Silver Acetate Mediated Acetoxylations of Alkyl Halides

Roberto Nolla-Saltiel; Ulises Alonso Carrillo-Arcos; Susana Porcel

doi:10.1055/s-0033-1338551

Synthesis, Table of Contents

Synthesis 2014; 46(02): 165-169
DOI: 10.1055/s-0033-1338551

practical synthetic procedures

Silver Acetate Mediated Acetoxylations of Alkyl Halides

Roberto Nolla-Saltiel

Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, 04510 México D.F., México Fax: +52(55)56162217 Email: sporcel@unam.mx

,

Ulises Alonso Carrillo-Arcos

Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, 04510 México D.F., México Fax: +52(55)56162217 Email: sporcel@unam.mx

,

Susana Porcel*

Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, 04510 México D.F., México Fax: +52(55)56162217 Email: sporcel@unam.mx

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Abstract

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Abstract

Silver acetate promotes the acetoxylation of alkyl halides under neutral reaction conditions. The reaction is applicable to primary and activated secondary alkyl halides, and 2,2-dibromoacetophenones for preparing the corresponding acetates in good yields. The presence of ester, amide, nitrile, hydroxy, and OTBDMS functions on the substrate is tolerated.

Key words

alkyl halides - substitution - acetoxylation - silver acetate - isomerization

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References

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Supporting Information