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

ABSTRACT: 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.

SUBMITTER: Silva-Cuevas C

PROVIDER: S-EPMC9092473 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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

Silva-Cuevas Carolina C Paleo Ehecatl E León-Rayo David F DF Lujan-Montelongo J Armando JA

RSC advances 20180710 43

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. ...[more]

PMID: 35557855

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