Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 13, Pages 4853-4856Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5007838
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Funding
- NIH/NIGMS [GM-106210]
- Sigma-Aldrich
- SIOC/Zhejiang Medicine Co./Pharmaron
- JSPS
- Grants-in-Aid for Scientific Research [12J10137] Funding Source: KAKEN
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A practical C H functionalization method for the methylation of heteroarenes is presented. Inspiration from Nature's methylating agent, S-adenosylmethionine (SAM), allowed for the design and development of zinc bis(phenylsulfonylmethanesulfinate), or PSMS. The action of PSMS on a heteroarene generates a (phenylsulfonyl)methylated intermediate that can be easily separated from unreacted starting material. This intermediate can then be desulfonylated to the methylated product or elaborated to a deuteriomethylated product, and can divergently access medicinally important motifs. This mild, operationally simple protocol that can be conducted in open air at room temperature is compatible with sensitive functional groups for the late-stage functionalization of pharmacologically relevant substrates.
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