Visible light-mediated radical addition cascade cyclization of aryl isocyanides with tricarbonyls: rapid access to substituted phenanthridines and isoquinolines.

Manna, Sabyasachi; Sreedhara, Rahul Halanuru; Prabhu, Kandikere Ramaiah

Manna, Sabyasachi; Sreedhara, Rahul Halanuru; Prabhu, Kandikere Ramaiah.

Afiliación

Manna S; Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India. prabhu@iisc.ac.in.
Sreedhara RH; Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India. prabhu@iisc.ac.in.
Prabhu KR; Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India. prabhu@iisc.ac.in.

Org Biomol Chem ; 2024 Sep 05.

Article en En | MEDLINE | ID: mdl-39235450

ABSTRACT

ABSTRACT

A visible light-mediated synthesis of substituted phenanthridines and isoquinolines from ortho-substituted aryl isocyanides and tricarbonyl compounds is unveiled via the radical addition cascade cyclization (RACC) strategy. This acid/base-free method involves an oxidant (a persulphate salt) and a Ru-photocatalyst. This protocol avoids the use of halogenated compounds as pre-functionalized carbonyl precursors. The products can be easily post-modified to other important small molecules. The functional group tolerance of the reaction and the yields of the products are good without any scalability issues. The mechanistic investigation suggested the presence of a radical pathway during the reaction.

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

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