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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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:
Chemistry
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
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author Silva-Cuevas, Carolina
Paleo, Ehecatl
León-Rayo, David F.
Lujan-Montelongo, J. Armando
author_facet Silva-Cuevas, Carolina
Paleo, Ehecatl
León-Rayo, David F.
Lujan-Montelongo, J. Armando
author_sort Silva-Cuevas, Carolina
collection PubMed
description 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.
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spelling pubmed-90924732022-05-11 An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks Silva-Cuevas, Carolina Paleo, Ehecatl León-Rayo, David F. Lujan-Montelongo, J. Armando RSC Adv Chemistry 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. The Royal Society of Chemistry 2018-07-10 /pmc/articles/PMC9092473/ /pubmed/35557855 http://dx.doi.org/10.1039/c8ra04002h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Silva-Cuevas, Carolina
Paleo, Ehecatl
León-Rayo, David F.
Lujan-Montelongo, J. Armando
An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
title An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
title_full An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
title_fullStr An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
title_full_unstemmed An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
title_short An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
title_sort expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092473/
https://www.ncbi.nlm.nih.gov/pubmed/35557855
http://dx.doi.org/10.1039/c8ra04002h
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