 2012, 122, 3550. (b) Gampe, C. M.; Carreira, E. M. Angew. Chem. Int. Ed. 2012, 41, 2766.
• [2] 2 Guitián, E.; Pérez, D. Peña, D. Top. Organomet Chem. 2005, 14, 109.
• [3] 3 Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827.
• [4] 4 Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley And Sons: New York, 1999, 3a Ed.

Como citar:

Moreira, Bárbara V.; Raminelli, Cristiano; "Synthesis of 3-hydroxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate as a versatile intermediate in preparative organic chemistry", p-101-101. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201391593549