2,3-Difunctionalization of quinones: a gold-catalyzed cascade approach for trifluoromethyl-amination or sulfoximination.

Sharma, Alpa; Govande, Vijaya; Mahajan, Shivangani; Sawant, Sanghapal D

Sharma, Alpa; Govande, Vijaya; Mahajan, Shivangani; Sawant, Sanghapal D.

Afiliación

Sharma A; Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-180001, India.
Govande V; Academy of Scientific and Industrial Research, Ghaziabad-201002, India.
Mahajan S; Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-180001, India.
Sawant SD; Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-180001, India.

Chem Commun (Camb) ; 60(71): 9598-9601, 2024 Aug 29.

Article en En | MEDLINE | ID: mdl-39143950

ABSTRACT

ABSTRACT

A one-pot domino protocol employing gold(I) catalysis has been developed for the cascade trifluoromethyl-amination/sulfoximination of quinones. Togni I serves as the trifluoromethyl installing precursor, while amine or sulfoximine serves as the aminating source. Preliminary investigations suggest a mutual activation of Togni I and the amine precursor, facilitating the facile difunctionalization of quinones with excellent regioselectivity. Extensive substrate scope exploration demonstrates moderate to good yields of difunctionalized products. Application to the natural product Juglone highlights its potential for late-stage modifications in medicinal chemistry and drug discovery.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: India Pais de publicación: Reino Unido

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