C-H methylation of heteroarenes inspired by radical SAM methyl transferase.
J Am Chem Soc
; 136(13): 4853-6, 2014 Apr 02.
Article
en En
| MEDLINE
| ID: mdl-24611732
ABSTRACT
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.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Compuestos Organometálicos
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S-Adenosilmetionina
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Ácidos Sulfínicos
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Zinc
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Hidrocarburos Aromáticos
Tipo de estudio:
Guideline
Idioma:
En
Revista:
J Am Chem Soc
Año:
2014
Tipo del documento:
Article
País de afiliación:
Estados Unidos