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An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks

A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant...

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Detalles Bibliográficos
Autores principales: Silva-Cuevas, Carolina, Paleo, Ehecatl, León-Rayo, David F., Lujan-Montelongo, J. Armando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092473/
https://www.ncbi.nlm.nih.gov/pubmed/35557855
http://dx.doi.org/10.1039/c8ra04002h
Descripción
Sumario:A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant applicability while bromo-lithium exchange and functionalization sequences, free radical reductions, and additions of the title compounds demonstrate their synthetic utility.