Aerobic Oxidative C-H Olefination of Arylamides with Unactivated Olefins via a Rh(III)-Catalyzed C-H Activation.

Jambu, Subramanian; Shambhavi, Chikkabagilu Nagaraju; Jeganmohan, Masilamani

Jambu, Subramanian; Shambhavi, Chikkabagilu Nagaraju; Jeganmohan, Masilamani.

Afiliación

Jambu S; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
Shambhavi CN; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
Jeganmohan M; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.

Org Lett ; 23(8): 2964-2970, 2021 04 16.

Article en En | MEDLINE | ID: mdl-33818094

RESUMEN

An efficient Rh(III)-catalyzed aerobic oxidative C-H alkenylation of arylamides with unactivated alkenes is described. The olefination reaction was compatible with various substituted arylamides including primary, secondary, and tertiary as well as functionalized unactivated olefins. Meanwhile, ortho mono/bis-alkylated arylamides were synthesized in the reaction of arylamides with norbornene. In the alkenylation reaction, molecular oxygen along with organic acid was used to regenerate the active catalyst for the next catalytic cycle. A possible reaction mechanism involving C-H activation/insertion/ß-hydride elimination followed by aerobic oxidation was proposed and supported by the deuterium labeling studies.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2021 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos

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